JP2864698B2 - Optically active aromatic compound having a trifluoromethyl group, method for producing the same, liquid crystal composition containing the same as an active ingredient, and liquid crystal element using the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

TECHNICAL FIELD The present invention relates to a novel organic compound, a method for producing the same, a liquid crystal composition containing the same as an active ingredient, and a liquid crystal device using the same. More specifically, the compounding of a ferroelectric liquid crystal composition The present invention relates to an optically active aromatic compound having a trifluoromethyl group useful as a component, a method for producing the compound, a liquid crystal composition containing the compound as an active ingredient, and a liquid crystal device using the same. <Prior Art> At present, a TN (twisted nematic) type display system is most widely used as a liquid crystal display device. This TN liquid crystal display has many advantages such as low driving voltage and low power consumption. However, in terms of response speed, it is inferior to light-emitting display devices such as cathode-ray tubes, electroluminescence, and plasma displays. A new TN display device with a twist angle of 180 to 270 ° has been developed, but the response speed is still inferior. Although various improvements have been made as described above, a TN type display element having a high response speed has not been realized. However, a new display system using a ferroelectric liquid crystal, which has been actively studied recently, has a possibility of remarkably improving the response speed (Clark et al .; Applid Phys. Le).
tt., 36 , 899 (1980)). This method uses a chiral smectic phase such as a chiral smectic C phase (hereinafter, abbreviated as Sc * phase) exhibiting ferroelectricity. It is known that not only the Sc * phase but also chiral smectic F, G, H, and I phases exhibit ferroelectricity. Many properties are required for ferroelectric liquid crystal materials used in ferroelectric liquid crystal display elements actually used, but at present, a single compound cannot satisfy such properties, It is necessary to use a ferroelectric liquid crystal composition obtained by mixing a liquid crystal compound or a non-liquid crystal compound. Further, not only a ferroelectric liquid crystal composition comprising only a ferroelectric liquid crystal compound, but also Japanese Patent Application Laid-Open No. 61-195187 discloses non-chiral smectic C, F, G, H, I phases (hereinafter referred to as Sc). The compound and the composition exhibiting a ferroelectric liquid crystal phase may be mixed with one or more compounds exhibiting a ferroelectric liquid crystal phase to form a whole as a ferroelectric liquid crystal composition. It has been reported. Furthermore, a compound or composition exhibiting a phase such as Sc is used as a basic substance, and one or more compounds that are optically active but do not exhibit a ferroelectric liquid crystal phase are mixed to form a ferroelectric liquid crystal composition as a whole. (Mol. Cryst. Liq. Cryst. 89 , 327)
(1982)). Taken together, it can be seen that one or more of the optically active compounds can be mixed with the basic substance to form a ferroelectric liquid crystal composition regardless of whether or not it exhibits a ferroelectric liquid crystal phase. However, the optically active substance preferably exhibits a liquid crystal phase if desired, and when the optically active substance does not exhibit a liquid crystal phase, it is desirable that the structure is similar to a liquid crystal compound, that is, a pseudo liquid crystal substance. However, a liquid crystal material having a spontaneous polarization required for high-speed response, a low viscosity, and a liquid crystal phase in a lower temperature range has not been found so far. <Problems to be Solved by the Invention> In view of the above, the present invention provides a ferroelectric liquid crystal material having a sufficient spontaneous polarization, capable of high-speed response, and exhibiting a liquid crystal phase in a lower temperature range. The purpose is to: <Means for Solving the Problems> The present invention provides a compound represented by the general formula [1]: (Wherein, R ¹ represents an alkyl group having 3 to 20 carbon atoms, and R ² represents an alkyl group or an alkoxyalkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom. K is 0 or 1 And n represents an integer of 0 to 5, and p represents 0 or 1.
Is shown. Ar is Or Is shown. Y represents -O-, -COO- or -OCO-. X
Represents -COO- when n is 0, and -COO- or -OCO- when n is an integer of 1 to 5. * Indicates an asymmetric carbon atom. The present invention provides an optically active aromatic compound having a trifluoromethyl group represented by the formula (1), a method for producing the compound, a liquid crystal composition containing the compound as an active ingredient, and a liquid crystal element using the same. Among the aromatic compound (1) having a trifluoromethyl group according to the present invention, compounds wherein X is -COO- in which the general formula (2) R ¹ Y _k Ar-COR '(2) (In the formula, R ¹ , K, Ar and Y represent the same meaning as described above.
R 'represents a hydroxyl group or a halogen atom. And a carboxylic acid compound represented by the general formula [3]: (Wherein, R ² , n, p and * have the same meanings as described above). The compound can be produced by reacting with an optically active phenol derivative in the presence of a catalyst or a condensing agent. Examples of the carboxylic acid compound [2] include 4-alkoxybenzoic acid, 4-alkylbenzoic acid, 4-alkoxycarbonylbenzoic acid, 4-alkylcarbonyloxybenzoic acid, 4′-alkoxy-4-biphenylcarboxylic acid,
4'-alkyl-4-biphenylcarboxylic acid, 4'-alkoxycarbonyl-4-biphenylcarboxylic acid, 4 '
-Alkylcarbonyloxy-4-biphenylcarboxylic acid, 2- (4-hydroxycarbonylphenyl) -5
Alkoxypyrimidine, 2- (4-hydroxycarbonylphenyl) -5-alkylpyrimidine, 2- (4-hydroxycarbonylphenyl) -5-alkoxycarbonylpyrimidine, 2- (4-hydroxycarbonylphenyl) -5-alkylcarbonyloxypyrimidine These carboxylic acids can be used as an acid halide, that is, an acid chloride, an acid bromide, or the like. Here, the alkyl or alkoxy has an alkyl group R ¹ having 3 to 20 carbon atoms, and specific examples of the alkyl group include propyl, butyl, pentyl,
Hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl,
Nonadecyl and eicosyl are exemplified. On the other hand, as the optically active phenol derivative [3], for example, 4-
(1-alkoxy-2,2,2-trifluoroethyl) phenol, 4- (2-alkoxy-3,3,3-trifluoropropyl) phenol, 4- (3-alkoxy-4,4,4
-Trifluorobutyl) phenol, 4- (4-alkoxy-5,5,5-trifluoropentyl) phenol, 4
-(5-alkoxy-6,6,6-trifluorohexyl)
Phenol, 4- (6-alkoxy-7,7,7-trifluoroheptyl) phenol and the like. In addition, compounds in which alkoxyalkoxy, alkylcarbonyloxy or alkoxyalkylcarbonyloxy is used instead of alkoxy in the above examples are also exemplified. Here, the above-mentioned alkoxy, alkoxyalkoxy, alkylcarbonyloxy and alkoxyalkylcarbonyloxy are represented by the general formula [3]. And the substituent R ² is an alkyl group or an alkoxyalkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, and these alkyl groups or alkoxyalkyl groups are linear or branched. In the case of a branched structure, it may be an optically active group. Specific examples of the above alkyl group or alkoxyalkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, Nonadecyl, eicosyl, methoxymethyl,
Methoxyethyl, methoxypropyl, methoxybutyl,
Methoxypentyl, methoxyhexyl, methoxyheptyl, methoxyoctyl, methoxynonyl, methoxydecyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, ethoxybutyl, ethoxypentyl, ethoxyhexyl, ethoxyheptyl, ethoxyoctyl, ethoxynonyl, ethoxydecyl, propoxymethyl , Propoxyethyl, propoxypropyl, propoxybutyl, propoxypentyl, propoxyhexyl, propoxyheptyl, propoxyoctyl, propoxynonyl, propoxydecyl, butoxymethyl, butoxyethyl, butoxypropyl, butoxybutyl, butoxypentyl, butoxyhexyl, butoxyheptyl Octyl, butoxynonyl, butoxydecyl, pentyloxymethyl, pentyl Shiechiru, pentyloxy propyl, pentyl oxy butyl, pentyl oxy pentyl,
Pentyloxyhexyl, pentyloxyoctyl, pentyloxydecyl, hexyloxymethyl, hexyloxyethyl, hexyloxypropyl, hexyloxybutyl, hexyloxypentyl, hexyloxyhexyl, hexyloxyoctyl, hexyloxynonyl, hexyloxydecyl, heptyloxy Methyl, heptyloxyethyl, heptyloxypropyl, heptyloxybutyl, heptyloxypentyl, octyloxymethyl, octyloxyethyl, octyloxypropyl, decyloxymethyl, decyloxyethyl, decyloxypropyl, 1-methylethyl, 1-methyl Propyl, 1-methylbutyl, 1-methylpentyl, 1-
Methylhexyl, 1-methylheptyl, 1-methyloctyl, 2-methylethyl, 2-methylbutyl, 2,3-dimethylbutyl, 2,3,3-trimethylbutyl, 2-methylpentyl, 3-methylpentyl, 2, 3-dimethylpentyl, 2,4-dimethylpentyl, 2,3,3,4-tetramethylpentyl, 2-methylhexyl, 3-methylhexyl, 4
-Methylhexyl, 2,5-dimethylhexyl, 2-methylheptyl, 2-methyloctyl, 2-trihalomethylpentyl, 2-trihalomethylhexyl, 2-trihalomethylhexyl, 2-haloethyl, 2-halopropyl,
3-halopropyl, 3-halo-2-methylpropyl, 2,
3-dihalopropyl, 2-halobutyl, 3-halobutyl, 4-halobutyl, 2,3-dihalobutyl, 2,4-dihalobutyl, 3,4-dihalobutyl, 2-halo-3-methylbutyl, 2-halo-3,3- Dimethylbutyl, 2-halopentyl, 3-halopentyl, 4-halopentyl, 5-halopentyl, 2,4-dihalopentyl, 2,5-dihalopentyl, 2-halo-3-methylpentyl, 2-halo-4-methylpentyl, 2 -Halo-3-monohalomethyl-4-methylpentyl, 2-halohexyl, 3-halohexyl,
4-halohexyl, 5-halohexyl, 6-halohexyl, 2-haloheptyl, 2-halooctyl (however, halo in the above alkyl group represents fluorine, chlorine, bromine or iodine). Further, when p is 1, in addition to the above substituents, halomethyl, 1-haloethyl, 1-halopropyl, 1-halobutyl, 1-halopentyl, 1-halohexyl,
Haloheptyl, 1-halooctyl and the like can be mentioned. The reaction between the carboxylic acid compound [2] and the optically active phenol derivative [3] can be carried out in the presence or absence of a solvent by applying a usual esterification method. When a solvent is used in this reaction, examples of the solvent include aliphatic solvents such as tetrahydrofuran, ethyl ether, acetone, methyl ethyl ketone, toluene, benzene, chlorobenzene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, dimethylformamide, hexane and pyridine. Alternatively, a solvent which is inert to the reaction of an aromatic hydrocarbon, an ether, a halogenated hydrocarbon, an organic amine, or the like, alone or in a mixture. The amount can be used without any particular limitation. In this reaction, since the optically active phenol derivative [3] is relatively expensive, it is preferable to carry out the reaction using an excess amount of the carboxylic acid compound [2], which is the partner material, and usually 1 to 4 equivalents, More preferably, 1 to 2 equivalents are used. Examples of the catalyst include dimethylaminopyridine, triethylamine, tri-n-butylamine, pyridine,
Picoline, collidine, imidazole, sodium carbonate,
Organic or inorganic basic substances such as sodium methylate and potassium bicarbonate can be mentioned. Further, an organic acid or an inorganic acid such as toluenesulfonic acid, methanesulfonic acid or sulfuric acid can be used as a catalyst. The amount of the catalyst used varies depending on the type of each reaction raw material used and the combination of the catalyst used, etc., and cannot always be specified. For example, when an acid halide is used, the amount of the basic compound is at least one equivalent of the acid halide. The substance is used. When the carboxylic acid compound represented by the general formula [2] is a carboxylic acid, carbodiimides such as N, N'-dicyclohexylcarbodiimide and N-cyclohexyl-N '-(4-diethylamino) cyclohexylcarbodiimide are condensed. It is preferably used as an agent, and if necessary, an organic base such as 4-pyrrolidinopyridine, pyridine or triethylamine can be used in combination. The amount of the condensing agent used in this case is usually 1 to 1.2 equivalent times with respect to the optically active phenol derivative [3]. When an organic base is used in combination, the amount used is usually
It is 0.01 to 0.2 equivalent times. The reaction temperature of the reaction between the carboxylic acid compound [2] and the optically active phenol derivative [3] is usually from -30 ° C to 10 ° C.
The temperature is 0 ° C, more preferably -25 ° C to 80 ° C, and the reaction time is not particularly limited. After completion of the reaction, the desired optically active aromatic compound having a trifluoromethyl group represented by the general formula [1] (where X is- COO-) can be isolated. This can be further purified, if necessary, by operations such as column chromatography and recrystallization. The optically active phenol derivative [3] as a raw material can be produced, for example, by any one of the following methods. (1) Manufacturing method when n is 0. (Wherein, R ² , p and * have the same meanings as described above;
Represents a chlorine atom, a bromine atom or an iodine atom, and R ³ represents a lower alkyl group. Hereinafter, each step will be specifically described. The Grignard reaction in the first step is a step of reacting a Grignard reagent represented by the general formula [4] with trifluoroacetic acid or a derivative thereof to obtain a trifluoroacetophenone derivative represented by the formula [5]. The Grignard reagent [4] can be produced from the corresponding halogenobenzene derivative and magnesium. Specific examples of trifluoroacetic acid or a derivative thereof used in this reaction include, in addition to trifluoroacetic acid, halogenated trifluoroacetyls such as trifluoroacetyl chloride and trifluoroacetyl bromide, methyl trifluoroacetate, and trifluoroacetic acid. Esters such as ethyl fluoroacetate, N
Acid amides such as trifluoroacetylimidazole,
Examples thereof include trifluoroacetic anhydride. The amount of these trifluoroacetic acids or derivatives thereof used is the same as in Grignard reagent [4] except for trifluoroacetic acid.
1 equivalent or more, and usually in the range of 1 to 3 equivalents. When trifluoroacetic acid is used, the Grignard reagent [4] is used in an amount of 2 equivalents or more based on 1 equivalent of trifluoroacetic acid, and the reaction is usually performed in a range of 2 to 4 equivalents. Examples of the solvent include ethers such as ethyl ether and tetrahydrofuran, and aromatic hydrocarbons such as benzene, toluene and xylene, alone or in a mixture. The amount of these solvents is not particularly limited. The reaction temperature is usually -120 ° C to 0 ° C, preferably -100 ° C.
C. to -20C. The reaction time is not particularly limited. The removal of the trifluoroacetophenone derivative [5] from the reaction mixture is performed by, for example, adding ordinary post-treatment operations such as extraction, separation, concentration and recrystallization, or column chromatography. The second step is a step of reducing the trifluoroacetophenone derivative [5] to obtain a β-phenethyl alcohol derivative represented by the formula [6]. In this reduction reaction, a reducing agent for reducing ketone to alcohol is used, and examples of such a reducing agent include lithium aluminum hydride, sodium borohydride, and borohydride. The reducing agent is used in an amount of 1 equivalent or more based on the trifluoroacetophenone derivative [5] as a raw material, and is usually used in an amount of 1 to 10 equivalents. This reduction reaction is carried out in a solvent. Examples of such a solvent include ethers such as tetrahydrofuran, dioxane and ethyl ether, alcohols such as methanol, ethanol, n-propyl alcohol and isopropyl alcohol, and aromatic hydrocarbons such as toluene and benzene. Examples thereof include hydrogens, halogenated hydrocarbons such as chloroform and dichloromethane, and the like, alone or in combination. The reaction is usually carried out at -30C to 100C, preferably at -20C to 9C.
Perform at 0 ° C. The end point of the reaction is usually determined when the trifluoroacetophenone derivative [5] disappears from the reaction system. The removal of the β-phenethyl alcohol derivative [6]
For example, it is performed by adding ordinary post-treatment operations such as extraction, liquid separation, and concentration. The third step is a β-phenethyl alcohol derivative [6]
Is acylated with a carboxylic acid represented by the general formula [10] R ³ COOH [10] (wherein R ³ has the same meaning as described above) or a derivative thereof in a solvent in the presence of a catalyst; 7] is a process for producing an ester. As the carboxylic acid [10] or a derivative thereof, for example, acetic acid, propionic acid, acetic anhydride, propionic anhydride, acetic chloride or bromide, propionic chloride or bromide, butyryl chloride or bromide,
Valeroyl chloride or bromide. These are used in an amount of 1 equivalent or more with respect to the β-phenethyl alcohol derivative [6], and the upper limit is not particularly limited, but is preferably 4 equivalents. The acylation is carried out in the presence of a catalyst, which includes:
For example, dimethylaminopyridine, triethylamine,
Organic or inorganic base materials such as tri-n-butylamine, pyridine, picoline, imidazole, sodium carbonate, sodium methylate, potassium hydrogen carbonate and the like can be mentioned. Further, acids such as toluenesulfonic acid, methanesulfonic acid, and sulfuric acid can be used as the catalyst. Although the amount of use is not particularly limited, it is usually 1 to 5 equivalents with respect to the β-phenethyl alcohol derivative [6]. In this acylation reaction, examples of the solvent used include aliphatic or aromatic solvents such as tetrahydrofuran, ethyl ether, acetone, methyl ethyl ketone, hexane, toluene, benzene, chlorobenzene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, dimethylformamide, and pyridine. Solvents which are inert to the reaction, such as aromatic hydrocarbons, ethers, halogenated hydrocarbons, aprotic polar solvents and organic amines, alone or in a mixture. The amount used is not particularly limited. When an organic amine is used as a solvent, the amine may act as a catalyst. The reaction temperature is usually -30C to 100C, preferably -20C to 9C.
Performed at 0 ° C. The reaction time is not particularly limited, and the time when the raw material β-phenethyl alcohol derivative [6] has disappeared can be regarded as the end point of the reaction. The ester [7] is removed by subjecting the reaction mixture to a usual separation means, for example, a post-treatment operation such as extraction, liquid separation, concentration, and recrystallization. The fourth step is to asymmetrically hydrolyze the ester [7] using an esterase having an ability to preferentially hydrolyze only one of the optical isomers of the ester [8] This is a step of producing an optically active alcohol compound represented by the formula: As the esterase used in this asymmetric hydrolysis reaction, an enzyme obtained from an animal, a plant, or a microorganism is used.
As its use form, purified enzyme, crude enzyme, enzyme-containing material, microbial culture solution, culture, bacterial cells, culture filtrate and those obtained by treating them can be used as needed in various forms, Microorganisms can be used in combination. Alternatively, it can be used as an immobilized enzyme immobilized on a resin or the like, or an immobilized cell. Here, esterase means esterase in a broad sense including lipase. The microorganism that produces an esterase used in the asymmetric hydrolysis reaction may be any microorganism that produces an esterase having the ability to asymmetrically hydrolyze esters [7], and is not particularly limited. Specific examples of such microorganisms include, for example, Enterobacter, Arthrobacter, Previbacterium, Pseudomonas, Alcaligenes, Micrococcus, Chromobacterium, Microbacterium, Corynebacterium, Bacillus, Lactobacillus, Trichoderma, Candida, Saccharomyces, Rhodotorula, Cryptococcus, Torulopsis, Pichia, Penicillium, Aspergillus,
Microorganisms belonging to the genera Rhizopus, Mucor, Aureopacidium, Actinomucor, Nocardia, Streptomyces, Hansenula, and Achromobacter are exemplified. The cultivation of the microorganism is usually performed according to a conventional method, and a culture solution can be obtained by performing liquid culture. For example, a sterilized liquid medium [for molds and yeasts, malt extract / yeast extract medium (5 g of peptone, 10 g of glucose, 3 g of malt extract, 3 g of yeast extract and 3 g of yeast extract in 1 L of water, pH
6.5), for bacteria, inoculated with microorganisms in a sweetened broth medium (10 g of glucose, 5 g of peptone, 5 g of meat extract, and 3 g of NaCl dissolved in 1 L of water and adjusted to pH 7.2), usually at 20 to 40 ° C.
Is performed by reciprocating shaking culture for 1 to 3 days,
If necessary, solid culture may be performed. Some of these microbial esterases are commercially available and can be easily obtained. Specific examples of commercially available esterases include, for example, the following. Pseudomonas lipase [lipase P (manufactured by Amano Pharmaceutical)], Aspergillus lipase [lipase AP (manufactured by Amano Pharmaceutical)], Mucor lipase [lipase M-AP]
(Manufactured by Amano Pharmaceutical Co., Ltd.)), lipase of Candida syrindrasse [lipase MY (manufactured by Meito Sangyo)], lipase of the genus Alcaligenes [lipase PL (manufactured by Meito Sangyo)], lipase of the genus Achromobacter [lipase AL (name Sugar industry)),
Lipase of the genus Arthrobacter [lipase joint BSL (joint liquor purification)], lipase of the genus Chromobacterium (manufactured by Toyo Brewery), lipase of Rhizopus delemar [talipase (manufactured by Tanabe Seiyaku)], lipase of the genus Rhizopus [lipase syrup] Ken (Osaka Bacteria Research Institute)]. In addition, animal / plant esterases can also be used, and specific examples of these esterases include the following. Steapsin, pancreatin, pig liver esterase, Wheat Cerm esterase. The asymmetric hydrolysis reaction is usually carried out by vigorously stirring a mixture of the starting ester [7] and the above enzyme or microorganism in a buffer solution. As the buffer, sodium phosphate which is usually used,
A buffer solution of an inorganic acid salt such as potassium phosphate, a buffer solution of an organic acid salt such as sodium acetate or sodium citrate or the like is used, and the pH thereof is preferably 8 to 11 in a culture solution of an alkaliphilic bacterium or an alkaline esterase. PH 5 to 8 is preferable for a culture solution of a non-alkaline microorganism or an esterase having no alkali resistance. The concentration is usually in the range of 0.05-2M, preferably 0.05-0.5M. The reaction temperature is usually from 10 to 60 ° C, and the reaction time is generally from 10 to 70 hours, but is not limited thereto. When a lipase belonging to the genus Pseudomonas or Arthrobacter is used as the lipase in this asymmetric hydrolysis reaction, an optically active alcohol compound [8] with relatively high optical purity can be obtained. In addition, at the time of this asymmetric hydrolysis, an organic solvent which is inert to the reaction, such as toluene, chloroform, methyl isobutyl ketone, or dichloromethane, can be used in addition to the buffer solution. The reaction can be performed advantageously. By such an asymmetric hydrolysis reaction, only one of the optical isomers of the raw material esters [7] is preferentially hydrolyzed, and an optically active alcohol compound represented by the formula [8] is produced. The other optical isomer remains as an asymmetric hydrolysis residue as an ester compound. The removal of the optically active alcohol compound [8] from the reaction mixture is carried out by subjecting the reaction mixture to a usual post-treatment, for example, extraction with a solvent such as ethyl acetate, evaporating the solvent from the obtained organic layer, and then removing the concentrated residue. By column chromatography or the like. In this way, an optically active alcohol compound [8] as an asymmetric hydrolysis product and an optically active ester represented by the general formula [7] as an asymmetric hydrolysis residue are obtained. The optically active esters remaining as the hydrolysis residue are further hydrolyzed, if necessary, to give an enantiomeric optically active alcohol compound [8] from that obtained in the asymmetric hydrolysis reaction. be able to. In the fifth step, the optically active alcohol compound [8] is acylated or alkylated to form a compound represented by the general formula

This is a step of obtaining an optically active benzyloxybenzene derivative represented by [9]. General formula

The optically active benzyloxybenzene derivative represented by [9] and p is 1 is an optically active alcohol compound [8] and a general formula [11] R ² COOH [11] (wherein R ² is And a carboxylic acid represented by the following formula or a derivative thereof in the presence of a catalyst or a condensing agent. Specific examples of the substituent R ² in the general formula [11] include the same alkyl group or alkoxyalkyl group as the substituent R ² in the optically active phenol derivative represented by the general formula [3]. In this acylation reaction, a carboxylic acid having a substituent R ² of the above acid halide such as an acid anhydride or acid chloride or acid bromide is used. These carboxylic acids or derivatives thereof may be racemic or optically active, and when the carboxylic acid is optically active, some of them are oxidized with the corresponding alcohol or reduced with amino acids. Some can be derived from optically active amino acids or optically active oxyacids as shown below, which are obtained by selective deamination and which are either naturally occurring or obtained by resolution. Alanine, valine, leucine, isoleucine, phenylalinine, serine, threonine, alosreonine, homoserine, alloisoleucine, tert-leucine, 2-aminobutyric acid, norvaline, norleucine, ornithine, lysine, hydroxylysine, phenylglycine, trifluoroalanine , Aspartic acid, glutamic acid, lactic acid,
Mandelic acid, tropic acid, 3-hydroxybutyric acid, malic acid, tartaric acid, isopropylmalic acid and the like. The reaction of such a carboxylic acid or a derivative thereof with the optically active alcohol compound represented by the formula [8] is performed in the presence or absence of a solvent. Examples of the solvent include tetrahydrofuran, ethyl ether, acetone, methyl ethyl ketone, toluene,
Solvents which are inert to the reaction of aliphatic or aromatic hydrocarbons such as benzene, chloroform, chlorobenzene, dichloromethane, dichloroethane, carbon tetrachloride, dimethylformamide, hexane, etc., ethers, ketones, amides or halogenated hydrocarbons, alone or in a mixture. And
The amount used is not particularly limited. When an acid anhydride or an acid halide is used in this reaction, the reaction is performed using a catalyst. The amount of the acid anhydride or acid halide to be used is 1 equivalent or more relative to the optically active alcohol compound [8], and the upper limit is not particularly limited, but is preferably 4 equivalents or less. Examples of the catalyst include dimethylaminopyridine, triethylamine, tri-n-butylamine, picoline,
Examples thereof include organic or inorganic basic substances such as imidazole, sodium carbonate, and potassium hydrogen carbonate, and organic or inorganic acids such as toluenesulfonic acid, methanesulfonic acid, and sulfuric acid. The amount of the catalyst to be used is not particularly limited. For example, when an acid halide is used, the amount is at least one equivalent to the acid halide. When a carboxylic acid represented by the general formula [11] is used in the reaction, the reaction is performed using a condensing agent. The amount of the carboxylic acid to be used is usually 1 to 2 equivalents relative to the optically active alcohol compound [8]. As the condensing agent, carbodiimides such as N, N'-dicyclohexylcarbodiimide and N-cyclohexyl-N '-(4-diethylamino) cyclohexylcarbodiimide are preferably used, and if necessary, organic solvents such as 4-pyrrolidinopyridine, pyridine and triethylamine. A base is used in combination. The amount of the condensing agent used is 1 to 1.
When the organic base is used, the amount used is 0.01 to 0.2 equivalent times with respect to the condensing agent. The reaction is usually -80 ° C to 120 ° C, preferably -20 ° C to 90 ° C
It is done in. The reaction time is not particularly limited, and the time when the optically active alcohol compound [8] disappears from the reaction system can be regarded as the reaction end point. General formula

In [9], removal of the optically active benzyloxybenzene derivative in which p is 1 from the reaction mixture is performed by a usual post-treatment operation such as extraction, liquid separation, concentration, recrystallization or column chromatography. This is done by: General formula

In [9], the optically active benzyloxybenzene derivative in which p is 0 can be prepared by reacting an optically active alcohol compound [8] with a compound of the general formula [1] in the presence of a basic substance in a solvent.
2] R ² -Z [12] (wherein, R ² has the same meaning as described above, and Z represents a halogen atom or —OSO 2 R ″. Here, R ″ is a lower alkyl group or an optionally substituted phenyl. The compound can be produced by alkylating with an alkylating agent represented by the formula: Here, as the basic substance, sodium hydride, alkali metal hydride such as potassium hydride, sodium hydroxide, potassium hydroxide, alkali metal hydroxide or alkaline earth metal such as calcium hydroxide, sodium carbonate, Alkali metal carbonates such as potassium carbonate,
Examples thereof include butyllithium and the like, and alkali metals such as lithium, sodium and potassium. Such a basic substance is used in an amount of 1 equivalent or more with respect to the optically active alcohol compound [8], and the upper limit is not particularly limited, but is preferably used in an amount of 1 to 5 equivalents. The alkylating agent [12] used in this reaction is a halide such as chloride, bromide, iodide or the like having an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, or a sulfonic acid. Esters (methanesulfonic acid ester, ethanesulfonic acid ester, benzenesulfonic acid ester, toluenesulfonic acid ester, etc.). The specific examples of the substituents R ² in the alkylating agent (12) is the same as substituent R ² in the optically active phenol derivative represented by general formula [3]. These alkylating agents [12] can be easily produced from the corresponding alcohol if necessary. Further, the substituent R ² in the alkylating agent [12] may be an optically active group, and the alkylating agent having such an optically active group (halide or sulfonic acid ester) may be a corresponding optically active alcohol if necessary. Synthesized from Certain of the optically active alcohols are readily obtained by asymmetric metal catalysis of the corresponding ketones or by asymmetric reduction by microorganisms or enzymes. Some are naturally occurring or can be derived from optically active amino acids and optically active oxy acids obtained by resolution, such as: Valine, leucine, isoleucine, phenylalanine, threonine, alosreonine, homoserine, alloisoleucine, tert-leucine, 2-aminobutyric acid, norvaline,
Norleucine, ornithine, lysine, hydroxylysine, phenylglycine, aspartic acid, glutamic acid, mandelic acid, tropic acid, 3-hydroxybutyric acid, malic acid, tartaric acid, isopropyl malic acid and the like. The amount of such an alkylating agent [12] to be used is optionally 1 equivalent or more times the optically active alcohol compound [8], but is usually 1 to 5 equivalents. As the reaction solvent, for example, tetrahydrofuran, ethers such as ethyl ether, acetone, ketones such as methyl ethyl ketone, toluene, aromatic hydrocarbons such as benzene, chloroform, dichloromethane, halogenated hydrocarbons such as dichloroethane or chlorobenzene,
Aliphatic hydrocarbons such as pentane and hexane, and polar solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphorylamide and N-methylpyrrolidone can be used. Reaction temperature is usually −50 ° C. to 120 ° C., preferably −80 ° C.
Performed at ~ 100 ° C. The reaction time is not particularly limited, but is usually the general formula [8]
The point at which the optically active alcohol compound represented by the above disappears from the reaction system can be regarded as the reaction end point. General formula

In [9], removal of the optically active benzyloxybenzene derivative having p = 0 from the reaction mixture may be carried out by a usual post-treatment operation such as extraction, liquid separation, concentration, recrystallization or column chromatography. This is done by: The sixth step is an optically active benzyloxybenzene derivative

In this step, [9] is debenzylated in the presence of a hydrogenation catalyst and hydrogen to obtain the desired optically active phenol derivative in which n is 0 in the general formula [3]. Examples of the hydrogenation catalyst used in this debenzylation reaction include platinum-based catalysts such as PtO ₂ and Pt-C or Pd-C, Pd-BaSO
₄₁ Palladium such as palladium black or Rh-C, Rh-
Rhodium-based catalysts such as Al ₂ O ₃ , ruthenium-based catalysts such as RuO ₂ and Ru—C, and nickel-based catalysts such as Raney nickel can be used, and palladium-based catalysts are more preferably used. The hydrogenation catalyst has the general formula

It is usually used in an amount of 0.01 to 100% by weight, preferably 0.1 to 50% by weight, based on the optically active benzyloxybenzene derivative represented by [9]. As the solvent, methanol, alcohols such as ethanol, dioxane, ethers such as tetrahydrofuran,
Benzene, aromatic hydrocarbons such as toluene, n-hexane, aliphatic hydrocarbons such as cyclohexane, esters such as ethyl acetate, amides such as dimethylformamide,
Examples thereof include fatty acids such as acetic acid and the like, and water alone and mixtures thereof. The hydrogen pressure in the reaction is usually 1 to 200 atm. The reaction temperature is usually 0 to 200 ° C, more preferably 20 to 180 ° C. The reaction time varies depending on the type of the hydrogenation catalyst, the reaction temperature and the hydrogen pressure, and is not particularly limited.

Optically active benzyloxybenes represented by [9]
Dissipation of zen derivative from reaction system or termination of hydrogen absorption
Is determined by Represented by the general formula [3] from the reaction mixture, and n is 0
The removal of the optically active phenol derivative is
Concentration, recrystallization, distillation or column chromatography, etc.
Is performed by adding the usual post-processing operation of (2) In the optically active phenol derivative [3], n is
A production method when an integer of 1 to 5 is indicated. (Where R^Two, R^Three, A, p and * have the same meanings as described above.
Represents, R^FourIs a hydrogen atom or -COR^ThreeIs shown. Hereinafter, each step will be described. The Grignard reaction in the first step is represented by the general formula [13].
Grignard reagent and trifluoroacetic acid or its derivative
React with a conductor to form a ketone compound of the general formula [14]
This is the step of obtaining a product. Grignard reagent [13] is the corresponding ω-halogenoa
Can be manufactured from rutile benzene and magnesium
You. This reaction is based on the optically active phenol derivative
In the same reaction as in the first step in the production method (1) of [3]
Yes, the reaction and post-treatment
The ketone compound [14] can be obtained. In the second step, the ketone compound [14] is reduced to give a compound of the general formula
In the step of producing an alcohol compound represented by (15),
You. This reduction reaction is carried out by the above-mentioned optically active phenol derivative.
In the same reaction as in the second step in the production method (1) of [3],
Yes, the reaction and after-treatment
Thus, an alcohol compound [15] can be obtained. In the third step, the alcohol compound [15] is converted to a compound represented by the general formula
The carboxylic acid represented by [10] or a derivative thereof
Silylated to obtain an ester compound represented by the general formula [16].
This is the process of This acylation reaction is based on the above-mentioned optically active phenol induction.
The same reaction as in the third step of the production method (1) of the conductor [3] is performed.
By performing the reaction and post-treatment according to it,
An ester compound [16] can be obtained. In the fourth step, the ester compound [16] is
Acylation by acylation reaction yields an acyl group represented by the general formula [17].
This is a step of obtaining a cetophenone derivative. Acylating agent used in this Friedel-Crafts reaction
Acetic acid, acetyl chloride or acetyl bromide
Acetic acid such as amide or a derivative thereof;
Dosage should be 1 equivalent or more for ester compound [16]
The upper limit is not particularly limited, but is usually 3
Equivalent times. In this reaction, a catalyst is used.
Aluminum chloride, aluminum bromide,
Lead, zinc bromide, titanium tetrachloride, polyphosphoric acid, trifluoride
Examples include urine. The amount of the catalyst used is usually the amount of the ester compound [16]
In the range of 0.3 to 3 equivalent times. The reaction temperature is -30 ° C to 150 ° C, preferably -10 to 100 ° C.
is there. The reaction time is not particularly limited, and the starting ester compound
The reaction can be terminated when [16] disappears. Removal of acetophenone derivative [17] from reaction mixture
The usual post-treatment operations such as extraction, separation and concentration
Can be performed by operations such as contraction, etc.
Further purification by operations such as chromatography
Can also be. In the fifth step, the acetophenone derivative [17] is
Only one of the optical isomers of the tophenone derivative
Esterase that has the ability to preferentially hydrolyze
And represented by the general formula [18] by asymmetric hydrolysis.
This is a step of obtaining an optically active acetophenone derivative. In this reaction, the above-mentioned optically active phenol derivative [3]
Of the same reaction and post-treatment as in the fourth step of the production method (1)
By applying the matter to the acetophenone derivative [17]
Represented by the general formula [18] as an asymmetric hydrolysis product,
And R^FourActive Acetophenone Derivatives where A is a Hydrogen Atom
Can be obtained as an asymmetric hydrolysis residue of the general formula [1
8] and R^FourIs −COR^ThreeIs an optically active aceto
A phenone derivative can be obtained. The sixth step is an optically active acetophenone derivative [18]
Is oxidized by barrier barrier liger to give the general formula [19]
This is a step of obtaining an optically active acetoxybenzene derivative.
You. As an oxidizing agent used for this barrier bilger oxidation
Stands for peracetic acid, formic acid, m-chloroperbenzoic acid, perbenzoic acid
Examples are peracids such as acids. Such peracids are, for example, corresponding
Acid and hydrogen peroxide
The reaction can be carried out while generating peracid in the reaction. The amount of peracid used depends on the optically active acetophenone derivative
It is used at least 1 equivalent times [18].
Although not particularly limited, it is usually 2 equivalent times. In this reaction, a solvent inert to the reaction is usually used.
Such solvents include dichloromethane and dichloromethane.
Luethane, chloroform, chlorobenzene, benzene,
C, such as toluene, xylene, hexane, and cyclohexane
Hydrogenated hydrocarbons, aromatic or aliphatic hydrocarbons, etc.
A single compound or a mixture is exemplified. The amount of such solvent used is
There is no particular limitation. The reaction temperature is usually -20 to 130 ° C, preferably -10 to 1
00 ° C. The reaction time is not particularly limited.
Termination of reaction upon disappearance of phenone derivative [18]
Can be. Optically active acetoxybenzene derivation from reaction mixtures
Removal of body [19] can be, for example, removal of excess peracid, extraction
This should be done by ordinary post-treatment operations such as extraction, separation and concentration.
Column chromatography, if necessary
It can also be purified by an operation such as-. The seventh step is an optically active acetoxybenzene derivative
[19] is hydrolyzed to give an optical activity represented by the general formula [20].
This is a step of obtaining an acidic diol. This reaction uses an acid or alkali in the presence of water.
It is done. As the acid used here, for example, sulfuric acid, phosphorus
Inorganic acids such as acid and hydrochloric acid or toluenesulfonic acid,
Organic acids such as tansulfonic acid can be mentioned. Sodium hydroxide, potassium hydroxide
Medium, barium hydroxide, potassium carbonate, sodium carbonate
Or 1,8-diazabicyclo [5,4,0] 7-undecene
Inorganic and organic bases are included. The amount of such acid or alkali used is as follows
is there. Acids react with optically active acetoxybenzene derivatives [19]
And usually used in the range of 0.02 to 10 equivalent times,
Li has an optically active acetoxybenzene derivative [19]
R^FourWhen is a hydrogen atom, at least one equivalent^FourIs −COR^Three
In the case of, it is necessary to use 2 equivalent times or more.
Is not particularly limited, but is usually 10 equivalent times. The above reaction is usually performed in the presence of an organic solvent. Such solvents include methanol, ethanol, pro
Panol, acetone, methyl ethyl ketone, chloroform
System, dichloromethane, toluene, xylene, hexane,
Heptane, ethyl ether, tetrahydrofuran, geo
Xane, dimethylformamide, N-methylpyrrolidone
Such as aliphatic or aromatic hydrocarbons, ethers, and alcohols
Of alcohols, ketones, amides or halogenated hydrocarbons
Correspondingly inert solvents are exemplified, and these solvents are used alone.
Or mixed. The amount used is not particularly limited. Reaction temperature is usually −30 ° C. to 150 ° C., preferably −20 ° C.
~ 100 ° C. The reaction time is not particularly limited.
The reaction is terminated when the xylene derivative [19] disappears.
Can be Removal of optically active diols [20] from reaction mixture
For example, conventional post-treatments such as acid precipitation, extraction, liquid separation, concentration, etc.
It can be performed by adding a logical operation. In the eighth step, the optically active diols [20] are converted to the general formula [2]
3](Wherein, A has the same meaning as described above.)
Obtaining an optically active alcohol represented by the general formula [21]
It is a process. This reaction is usually performed in the presence of a basic substance.
Such basic substances include sodium carbonate and potassium carbonate.
Alkali metal carbonates, sodium hydroxide, potassium hydroxide
Alkali metal hydroxides such as lithium, sodium methyla
Metal alcohol such as sodium and sodium ethylate
Is exemplified. The amount of such a basic substance to be used depends on the amount of the optically active diols.
It is used in an amount of 1 equivalent or more based on [20], and usually 1 to 5 equivalents.
Used twice. As the reaction solvent, for example, tetrahydrofuran, dihydrofuran
Oxane, ethyl ether, acetone, methyl ethyl ke
Ton, dimethylformamide, dimethylsulfoxide,
Solvents inert to the reaction such as N-methylpyrrolidone
Or mixtures are used. Use of benzyl halide [23] used in this reaction
The dose should be at least 1 equivalent to the diols [20].
The upper limit is not particularly limited.
It is usually 5 equivalent times. The reaction temperature is usually -20 ° C to 150 ° C, preferably
Is from 0 to 130 ° C. The reaction time is not particularly limited, and the optically active
The reaction can be terminated by the disappearance of
You. After completion of the reaction, usual separation means such as extraction, liquid separation,
Optically active alcohols [21] are obtained by operations such as concentration.
This can be used for column chromatography if necessary.
Further purification by procedures such as chromatography and recrystallization
Can also. Ninth step is acylation of optically active alcohols [21]
Or an alkylated optical activity represented by the general formula [22]
This is a step of obtaining a novel benzyloxybenzene derivative. This reaction is carried out by the above-mentioned optically active phenol derivative [3].
Is the same reaction as in the fifth step in the production method (1),
By performing the same reaction and post-treatment,
Benzyloxybenzene derivative [22]
it can. That is, optically active alcohols [21] are represented by the general formula
By the carboxylic acid or a derivative thereof represented by [11]
By acylation, in the general formula [22]), p
Is an optically active benzyloxybenzene derivative
Obtained by the alkylating agent represented by the general formula [12].
By the alkylation, in the general formula [22],
Optically active benzyloxybenzene derivative wherein p is 0
Is obtained. The tenth step is the derivation of optically active benzyloxybenzene.
Compound [22] is debenzylated in the presence of a hydrogenation catalyst and hydrogen.
In the general formula [3], n is an integer of 1 to 5.
This is a step of obtaining an optically active phenol derivative. This reaction is based on the optically active phenol derivative
In the same reaction as in the sixth step in the production method (1) of (3),
Yes, similar reactions and post-treatments
By adding to the ziroxybenzene derivative [22],
In the target general formula [3], n is an integer of 1 to 5
A certain optically active phenol derivative can be produced
You. (3) In the optically active phenol derivative (3), n
Is an integer of 1 to 5 and p is 0.(Where R^TwoAnd * represent the same meaning as described above. ) In the production of the optically active phenol derivative (3),
The production method when n is an integer of 1 to 5 is described above.
As described in the manufacturing method (2), when p is 0,
As long as it is possible, the production shown in the above reaction formula is also possible. Hereinafter, each step will be described. In the first step, an optically active alcohol represented by the general formula [24] is used.
Alkylation of a coal compound represented by the general formula [12]
Optically active compound represented by the general formula [25]
This is a step of obtaining an acetophenone derivative. Optically active alcohol used as a raw material in this reaction
Compound [24] is an optically active phenol derivative
In the asymmetric hydrolysis reaction of the fifth step in the production method (2) of
Represented by the general formula [18] obtained as an asymmetric hydrolysis product,
And R^FourIs the same as a compound in which is a hydrogen atom. In addition, it was obtained as an asymmetric decomposition residue by this asymmetric hydrolysis reaction.
Represented by the general formula [18] and R^FourIs −COR^ThreeIs a compound
If it is further hydrolyzed, it will be converted to an asymmetric hydrolysis product first.
The obtained compound is represented by the general formula [18] having an enantiomeric relationship,
And R^FourIs a hydrogen atom.
With the optically active alcohol compound [24]
It can also be used. This alkylation reaction is carried out by the optically active phenol described above.
General formula in the fifth step of production method (1) of derivative [3]
Alkylation reaction using an alkylating agent represented by [12]
And the same reaction and post-treatment conditions
To apply to optically active alcoholic compounds [24]
Gives an optically active acetophenone derivative [25]
be able to. In addition, the above alkylation reaction is carried out in the presence of a basic substance.
The reaction is carried out in the same manner as in the alkyl represented by the general formula [12].
When the substituent Z of the agent is an iodine atom,
Silver oxide can be used in place of the reactive substance, and the reaction yield
In view of the above, the reaction is more preferable than the reaction performed in the presence of a basic substance. In this case, the amount of silver oxide used is
1 equivalent or more based on Cole Compound [24]
Is not particularly limited, but is preferably 5 equivalents
is there. Use of alkylating agent [12] (substituent Z is iodine atom)
The amount is 1 equivalent to the optically active alcohol compound [24].
The amount is optional, but is usually in the range of 2 to 10 equivalent times.
You. As the reaction solvent, an excess amount of the above alkylating agent [12]
Can also be used. In addition, for example, tetrahydrofuran
Orchid, ethyl ether, dioxane, acetone, methyl
Ethyl ketone, benzene, toluene, hexane, dimethyl
Lformamide, dimethyl sulfoxide, N-methylpi
Ethers, ketones, hydrocarbons or non-pro
Solvents that are inert to the reaction, such as
Mixtures can be used. The reaction temperature is generally 0 to 150 ° C, preferably 20 to 100 ° C.
It is. The reaction time is generally 1 hour to 20 days. After the completion of the reaction, the silver salt is removed by filtration.
Post-treatment, for example, adding operations such as extraction, liquid separation, and concentration
As a result, optically active acetophenone derivatives [25]
Which can be obtained by column chromatography
Further purification can also be performed by such operations. The second step is an optically active acetophenone derivative [25]
Is oxidized by Bayer-Villiger to give the light of general formula [26]
This is a step of obtaining a chemically active acetoxybenzene derivative. This reaction involves the production of an optically active phenol derivative [3].
Bayer Villiger oxidation of the sixth step in the manufacturing method (2)
The reaction is similar, and the reaction and post-treatment are performed according to it.
To produce an optically active acetophenone derivative [26]
Obtainable. The third step is an optically active acetoxybenzene derivative
[26] is hydrolyzed to obtain the desired compound of general formula (3)
Wherein n is an integer of 1 to 5 and p is 0.
This is a step of producing a neutral phenol derivative. This reaction uses an acid or alkali in the presence of water.
It is done. As the acid used here, for example, sulfuric acid, phosphorus
Inorganic acids such as acid and hydrochloric acid or toluenesulfonic acid,
Organic acids such as tansulfonic acid can be mentioned. Sodium hydroxide, potassium hydroxide
, Sodium hydroxide, potassium carbonate, sodium carbonate
Or 1,8-diazabicyclo [5,4,0] 7-undecene, etc.
And inorganic and organic bases. The amount of such acid or alkali used is as follows
is there. Acids react with optically active acetoxybenzene derivatives [26]
And usually used in the range of 0.02 to 10 equivalent times,
Li against optically active acetoxybenzene derivatives [26]
At least one equivalent, and there is no particular upper limit.
However, it is usually 10 equivalent times. The reaction is usually performed in the presence of an organic solvent. Such solvents include methanol, ethanol, pro
Panol, acetone, methyl ethyl ketone, chloroform
System, dichloromethane, toluene, xylene, hexane,
Heptane, ethyl ether, tetrahydrofuran, geo
Xane, dimethylformamide, N-methylpyrrolidone
Such as aliphatic or aromatic hydrocarbons, ethers, and alcohols
Of alcohols, ketones, amides or halogenated hydrocarbons
Correspondingly inert solvents are exemplified, and these solvents are used alone.
Or mixed. The amount used is not particularly limited. Reaction temperature is usually −30 ° C. to 150 ° C., preferably −20 ° C.
~ 100 ° C. The reaction time is not particularly limited.
The reaction can be terminated when the derivative [26] disappears.
Wear. After completion of the reaction, usual post-treatments such as acid precipitation, extraction,
By adding operations such as liquid and concentration,
In the formula (3), n is an integer of 1 to 5, and p is
It is possible to obtain an optically active phenol derivative which is 0
If necessary, add this to column chromatography.
It can be purified by operations such as luffy and recrystallization.
You. Next, aromatization having a trifluoromethyl group of the present invention
Method for producing compound of compound (3) wherein X is -OCO-
Will be described. Of an aromatic compound (3) having a trifluoromethyl group
Among them, the compound in which X is -OCO- is represented by the general formula [27] R¹Y_kAr-OH [27] (wherein, R¹, Y, Ar and k have the same meanings as above.
You. ) And a phenolic compound of the general formula [28](Where R ′, R^Two, P and * represent the same meaning as described above.
N represents an integer of 1 to 5. Catalyzed or condensed with an optically active benzoic acid derivative represented by
It can be manufactured by reacting in the presence of a mixture.
Wear. In the above, the phenolic compound [27] is 4-A
Lucoxyphenol, 4-alkylphenol, 4-a
Lucoxycarbonyl phenol, 4-alkyl carbonyl
Luoxyphenol, 4'-alkoxy-4-hydroxy
Sibiphenyl, 4'-alkyl-4-hydroxybiphe
Nil, 4'-alkoxycarbonyl-4-hydroxybi
Phenyl, 4'-alkylcarbonyloxy-4-hydr
Roxybiphenyl, 2- (4-hydroxyphenyl)-
5-alkoxypyrimidine, 2- (4-hydroxyphene
Nyl) -5-alkylpyrimidine, 2- (4-hydroxy
(Cyphenyl) -5-alkoxycarbonylpyrimidine,
2- (4-hydroxyphenyl) -5-alkylcarbo
Nyloxypyrimidine and the like are exemplified. Here, the above alkyl or alkoxy refers to a carbon atom
Having 3 to 20 alkyl groups R1;
Specific examples of the group include those exemplified above.
You. On the other hand, as an optically active benzoic acid derivative [28],
For example, 4- (2-alkoxy-3,3,3-trifluoroprop
Ropyl) benzoic acid, 4- (3-alkoxy-4,4,4-to
Trifluorobutyl) benzoic acid, 4- (4-alkoxy-
5,5,5-trifluoropentyl) benzoic acid, 4- (5-
Alkoxy-6,6,6-trifluorohexyl) benzoate
Acid, 4- (6-alkoxy-7,7,7-trifluorohep
Chill) benzoic acid and the like. Also, instead of alkoxy in the above example, alkoxy
Alkoxy, alkylcarbonyloxy or alcohol
Compounds with xyalkylcarbonyloxy are also exemplified.
You. In addition, these carboxylic acids react with an acid halide during the reaction.
It is also used as an acid chloride, acid chloride, acid bromide, etc.
It is. Here, the above alkoxy, alkoxyalkoxy, a
Alkylcarbonyloxy and alkoxyalkylcar
Bonyloxy is represented by the formula —O—C—R in the general formula [28].^Two
And the substituent R^TwoIs an alkyl group having 1 to 20 carbon atoms
Or an alkoxyalkyl group,
Or alkoxyalkyl groups are straight-chain or branched
Yes, if it is branched, it may be an optically active group. As the above alkyl group or alkoxyalkyl group
Are those exemplified above. Phenol compound [27] and optically active benzoic acid derivative
The reaction with [28] has a trifluoromethyl group as described above.
Optically active aromatic compound [3] (where X is -COO
-) Can be carried out in the same manner as in the production method. However, relatively expensive optically active benzoic acid derivatives [2
In order to use [8] effectively, phenol which is the partner material
It is preferable to carry out the reaction using an excess amount of compound [27].
And usually 1 to 4 equivalents, more preferably 1 to 2 equivalents
Used. Also, an optically active benzoic acid derivative represented by the general formula [28]
When the conductor is a carboxylic acid, the general formula [3] (provided that X is
Is preferably carbodiimide as in the case of -COO-).
It can be carried out in the same way for reaction conditions, etc.
You. The optically active benzoic acid derivative [28], which is the starting compound,
Manufactured by one of the following two methods
be able to. (1) When p is 0 An optically active compound represented by the general formula [28] and p is 0
Benzoic acid derivatives are the aforementioned optically active phenol derivatives
In the general formula [25] obtained in the production method (3) of [3]
Optically active acetophenone derivative shown in the presence of water
It can be manufactured by oxidizing to In this oxidation reaction, acetyl groups are oxidized to form carboxylic acids.
Is used. Such oxidizing agents include potassium dichromate, bichrom
Sodium oxalate, potassium permanganate, permanganate
Sodium, potassium hypochlorite, sodium hypochlorite
, Potassium hypobromite, sodium hypobromite, etc.
Is shown. The oxidizing agent is optically active acetophenone derivative
It is at least 1 equivalent times the body [25].
Although not particularly limited, preferably used amount of 10 equivalents or less
It is. In this reaction, an organic solvent is used in addition to water
Such solvents include dioxane, tetra
Incompatible with oxidation reactions of hydrofuran, N-methylpyrrolidone, etc.
An active solvent is used. The reaction temperature is usually -20 to 130 ° C, preferably -10 to 1
00 ° C. The reaction time is not particularly limited.
The reaction is terminated when the phenone derivative [25] disappears. After completion of the reaction, usual post-treatments such as acid precipitation, extraction, and liquid separation
By adding operations such as the general formula [28]
Obtaining an optically active benzoic acid derivative wherein p is 0
Can be The optically active benzoic acid derivative obtained here [2
8] (where p is 0) is a substituent in the general formula [28]
A compound in which R 'is a hydroxyl group, which is
If necessary, the compound is converted to an acid halide by a known method to obtain a compound represented by the general formula
The compound wherein the substituent R 'in [28] is a halogen atom
Can be guided to (2) In the case where p is 1 In the general formula [28], the optically active repose in which p is 1
Perfumed acid derivatives are the optically active phenol derivatives mentioned above.
Optical activity used as a raw material in the production method (3) of [3]
Using a neutral alcohol compound [24] as a raw material,
It can be manufactured by a method.(In the above reaction formula, R ′, R^Two, N and * are the same as above.
B represents a taste, and B represents a protecting group for a hydroxyl group. Hereinafter, each step will be described in detail. Optically active acetopheno represented by the above general formula (29)
Are hydroxyl groups of the optically active alcohol compound [24].
It can be manufactured by protecting. This protecting group introduction reaction is carried out using an optically active alcohol compound.
[24] and a hydroxyl-protecting agent are reacted in the presence of a catalyst.
It is done by doing. Examples of the hydroxyl-protecting group include a methyl group and a benzyl group.
Alkyl or aralkyl such as
Group, methoxymethyl group, methoxyethoxymethyl group,
Toxiethyl group, tetrahydrofuryl group, tetrahydro
An alkoxyalkyl group such as a pranyl group, and further,
Trimethylsilyl group and t-butyldimethylsilyl group
Sometimes a silyl group is mentioned. The catalyst used in this reaction depends on the protecting agent used.
Although different, for example, the protecting group of the hydroxyl group is alkyl,
In the case of alkyl or some alkoxyalkyl groups,
Basic substances are preferably used. Such basic substances include, for example, sodium hydroxide
, Potassium hydroxide, sodium carbonate, potassium carbonate,
Sodium bicarbonate, potassium bicarbonate, sodium
Thiolate, sodium ethylate, sodium hydride,
Potassium hydride, n-butyllithium, sec-butyllithium
Inorganic or organic basic substances such as titanium. As the protective agent used in this case, specifically,
Methyl iodide, methyl bromide, benzyl chloride, benzyl
Rubromide, trityl chloride, chloromethyl methyl e
Or chloromethylmethoxyethoxyether.
I can do it. The amount of these protecting agents and catalysts used should be
It depends on the protective agent and cannot always be specified.
Usually, for the optically active alcohol compound [24] of the raw material
In the range of 1 to 5 equivalent times of the protecting agent and 1 to 4 equivalent times of the catalyst.
is there. This reaction is usually performed in the presence of a solvent, and the
Examples of the medium include ethyl ether and tetrahydrofuran.
Orchid, dioxane, acetone, methyl ethyl ketone,
Ruene, benzene, chlorobenzene, dichloromethane,
1,2-dichloroethane, chloroform, carbon tetrachloride, vinegar
Ethyl acid, dimethylformamide, dimethylsulfoxy
, Hexamethylphosphoryltriamide, acetonitrile
Ethers such as toluene, hexane and heptane, and halogenated carbonized
Inactive in reactions of hydrogen, esters, aprotic polar solvents, etc.
Or a mixture of neutral solvents.
Is not particularly limited. The reaction temperature depends on the protecting agent used, and
Although it can not be specified, usually in the range of -20 ℃ ~ 150 ℃
You. The reaction time is not particularly limited, and the optically active alcohol
The reaction can be terminated by disappearance of the urea compound [24].
it can. When the protecting group of the hydroxyl group is an alkoxyalkyl group
In this case, an acidic substance is preferably used as a catalyst.
Examples of such acidic substances include benzenesulfonic acid and p-toluene.
Ruenesulfonic acid, methanesulfonic acid, sulfuric acid, hydrogen sulfate
Potassium, hydrochloric acid, phosphoric acid, acetic acid, ammonium chloride, etc.
Inorganic or organic acidic substances. As the protective agent used in this case, specifically,
Dimethoxymethane, ethyl vinyl ether, dihydrofur
Orchid, dihydropyran and the like. The amount of these protecting agents and catalysts used should be
It depends on the protective agent and cannot always be specified.
Usually, for the optically active alcohol compound [24] of the raw material
Of the protecting agent in the range of 1 to 5 equivalents, and the catalyst in the range of 0.005 to 1 equivalent.
It is an enclosure. The reaction solvent, reaction temperature, and reaction time
Is the same as in the case of the protective group introduction reaction using as a catalyst. When the protecting group of the hydroxyl group is a silyl group, the catalyst may be a base.
Substances are preferably used. Such basic substances include, for example, sodium hydroxide
, Potassium hydroxide, sodium carbonate, potassium carbonate,
Sodium bicarbonate, potassium bicarbonate, sodium
Thiolate, sodium ethylate, sodium hydride,
Potassium hydride, n-butyllithium, sec-butyllithium
Tium, imidazole, pyridine, 4-dimethylamino
Inorganic or organic basic substances such as piuridine;
You. As the protective agent used in this case, specifically,
Trimethylsilyl chloride, trimethylsilyl bromi
And t-butyldimethylsilyl chloride.
You. The amount of these protecting agents and catalysts used should be
It depends on the protective agent and cannot always be specified.
Usually, for the optically active alcohol compound [24] of the raw material
In the range of 1 to 5 equivalent times of the protecting agent and 1 to 4 equivalent times of the catalyst.
is there. The reaction solvent, reaction temperature, and reaction time
Is the same as in the case of the protective group introduction reaction using as a catalyst. Optically active acetophenones obtained as described above
Removal from the reaction mixture of (29) includes, for example, extraction,
It is performed by adding ordinary post-processing operations such as separation and concentration.
Will be Optically active benzoic acids represented by the general formula [30]
Converts the optically active acetophenones (29) obtained above into water
It can be produced by oxidizing in the presence. This oxidation reaction is based on the aforementioned optically active benzoic acid derivative.
It can be carried out in the same manner as in the production method (1) of [28]. That is, optically active acetophenones [29]
The ability to convert the acetyl group to a carboxylic acid in the presence of
Oxidation with an oxidizing agent possesses an optically active
The benzoic acid [30] can be obtained. Removal of optically active benzoic acids [30] from reaction mixtures.
Discharge, for example, after filtration, acid precipitation, extraction, liquid separation, concentration, etc.
This is done by adding processing operations. The optically active hydroxy ammonium represented by the general formula (31)
The benzoic acids are water of the optically active benzoic acids [30] obtained above.
By deprotecting the protecting group of the acid group using a deprotecting agent,
Can be manufactured. This deprotection reaction is performed by protecting the hydroxyl group in the general formula [30].
The method differs depending on the type of protecting group B. The following describes the method
Will be described. A protecting group B for a hydroxyl group is an alkyl or aralkyl group;
In such a case, a Lewis acid is preferably used as the deprotecting agent.
Can be Such Lewis acids include, for example,
, Boron trifluoride, aluminum chloride, etc.
You. The amount of such a Lewis acid used usually depends on the optical activity of the raw material.
Benzoic acid [30] in the range of 1 to 5 equivalents
You. This reaction is usually carried out in a solvent, and
Benzene, toluene, hexane, heptane,
Chloromethane, 1,2-dichloroethane, chloroform, etc.
Solvents inert to hydrocarbons, halogenated hydrocarbons, etc.
Alone or as a mixture.
Is not particularly limited. The reaction temperature is usually in the range of -20C to 150C. The reaction time is not particularly limited, and the optically active benzo
The reaction can be terminated when the acids [30] disappear.
You. When the protecting group B for the hydroxyl group is an araalkyl group,
Is a benzyl or trityl group, hydrogenation catalyst
Deprotection by catalytic hydrogenation in the presence of
Can also be. In this catalytic hydrogenation reaction, transition as hydrogenation catalyst
A metal catalyst is preferably used, and as such a transition metal catalyst,
For example, platinum oxide such as platinum oxide, Pt-C, Pd-C,
Pd-BaSO_Four, Palladium such as palladium black, Rh-C, R
h-Al_TwoO_ThreeSuch as rhodium, ruthenium oxide, Ru-C, etc.
Ru-based or nickel-based contact such as Raney nickel
And palladium-based catalysts.
Particularly preferably used. The amount of these hydrogenation catalysts used depends on the optically active
Usually 0.01 to 100% by weight with respect to fragrances [30], preferred
The range is 0.1 to 50% by weight. Alcohols such as methanol and ethanol
Ethers such as coals, dioxane, tetrahydrofuran, etc.
, Aromatic hydrocarbons such as benzene, toluene, etc.
Aliphatic hydrocarbons such as sun and cyclohexane, ethyl acetate
Non-prototypes such as esters such as dimethylformamide
Polar solvents, fatty acids such as acetic acid or water
Independently applicable solvents alone or in mixtures are exemplified.
Their usage is not particularly limited. The hydrogen pressure during the reaction is usually in the range of 1 to 200 atm.
You. The reaction temperature is usually 0 ° C to 200 ° C, preferably 20 ° C to 1 ° C.
It is in the range of 80 ° C. The reaction time is not particularly limited, and the optically active benzo
Reaction with disappearance of acids [30] or termination of hydrogen absorption
Can be terminated. Next, if the protecting group B for the hydroxyl group is an alkoxyalkyl group,
The deprotection method for a silyl group will now be described. As a deprotecting agent in this case, an acid catalyst is preferably used.
Can be Such acid catalysts include benzenesulfonic acid,
p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, sulfuric acid
Potassium hydrogen oxychloride, hydrochloric acid, phosphoric acid, acetic acid, trifluorovinegar
Inorganic or organic acidic substances such as acids. Usually, the amount of such an acid catalyst used depends on the optical activity of the raw material.
Benzoic acids [30] in the range of 0.001 to 1 equivalent times
It is. In this reaction, if water or methanol is contained in the reaction system,
Requires the presence of a protic solvent such as ethanol.
You. Water, methanol or ethanol as the reaction solvent
Or a mixture of protic solvents such as
In addition, these protic solvents and the solvents shown below alone
Alternatively, a mixture can be used in combination. Dioxane, tetrahydrofuran, acetone, aceto
Nitrile, dimethylformamide, ethyl acetate, benze
, Toluene, hexane, heptane, dichloromethane,
1,2-dichloroethane, chloroform and the like. The reaction temperature is usually in the range of -20C to 150C. The reaction time is not particularly limited, and the optically active benzo
The reaction can be terminated when the acids [30] disappear.
You. Particularly, when the protecting group B for the hydroxyl group is a silyl group.
Can perform deprotection reaction in the presence of fluorine ions.
Wear. As a source of fluorine ions in this reaction,
Trabutylammonium fluoride, hydrogen fluoride,
Titanium tetrafluoroborate
The amount is usually based on the optically active benzoic acid [30] of the raw material.
In the range of 1 to 5 equivalent times. Dioxane, tetrahydrofura
, Acetone, acetonitrile, dimethylformamide
, Ethyl acetate, benzene, toluene, hexane, hept
Tan, dichloromethane, 1,2-dichloroethane, chloro
Ethers such as form, ketones, esters, aprotic
Does not react with polar solvents, hydrocarbons, halogenated hydrocarbons, etc.
Illustrative of active solvents, alone or in mixtures,
The amount used is not particularly limited. The reaction temperature is usually in the range of -20C to 150C. The reaction time is not particularly limited, and the optically active benzo
The reaction can be terminated when the acids [30] disappear.
You. Optically active hydroxybenzoic acid obtained as described above
The removal of acids [31] from the reaction mixture can be performed, for example, by extraction.
Add ordinary post-treatment operations such as extraction, liquid separation, and concentration.
Is performed. Optically active benzoic acid derivative which is the target compound [28]
(Where p is 1) is the optically active hydroxy ammonium obtained above.
The benzoic acids [31] are represented by the general formula [32] R^TwoCOR^Five [32] (where R^TwoRepresents the same meaning as described above, and R^FiveIs a halogen atom
Or R^TwoIndicates COO. ) To react with the acid halide or acid anhydride
And can be manufactured. Where the acid halide or acid anhydride [32]
Substitution R^TwoExamples thereof include those exemplified above. This reaction can be performed by applying a normal esterification method.
Reaction with a catalyst in the presence or absence of a solvent
Can be performed. As a catalyst used in this reaction, for example, dimethyl
Aminopyridine, tri-n-butylamine, pyridi
, Lysine, imidazole, sodium carbonate, sodium
Organic or inorganic salts such as mumethylate and potassium hydrogen carbonate
Basic substances. Also, toluenesulfonic acid, methanesulfonic acid, sulfuric acid
It is also possible to use organic or inorganic acids such as
Wear. The amount of catalyst used depends on the type of each raw material used and the catalyst used.
It depends on the combination of media, etc., and cannot always be specified.
No, for example, when using a basic substance as a catalyst
To the acid halide or acid anhydride [32]
Used at least one equivalent. The amount of acid halide or acid anhydride [32]
Optically active hydroxybenzoic acids [31]
It is usually in the range of 1 to 4 equivalents, preferably 1 to 2 equivalents.
You. If a solvent is used in this reaction,
For example, tetrahydrofuran, ethyl ether,
Seton, methyl ethyl ketone, toluene, benzene,
Lorbenzene, dichloromethane, dichloroethane, chloro
Roform, carbon tetrachloride, dimethylformamide, hexa
Aliphatic or aromatic hydrocarbons such as pyridine or pyridine,
For reactions of ethers, halogenated hydrocarbons, organic amines, etc.
Inert solvents may be used alone or as a mixture. The amount of such a solvent used is not particularly limited.
No. The reaction temperature is usually −30 ° C. to 100 ° C., preferably −2 ° C.
5 ° C to 80 ° C. The reaction time is not particularly limited.
With the disappearance of optically active hydroxybenzoic acids [31]
The reaction can be terminated. After completion of the reaction, usual post-treatments such as acid precipitation, extraction, and liquid separation
By adding operations such as the general formula [28]
Obtaining an optically active benzoic acid derivative wherein p is 1.
Can be The optically active benzoic acid derivative obtained here [2
8] (where p is 1) is a substituent in the general formula [28]
A compound in which R 'is a hydroxyl group, which is
If necessary, the compound is converted to an acid halide by a known method to obtain a compound represented by the general formula
The compound wherein the substituent R 'in [28] is a halogen atom
Can be guided to The trifluoromethyl obtained by the above-described production method
Specific as an optically active aromatic compound having a hydroxyl group [3]
Specifically, the following compounds are exemplified. (1) when X is -COO- 4-alkoxy (C3-20) benzoic acid 4-
[1-alkoxy (having 1 to 20 carbon atoms) -2,2,2-trif
Fluoroethyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[2-alkoxy (C1-20) -3,3,3-trif
Fluoropropyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[3-alkoxy (having 1 to 20 carbon atoms) -4,4,4-trif
Fluorobutyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[4-alkoxy (C1-20) -5,5,5-trif]
Fluoropentyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-trif
Fluorohexyl] phenyl, 4-alkoxy (3-20 carbon atoms) benzoic acid 4-
[6-alkoxy (C1-20) -7,7,7-trif]
Fluoroheptyl] phenyl, 4-alkyl (3-20 carbon atoms) benzoic acid 4- [1
-Alkoxy (having 1 to 20 carbon atoms) -2,2,2-trifluoro
4-ethyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [2
-Alkoxy (having 1 to 20 carbon atoms) -3,3,3-trifluoro
4-propyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [3
-Alkoxy (having 1 to 20 carbon atoms) -4,4,4-trifluoro
Robutyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [4
-Alkoxy (C1-20) -5,5,5-trifluoro
Lopentyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [5
-Alkoxy (having 1 to 20 carbon atoms) -6,6,6-trifluoro
Rohexyl] phenyl, 4-alkyl (3-20 carbon atoms) benzoic acid 4- [6
-Alkoxy (having 1 to 20 carbon atoms) -7,7,7-trifluoro
Roheptyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
Acid 4- [1-alkoxy (C1-20) -2,2,2
-Trifluoroethyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
Acid 4- [2-alkoxy (C1-20) -3,3,3
-Trifluoropropyl] phenyl, 4-alkoxy (C 3-20) carbonylbenzoic
Acid 4- [3-alkoxy (C1-20) -4,4,4
-Trifluorobutyl] phenyl, 4-alkoxy (C 3-20) carbonylbenzoic
Acid 4- [4-alkoxy (C1-20) -5,5,5
-Trifluoropentyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
Acid 4- [5-alkoxy (C1-20) -6,6,6
-Trifluorohexyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [6-alkoxy (C1-20) -7,7,7
-Trifluoroheptyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [1-alkoxy (C1-20) -2,
2,2-trifluoroethyl] phenyl, 4-alkyl (C 3-20) carbonyloxy ammonium
4- [2-alkoxy (C1-20) -3,
3,3-trifluoropropyl] phenyl, 4-alkyl (C 3-20) carbonyloxy ammonium
4-benzoic acid 4- [3-alkoxy (C1-20) -4,
4,4-trifluorobutyl] phenyl, 4-alkyl (C 3-20) carbonyloxy
4-benzoic acid 4- [4-alkoxy (C1-20) -5,
5,5-trifluoropentyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [5-alkoxy (C 1-20) -6,
6,6-trifluorohexyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4-benzoic acid 4- [6-alkoxy (C1-20) -7,
7,7-trifluoroheptyl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4-carboxylic acid 4- [1-alkoxy (C 1-20
) -2,2,2-trifluoroethyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [2-alkoxy (1-20 carbon atoms)
-3,3,3-trifluoropropyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [3-alkoxy (C 1-20
-4,4,4-trifluorobutyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [4-alkoxy (C 1-20
-5,5,5-trifluoropentyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [5-alkoxy (1-20 carbon atoms)
-6,6,6-trifluorohexyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [6-alkoxy (C 1-20
-7,7,7-Trifluoroheptyl] phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [1-alkoxy (C1-20)
-2,2,2-trifluoroethyl] phenyl, 4'-alkyl (C3-20) -4-biphenyl
Carboxylic acid 4- [2-alkoxy (C1-20)
-3,3,3-trifluoropropyl] phenyl, 4'-alkyl (C3-20) -4-biphenyl
Carboxylic acid 4- [3-alkoxy (C1-20)
-4,4,4-trifluorobutyl] phenyl, 4'-alkyl (C3-20) -4-biphenyl
Carboxylic acid 4- [4-alkoxy (C1-20)
-5,5,5-trifluoropentyl] phenyl, 4'-alkyl (3-20 carbon atoms) -4-biphenyl
Carboxylic acid 4- [5-alkoxy (C1-20)
-6,6,6-trifluorohexyl] phenyl, 4'-a
Alkyl (3-20 carbon atoms) -4-biphenylcarboxylic acid
 4- [6-alkoxy (C1-20) -7,7,7-
Trifluoroheptyl] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [1-alkoxy (carbon
-1) -2,2,2-trifluoroethyl] phenyl
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [2-alkoxy (carbon
-3,3,3-trifluoropropyl] pheny
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [3-alkoxy (carbon
-4,4,4-trifluorobutyl] phenyl
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [4-alkoxy (carbon
-5,5,5-trifluoropentyl] phenyl
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [5-alkoxy (carbon
-6,6,6-trifluorohexyl] pheny
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [6-alkoxy (carbon
-7,7,7-trifluoroheptyl] phenyl)
, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [1-alkoxy
(C 1-20) -2,2,2-trifluoroethyl]
Phenyl, 4'-alkyl (C3-C20) carbonyloxy
-4-biphenylcarboxylic acid 4- [2-alkoxy
(Having 1 to 20 carbon atoms) -3,3,3-trifluoropropyl]
Phenyl, 4'-alkyl (3 to 20 carbon atoms) carbonyloxy
4-biphenylcarboxylic acid 4- [3-alkoxy
-4,4,4-trifluorobutyl] (having 1 to 20 carbon atoms)
Phenyl, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [4-alkoxy
(Having 1 to 20 carbon atoms) -5,5,5-trifluoropentyl]
Phenyl, 4'-alkyl (3 to 20 carbon atoms) carbonyloxy
4-biphenylcarboxylic acid 4- [5-alkoxy
-6,6,6-trifluorohexyl (having 1 to 20 carbon atoms)]
Phenyl, 4'-alkyl (3 to 20 carbon atoms) carbonyloxy
4-biphenylcarboxylic acid 4- [6-alkoxy
-7,7,7-trifluoroheptyl (having 1 to 20 carbon atoms)]
Phenyl, 2- [4- [4- [1-alkoxy (C 1-20
) -2,2,2-trifluoroethyl] phenoxycarbo
Nyl] phenyl] -5-alkoxy (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [2-alkoxy (C 1-20)
) -3,3,3-Trifluoropropyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-trifluorobutyl] phenoxycarbo
Nyl] phenyl] -5-alkoxy (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [4-alkoxy (1 to 20 carbon atoms)
) -5,5,5-Trifluoropentyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [1-alkoxy (C 1-20)
) -2,2,2-trifluoroethyl] phenoxycarbo
Nyl] phenyl] -5-alkyl (C3-C20) pi
Limidine, 2- [4- [4- [2-alkoxy (1 to 20 carbon atoms)
) -3,3,3-Trifluoropropyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [3-alkoxy (1 to 20 carbon atoms)
-4,4,4-trifluorobutyl] phenoxycarbo
Nyl] phenyl] -5-alkyl (C3-C20) pi
Limidine, 2- [4- [4- [4-alkoxy (1 to 20 carbon atoms)
) -5,5,5-Trifluoropentyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [5-alkoxy (1 to 20 carbon atoms)
-6,6,6-Trifluorohexyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [6-alkoxy (1 to 20 carbon atoms)
-7,7,7-Trifluoroheptyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Pyrimidine, 2- [4- [4- [1-alkoxy (1 to 20 carbon atoms)
) -2,2,2-trifluoroethyl] phenoxycarbo
Nyl] phenyl] -5-alkoxy (having 3 to 20 carbon atoms)
Carbonylpyrimidine, 2- [4- [4- [2-alkoxy (1 to 20 carbon atoms)
) -3,3,3-Trifluoropropyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Carbonylpyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-trifluorobutyl] phenoxycarbo
Nyl] phenyl] -5-alkoxy (having 3 to 20 carbon atoms)
Carbonyl pyrimidine, 2- [4- [4- [4-alkoxy (1 to 20 carbon atoms)
) -5,5,5-Trifluoropentyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Carbonylpyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Carbonyl pyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenoxycal
Bonyl] phenyl] -5-alkoxy (3-20 carbon atoms)
Carbonyl pyrimidine, 2- [4- [4- [1-alkoxy (C 1-20)
) -2,2,2-trifluoroethyl] phenoxycarbo
Nyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Rubonyloxypyrimidine, 2- [4- [4- [2-alkoxy (C1-20
) -3,3,3-Trifluoropropyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-trifluorobutyl] phenoxycarbo
Nyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Rubonyloxypyrimidine, 2- [4- [4- [4-alkoxy (1 to 20 carbon atoms)
) -5,5,5-Trifluoropentyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenoxycal
Bonyl] phenyl] -5-alkyl (having 3 to 20 carbon atoms)
Carbonyloxypyrimidine, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[1-alkoxyalkoxy (C 2-20) -2,2,
2-trifluoroethyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[2-alkoxyalkoxy (C2-20) -3,3,
3-trifluoropropyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[3-alkoxyalkoxy (C2-20) -4,4,
4-trifluorobutyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[4-alkoxyalkoxy (C2-20) -5,5,
5-trifluoropentyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[5-alkoxyalkoxy (C2-20) -6,6,
6-trifluorohexyl] phenyl, 4-alkoxy (C3-20) benzoic acid 4-
[6-alkoxyalkoxy (C2-20) -7,7,
7-trifluoroheptyl] phenyl, 4-alkyl (3-20 carbon atoms) benzoic acid 4- [1
-Alkoxyalkoxy (having 2 to 20 carbon atoms) -2,2,2-
Trifluoroethyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [2
-Alkoxyalkoxy (having 2 to 20 carbon atoms) -3,3,3-
Trifluoropropyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [3
-Alkoxyalkoxy (C2-20) -4,4,4-
Trifluorobutyl] phenyl, 4-alkyl (3-20 carbon atoms) benzoic acid 4- [4
-Alkoxyalkoxy (C2-20) -5,5,5-
Trifluoropentyl] phenyl, 4-alkyl (3-20 carbon atoms) benzoic acid 4- [5
-Alkoxyalkoxy (having 2 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [6
-Alkoxyalkoxy (having 2 to 20 carbon atoms) -7,7,7-
Trifluoroheptyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
Acid 4- [1-alkoxyalkoxy (C 2-20
) -2,2,2-trifluoroethyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [2-alkoxyalkoxy (C 2-20
-3,3,3-trifluoropropyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [3-alkoxyalkoxy (C 2-20
-4,4,4-trifluorobutyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [4-alkoxyalkoxy (C 2-20
-5,5,5-Trifluoropentyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [5-alkoxyalkoxy (C 2-20
-6,6,6-trifluorohexyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
Acid 4- [6-alkoxyalkoxy (C 2-20
-7,7,7-trifluoroheptyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [1-alkoxyalkoxy (C2-C2)
20) -2,2,2-trifluoroethyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [2-alkoxyalkoxy benzoic acid (2 to 2 carbon atoms)
20) -3,3,3-trifluoropropyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [3-alkoxyalkoxy benzoic acid (2 to 2 carbon atoms)
20) -4,4,4-trifluorobutyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [4-alkoxyalkoxy benzoic acid (2 to 2 carbon atoms)
20) -5,5,5-trifluoropentyl] phenyl, 4-alkyl (C 3-20) carbonyloxy
4- [5-alkoxyalkoxy acid (2-carbon)
20) -6,6,6-trifluorohexyl] phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [6-alkoxyalkoxy benzoic acid (C2-C2)
20) -7,7,7-trifluoroheptyl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4-carboxylic acid 4- [1-alkoxyalkoxy (carbon
2) -2,2,2-trifluoroethyl] phenyl
4'-Alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] phenyi
4'-Alkoxy (C3-C20) -4-biphenyl
Carboxylic acid 4- [3-alkoxyalkoxy (carbon
-4,4,4-trifluorobutyl] pheny
4'-Alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] phenyi
4'-Alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] phenyi
4'-Alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [6-alkoxyalkoxy (carbon
-7,7,7-trifluoroheptyl] pheny
, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [1-alkoxyalkoxy (carbon number
2-20) -2,2,2-trifluoroethyl] phenyl, 4'-alkyl (3-20 carbon atoms) -4-biphenyl
Carboxylic acid 4- [2-alkoxyalkoxy (carbon number
2-20) -3,3,3-trifluoropropyl] phenyi
, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [3-alkoxyalkoxy (carbon number
2-20) -4,4,4-trifluorobutyl] phenyl, 4'-alkyl (3-20 carbon atoms) -4-biphenyl
Carboxylic acid 4- [4-alkoxyalkoxy (carbon number
2-20) -5,5,5-trifluoropentyl] phenyi
, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [5-alkoxyalkoxy (carbon number
2-20) -6,6,6-trifluorohexyl] phenyi
, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [6-alkoxyalkoxy (carbon number
2-20) -7,7,7-trifluoroheptyl] phenyi
4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [1-alkoxyalcohol
Xy (C2-20) -2,2,2-trifluoroethyl
Ru] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [2-alkoxyalcohol
Xy (2-20 carbon atoms) -3,3,3-trifluoropropy
Ru] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [3-alkoxyalcohol
Xy (2-20 carbon atoms) -4,4,4-trifluorobuty
Ru] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [4-alkoxyalcohol
Xy (2-20 carbon atoms) -5,5,5-trifluoropentene
Ru] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [5-alkoxyalcohol
Xy (2 to 20 carbon atoms) -6,6,6-trifluorohexy
Ru] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [6-alkoxy alcohol
Xy (C2-20) -7,7,7-trifluorohepti
L] phenyl, 4'-alkyl (C3-C20) carbonyloxy
-4-biphenylcarboxylic acid 4- [1-alkoxya
Lucoxy (having 1 to 20 carbon atoms) -2,2,2-trifluoroe
Tyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
-4-biphenylcarboxylic acid 4- [2-alkoxya
Lucoxy (2-20 carbon atoms) -3,3,3-trifluoroprop
Ropyl] phenyl, 4'-alkyl (3 to 20 carbon atoms) carbonyloxy
4-biphenylcarboxylic acid 4- [3-alkoxya
Lucoxy (C2-20) -4,4,4-trifluorobu
Tyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
-4-biphenylcarboxylic acid 4- [4-alkoxya
Lucoxy (having 2 to 20 carbon atoms) -5,5,5-trifluorope
Phenyl], 4'-alkyl (3-20 carbon atoms) carbonyloxy
-4-biphenylcarboxylic acid 4- [5-alkoxya
Lucoxy (2 to 20 carbon atoms) -6,6,6-trifluorohe
Xyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [6-alkoxya
Lucoxy (having 1 to 20 carbon atoms) -7,7,7-trifluoro
Butyl] phenyl, 2- [4- [4- [1-alkoxyalkoxy (carbon
2) -20,2,2-trifluoroethyl] phenoxy
[Cicarbonyl] phenyl] -5-alkoxy (C3
-20) pyrimidine, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
Pyrimidine, 2- [4- [4- [3-alkoxyalkoxy (carbon
-4,4,4-trifluorobutyl] of Formulas 2 to 20
[Cicarbonyl] phenyl] -5-alkoxy (C3
-20) pyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) pyrimidine, 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) pyrimidine, 2- [4- [4- [6-alkoxyalkoxy (carbon
2-7) -7,7,7-trifluoroheptyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) pyrimidine, 2- [4- [4- [1-alkoxyalkoxy (carbon
2) -20,2,2-trifluoroethyl] phenoxy
[Cicarbonyl] phenyl] -5-alkyl (having 3 to 3 carbon atoms)
20) pyrimidine, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) pyrimidine, 2- [4- [4- [3-alkoxyalkoxy (carbon
-4,4,4-trifluorobutyl] of Formulas 2 to 20
[Cicarbonyl] phenyl] -5-alkyl (having 3 to 3 carbon atoms)
Pyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) pyrimidine, 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) pyrimidine, 2- [4- [4- [6-alkoxyalkoxy (carbon
2-7) -7,7,7-trifluoroheptyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) pyrimidine, 2- [4- [4- [1-alkoxyalkoxy (carbon
2) -20,2,2-trifluoroethyl] phenoxy
[Cicarbonyl] phenyl] -5-alkoxy (C3
-20) carbonyl pyrimidine, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) carbonylpyrimidine, 2- [4- [4- [3-alkoxyalkoxy (carbon
-4,4,4-trifluorobutyl] of Formulas 2 to 20
[Cicarbonyl] phenyl] -5-alkoxy (C3
-20) carbonylpyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) carbonylpyrimidine, 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) carbonylpyrimidine, 2- [4- [4- [6-alkoxyalkoxy (carbon
2-7) -7,7,7-trifluoroheptyl] pheno
[Xycarbonyl] phenyl] -5-alkoxy (carbon number
3-20) carbonylpyrimidine, 2- [4- [4- [1-alkoxyalkoxy (carbon
2) -20,2,2-trifluoroethyl] phenoxy
[Cicarbonyl] phenyl] -5-alkyl (having 3 to 3 carbon atoms)
20) carbonyloxypyrimidine, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) carbonyloxypyrimidine, 2- [4- [4- [3-alkoxyalkoxy (carbon
-4,4,4-trifluorobutyl] of Formulas 2 to 20
[Cicarbonyl] phenyl] -5-alkyl (having 3 to 3 carbon atoms)
20) carbonyloxypyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) carbonyloxypyrimidine, 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) carbonyloxypyrimidine, 2- [4- [4- [6-alkoxyalkoxy (carbon
2-7) -7,7,7-trifluoroheptyl] pheno
Xycarbonyl] phenyl] -5-alkyl (C3
-20) carbonyloxypyrimidine, 4-alkoxy (3-20 carbon) benzoic acid 4-
[1-alkyl (C 1-20) carbonyloxy-
2,2,2-trifluoroethyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[2-alkyl (C 1-20) carbonyloxy-
3,3,3-trifluoropropyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[3-alkyl (C1-20) carbonyloxy-
4,4,4-trifluorobutyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[4-alkyl (1-20 carbon) carbonyloxy-
5,5,5-trifluoropentyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[5-alkyl (1-20 carbon) carbonyloxy-
6,6,6-trifluorohexyl] phenyl, 4-alkoxy (C3-20) benzoic acid 4-
[6-alkyl (C 1-20) carbonyloxy-
7,7,7-trifluoroheptyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [1
-Alkyl (C 1-20) carbonyloxy-2,2,
2-trifluoroethyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [2
-Alkyl (C 1-20) carbonyloxy-3,3,
3-trifluoropropyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [3
-Alkyl (C 1-20) carbonyloxy-4,4,
4-trifluorobutyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [4
-Alkyl (C 1-20) carbonyloxy-5,5,
5-trifluoropentyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [5
-Alkyl (C 1-20) carbonyloxy-6,6,
6-trifluorohexyl] phenyl, 4-alkyl (3 to 20 carbon atoms) benzoic acid 4- [6
-Alkyl (C 1-20) carbonyloxy-7,7,
7-trifluoroheptyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
4- [1-alkyl (C1-20) carbonyl] acid
Oxy-2,2,2-trifluoroethyl] phenyl, 4-alkoxy (C 3-20) carbonylbenzoic
4- [2-alkyl (C1-20) carbonyl] acid
Oxy-3,3,3-trifluoropropyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
4- [3-alkyl (C1-20) carbonyl] acid
Oxy-4,4,4-trifluorobutyl] phenyl, 4-alkoxy (C 3-20) carbonylbenzoic
4- [4-alkyl (C1-20) carbonyl] acid
Oxy-5,5,5-trifluoropentyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
4- [5-alkyl (C1-20) carbonyl] acid
Oxy-6,6,6-trifluorohexyl] phenyl, 4-alkoxy (C3-20) carbonylbenzoic
4- [6-alkyl (C1-20) carbonyl] acid
Oxy-7,7,7-trifluoroheptyl] phenyl, 4-alkyl (C 3-20) carbonyloxy
4- [1-alkyl (1-C20) carbocarboxylate
Nyloxy-2,2,2-trifluoroethyl] phenyl, 4-alkyl (C 3-20) carbonyloxy
4- [2-alkyl (1-C20) carbocarboxylate
Nyloxy-3,3,3-trifluoropropyl] phenyl
4-alkyl (3-20 carbon atoms) carbonyloxy ammonium
4- [3-alkyl (1-C20) carbocarboxylate
Nyloxy-4,4,4-trifluorobutyl] phenyl, 4-alkyl (C 3-20) carbonyloxy
4- [4-alkyl (1-C20) carbocarboxylate
Nyloxy-5,5,5-trifluoropentyl] phenyi
4-alkyl (3-20 carbon atoms) carbonyloxy ammonium
4- [5-alkyl carboxylate (1 to 20 carbon atoms) carboxy
Nyloxy-6,6,6-trifluorohexyl] phenyi
4-alkyl (3-20 carbon atoms) carbonyloxy ammonium
4- [6-alkyl (1-C20) carbocarboxylate
Nyloxy-7,7,7-trifluoroheptyl] phenyi
4'-Alkoxy (C3-C20) -4-biphenyl
4- [1-alkyl carboxylate (having 1 to 20 carbon atoms)
Carbonyloxy-2,2,2-trifluoroethyl]
Nyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-Carboxylic acid 4- [2-alkyl (having 1 to 20 carbon atoms)
Carbonyloxy-3,3,3-trifluoropropyl]
Phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4- [3-alkyl carboxylate (having 1 to 20 carbon atoms)
Carbonyloxy-4,4,4-trifluorobutyl]
Nyl, 4'-alkoxy (C3-C20) -4-biphenyl
4- [4-alkyl carboxylate (having 1 to 20 carbon atoms)
Carbonyloxy-5,5,5-trifluoropentyl] f
Phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4- [5-alkyl carboxylate (having 1 to 20 carbon atoms)
Carbonyloxy-6,6,6-trifluorohexyl] f
Phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4- [6-alkyl carboxylate (having 1 to 20 carbon atoms)
Carbonyloxy-7,7,7-trifluoroheptyl] f
Phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [1-alkyl (having 1 to 20 carbon atoms)
Rubonyloxy-2,2,2-trifluoroethyl] phenyl
, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [2-alkyl (having 1 to 20 carbon atoms)
Rubonyloxy-3,3,3-trifluoropropyl] fe
Nyl, 4'-alkyl (C3-C20) -4-biphenyl
4- [3-alkyl carboxylic acid (having 1 to 20 carbon atoms)
Rubonyloxy-4,4,4-trifluorobutyl] phenyl
, 4'-alkyl (C3-C20) -4-biphenyl
4- [4-alkyl carboxylic acid (having 1 to 20 carbon atoms)
Rubonyloxy-5,5,5-trifluoropentyl] fe
Nyl, 4'-alkyl (C3-C20) -4-biphenyl
4- [5-alkyl carboxylic acid (having 1 to 20 carbon atoms)
Rubonyloxy-6,6,6-trifluorohexyl] fe
Nyl, 4'-alkyl (C3-C20) -4-biphenyl
4- [6-alkyl carboxylic acid (having 1 to 20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] fe
Nyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [1-alkyl (carbon number
1-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [2-alkyl (carbon number
1-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [3-alkyl (carbon number
1-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [4-alkyl (carbon number
1-20) carbonyloxy-5,5,5-trifluorope
Nthyl] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [5-alkyl (carbon number
1-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenyl, 4'-alkoxy (C3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [6-alkyl (carbon number
1-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
4-biphenylcarboxylic acid 4- [1-alkyl (charcoal
Carbonyloxy-2,2,2-trifluoro (prime 1-20)
[Roethyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
4-biphenylcarboxylic acid 4- [2-alkyl (charcoal
Carbonyloxy-3,3,3-trifluoro (prime 1-20)
L-propyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [3-alkyl (charcoal
Carbonyloxy-4,4,4-trifluoro (prime 1-20)
Butyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [4-alkyl (charcoal
Carbonyloxy-5,5,5-trifluoro (prime 1-20)
Lopentyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
4-biphenylcarboxylic acid 4- [5-alkyl (charcoal
Carbonyloxy-6,6,6-trifluoro (prime 1-20)
Rohexyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
4-biphenylcarboxylic acid 4- [6-alkyl (charcoal
Carbonyloxy-7,7,7-trifluoro (prime 1-20)
Roheptyl] phenyl, 2- [4- [4- [1-alkyl (C1-20)]
Carbonyloxy-2,2,2-trifluoroethyl]
Nonoxycarbonyl] phenyl] -5-alkoxy (carbon
Pyrimidine having the number of 3 to 20; 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-3,3,3-trifluoropropyl]
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20; 2- [4- [4- [3-alkyl (having a carbon number of 1 to 20)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nonoxycarbonyl] phenyl] -5-alkoxy (carbon
Pyrimidine having the number of 3 to 20), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20; 2- [4- [4- [5-alkyl (having a carbon number of 1 to 20)]
Carbonyloxy-6,6,6-trifluorohexyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20), 2- [4- [4- [6-alkyl (having a carbon number of 1 to 20)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20; 2- [4- [4- [1-alkyl (having a carbon number of 1 to 20)]
Carbonyloxy-2,2,2-trifluoroethyl]
Nonoxycarbonyl] phenyl] -5-alkyl (carbon number
Pyrimidine, 3- [4- [4- [2-alkyl (C1-20)]
Carbonyloxy-3,3,3-trifluoropropyl]
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20; 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nonoxycarbonyl] phenyl] -5-alkyl (carbon number
Pyrimidine, 2- [4- [4- [4-alkyl (C1-20)]
Carbonyloxy-5,5,5-trifluoropentyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Pyrimidines having 2 to 20 carbon atoms; 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20; 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20; 2- [4- [4- [1-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-2,2,2-trifluoroethyl]
Nonoxycarbonyl] phenyl] -5-alkoxy (carbon
2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms) carbonylpyrimidine;
Carbonyloxy-3,3,3-trifluoropropyl]
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (prime 3-20), 2- [4- [4- [3-alkyl (C1-20)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nonoxycarbonyl] phenyl] -5-alkoxy (carbon
Carbonylpyrimidine (having the number of 3 to 20), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (prime 3-20), 2- [4- [4- [5-alkyl (C1-20)]
Carbonyloxy-6,6,6-trifluorohexyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (prime 3-20), 2- [4- [4- [6-alkyl (C1-20)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
[Enoxycarbonyl] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (prime number 3-20), 2- [4- [4- [1-alkyl (C1-20))
Carbonyloxy-2,2,2-trifluoroethyl]
Nonoxycarbonyl] phenyl] -5-alkyl (carbon number
Carbonyloxypyrimidine (of 3 to 20), 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-3,3,3-trifluoropropyl]
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine (having a number of 3 to 20), 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nonoxycarbonyl] phenyl] -5-alkyl (carbon number
Carbonyloxypyrimidine (of 3 to 20), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine (having the number 3 to 20), 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine (having a number of 3 to 20), 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
[Enoxycarbonyl] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[1-Alkoxyalkyl (C2-C20) carbonyl
4-oxy-2,2,2-trifluoroethyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[2-alkoxyalkyl (C2-C20) carbonyl
4-oxy-3,3,3-trifluoropropyl] phenyl, 4-alkoxy (having 3 to 20 carbon atoms) benzoic acid 4-
[3-alkoxyalkyl (C2-C20) carbonyl
4-oxy-4,4,4-trifluorobutyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) benzoic acid 4-
[4-Alkoxyalkyl (C2-C20) carbonyl
4-oxy-5,5,5-trifluoropentyl] phenyl, 4-alkoxy (3-20 carbon atoms) benzoic acid 4-
[5-Alkoxyalkyl (C2-C20) carbonyl
4-oxy-6,6,6-trifluorohexyl] phenyl, 4-alkoxy (3-20 carbon atoms) benzoic acid 4-
[6-alkoxyalkyl (C2-C20) carbonyl
4-oxy (7,7,7-trifluoroheptyl) phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [1
-Alkoxyalkyl (C 2-20) carbonyl
Xy-2,2,2-trifluoroethyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [2
-Alkoxyalkyl (C 2-20) carbonyl
Xy-3,3,3-trifluoropropyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [3
-Alkoxyalkyl (C 2-20) carbonyl
Xy-4,4,4-trifluorobutyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [4
-Alkoxyalkyl (C 2-20) carbonyl
Xy-5,5,5-trifluoropentyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [5
-Alkoxyalkyl (C 2-20) carbonyl
Xy-6,6,6-trifluorohexyl] phenyl, 4-alkyl (3-20 carbon) benzoic acid 4- [6
-Alkoxyalkyl (C 2-20) carbonyl
Xy-7,7,7-trifluoroheptyl] phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonylbenzoic
Acid 4- [1-alkoxyalkyl (C2-20)
Carbonyloxy-2,2,2-trifluoroethyl]
Nyl, 4-alkoxy (C3-C20) carbonyl benzoic
Acid 4- [2-alkoxyalkyl (C2-20)
Carbonyloxy-3,3,3-trifluoropropyl]
Phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonyl benzoate
4- [3-Alkoxyalkyl acid (C2-20)
Carbonyloxy-4,4,4-trifluorobutyl]
Nyl, 4-alkoxy (C3-C20) carbonyl benzoic
4- [4-Alkoxyalkyl acid (C2-20)
Carbonyloxy-5,5,5-trifluoropentyl] f
Phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonyl benzoate
4- [5-Alkoxyalkyl acid (C2-20)
Carbonyloxy-6,6,6-trifluorohexyl] f
Phenyl, 4-alkoxy (3 to 20 carbon atoms) carbonyl benzoate
Acid 4- [6-alkoxyalkyl (C2-20)
Carbonyloxy-7,7,7-trifluoroheptyl] f
Phenyl, 4-alkyl (3-20 carbon) carbonyloxy ammonium
4- [1-alkoxyalkyl benzoate (2-20 carbon atoms)
Carbonyloxy-2,2,2-trifluoroethyl]
Phenyl, 4-alkyl (3 to 20 carbon atoms) carbonyloxy ammonium
4- [2-alkoxyalkyl benzoic acid (2-20 carbon atoms)
) Carbonyloxy-3,3,3-trifluoropropyl
Phenyl], 4-alkyl (3 to 20 carbon atoms) carbonyloxy ammonium
4- [3-alkoxyalkyl benzoate (2-20 carbon atoms)
Carbonyloxy-4,4,4-trifluorobutyl]
Phenyl, 4-alkyl (3 to 20 carbon atoms) carbonyloxy ammonium
4- [4-alkoxyalkyl benzoate (2 to 20 carbon atoms)
Carbonyloxy-5,5,5-trifluoropentene
Phenyl], 4-alkyl (3 to 20 carbon atoms) carbonyloxy ammonium
4- [5-alkoxyalkyl benzoate (2-20 carbon atoms)
) Carbonyloxy-6,6,6-trifluorohexyl
Phenyl], 4-alkyl (3 to 20 carbon atoms) carbonyloxy ammonium
4- [6-alkoxyalkyl benzoate (C 2-20
Carbonyloxy-7,7,7-trifluorohepti
L] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [1-alkoxyalkyl (carbon number
2-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4-carboxylic acid 4- [2-alkoxyalkyl (carbon number
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenyl, 4'-alkoxy (C3-C20) -4-biphenyl
4-carboxylic acid 4- [3-alkoxyalkyl (carbon number
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4- [4-alkoxyalkyl carboxylate (carbon number
2-20) carbonyloxy-5,5,5-trifluorope
Nthyl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4-carboxylic acid 4- [5-alkoxyalkyl (carbon number
2-20) carbonyloxy-6,6,6-trifluoro
Chityl] phenyl, 4'-alkoxy (having 3 to 20 carbon atoms) -4-biphenyl
4-carboxylic acid 4- [6-alkoxyalkyl (carbon number
2-20) carbonyloxy-7,7,7-trifluoro
Butyl] phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [1-alkoxyalkyl (C 2
~ 20) carbonyloxy-2,2,2-trifluoroethyl
L] phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [2-alkoxyalkyl (C 2
-20) carbonyloxy-3,3,3-trifluoropro
Pyl] phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [3-alkoxyalkyl (C 2
~ 20) carbonyloxy-4,4,4-trifluorobutyi
L] phenyl, 4'-alkyl (C3-C20) -4-biphenyl
Carboxylic acid 4- [4-alkoxyalkyl (C 2
-20) carbonyloxy-5,5,5-trifluoropen
Tyl] phenyl, 4'-alkyl (C3-20) -4-biphenyl
Carboxylic acid 4- [5-alkoxyalkyl (C 2
~ 20) carbonyloxy-6,6,6-trifluorohex
Tyl] phenyl, 4'-alkyl (C3-20) -4-biphenyl
Carboxylic acid 4- [6-alkoxyalkyl (C 2
~ 20) carbonyloxy-7,7,7-trifluorohep
Tyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [1-alkoxyalkyl
(C2-20) carbonyloxy-2,2,2-tri
Fluoroethyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [2-alkoxyalkyl
(C1-20) carbonyloxy-3,3,3-tri
Fluoropropyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [3-alkoxyalkyl
(C 1-20) carbonyloxy-4,4,4-tri
Fluorobutyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [4-alkoxyalkyl
(C2-20) carbonyloxy-5,5,5-tri
Fluoropentyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [5-alkoxyalkyl
(C2-C20) carbonyloxy-6,6,6-tri
Fluorohexyl] phenyl, 4′-alkoxy (C 3-20) carbonyl-4
-Biphenylcarboxylic acid 4- [6-alkoxyalkyl
(C2-20) carbonyloxy-7,7,7-tri
Fluoroheptyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
-4-biphenylcarboxylic acid 4- [1-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-2,2,2-
Trifluoroethyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
-4-biphenylcarboxylic acid 4- [2-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-3,3,3-
Trifluoropropyl] phenyl, 4'-alkyl (3 to 20 carbon atoms) carbonyloxy
4-biphenylcarboxylic acid 4- [3-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-4,4,4-
Trifluorobutyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
-4-biphenylcarboxylic acid 4- [4-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-5,5,5-
Trifluoropentyl] phenyl, 4'-alkyl (C3-C20) carbonyloxy
-4-biphenylcarboxylic acid 4- [5-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-6,6,6-
Trifluorohexyl] phenyl, 4'-alkyl (C3-20) carbonyloxy
4-biphenylcarboxylic acid 4- [6-alkoxya
Alkyl (2 to 20 carbon atoms) carbonyloxy-7,7,7-
Trifluoroheptyl] phenyl, 2- [4- [4- [1-alkoxyalkyl (carbon number
2-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenoxycarbonyl] phenyl] -5-alco
Xy (3-20 carbon atoms) pyrimidine, 2- [4- [4- [2-alkoxyalkyl (carbon number)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenoxycarbonyl] phenyl] -5-al
Coxy (3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [3-alkoxyalkyl (carbon number)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenoxycarbonyl] phenyl] -5-alco
Xy (C3-C20) pyrimidine, 2- [4- [4- [4-alkoxyalkyl (carbon number)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenoxycarbonyl] phenyl] -5-al
Coxy (3-20 carbon atoms) pyrimidine, 2- [4- [4- [5-alkoxyalkyl (carbon number)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenoxycarbonyl] phenyl] -5-al
Coxy (3-20 carbon atoms) pyrimidine, 2- [4- [4- [6-alkoxyalkyl (carbon number)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenoxycarbonyl] phenyl] -5-al
Coxy pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [1-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenoxycarbonyl] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [2-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenoxycarbonyl] phenyl] -5-al
Pyrididine (having 3 to 20 carbon atoms), 2- [4- [4- [3-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenoxycarbonyl] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [4-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenoxycarbonyl] phenyl] -5-al
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [5-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenoxycarbonyl] phenyl] -5-al
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [6-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenoxycarbonyl] phenyl] -5-al
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [1-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenoxycarbonyl] phenyl] -5-alco
Xy (having 3 to 20 carbon atoms) carbonylpyrimidine, 2- [4- [4- [2-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenoxycarbonyl] phenyl] -5-al
Coxy (having 3 to 20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [3-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenoxycarbonyl] phenyl] -5-alco
Xy (having 3 to 20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [4-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenoxycarbonyl] phenyl] -5-al
Coxy (having 3 to 20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [5-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenoxycarbonyl] phenyl] -5-al
Coxy (3-20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [6-alkoxyalkyl (carbon number)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenoxycarbonyl] phenyl] -5-al
Coxy (having 3 to 20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [1-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-2,2,2-trifluoroe
Tyl] phenoxycarbonyl] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [2-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenoxycarbonyl] phenyl] -5-al
Carbonyl (3-20 carbon atoms) carbonyloxypyrimidine, 2- [4- [4- [3-alkoxyalkyl (carbon number
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenoxycarbonyl] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [4-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenoxycarbonyl] phenyl] -5-al
Carbonyl (3-20 carbon atoms) carbonyloxypyrimidine, 2- [4- [4- [5-alkoxyalkyl (carbon number
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenoxycarbonyl] phenyl] -5-al
Carbonyl (3-20 carbon atoms) carbonyloxypyrimidine, 2- [4- [4- [6-alkoxyalkyl (carbon number)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenoxycarbonyl] phenyl] -5-al
Killed (C3-C20) carbonyloxypyrimidine
etc. (2) when X is -OCO- 4- [2-alkoxy (C1-20) -3,3,3-
Trifluoropropyl] 4-alkoxybenzoate (charcoal
Phenyl, 4- [3-alkoxy (1-20 carbon atoms) -4,4,4-
Trifluorobutyl] 4-alkoxybenzoate (carbon
Phenyl, 4- [4-alkoxy (having 1 to 20 carbon atoms) -5,5,5-
Trifluoropentyl] benzoic acid 4-alkoxy (charcoal
Phenyl, 4- [5-alkoxy (1-20 carbon atoms) -6,6,6-
Trifluorohexyl] 4-alkoxybenzoate (charcoal
Phenyl, 4- [6-alkoxy (1-20 carbon atoms) -7,7,7-)
Trifluoroheptyl] 4-alkoxybenzoate (charcoal
Phenyl, 4- [2-alkoxy (1-20 carbon atoms) -3,3,3-
Trifluoropropyl] 4-alkyl benzoate (carbon
Phenyl, 4- [3-alkoxy (1-20 carbon atoms) -4,4,4-
Trifluorobutyl] 4-alkyl benzoate (carbon number
Phenyl, 4- [4-alkoxy (1-20 carbons) -5,5,5-
Trifluoropentyl] 4-alkyl benzoate (carbon
Phenyl, 4- [5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] 4-alkyl benzoate (carbon
Phenyl, 4- [6-alkoxy (1-20 carbon atoms) -7,7,7-
Trifluoroheptyl] 4-alkyl benzoate (carbon
Phenyl, 4- [2-alkoxy (having 1 to 20 carbon atoms) -3,3,3-
Trifluoropropyl] 4-alkoxybenzoate (charcoal
Carbonylphenyl having a prime number of 3 to 20; 4- [3-alkoxy (having a carbon number of 1 to 20) -4,4,4-
Trifluorobutyl] 4-alkoxybenzoate (carbon
Carbonylphenyl having 4 to 20 carbon atoms, 4- [4-alkoxy (having 1 to 20 carbon atoms) -5,5,5-
Trifluoropentyl] benzoic acid 4-alkoxy (charcoal
Carbonylphenyl having a prime number of 3 to 20), 4- [5-alkoxy (having a carbon number of 1 to 20) -6,6,6-
Trifluorohexyl] 4-alkoxybenzoate (charcoal
Carbonylphenyl having a prime number of 3 to 20, 4- [6-alkoxy (having a carbon number of 1 to 20) -7,7,7-
Trifluoroheptyl] 4-alkoxybenzoate (charcoal
Carbonylphenyl having a prime number of 3 to 20; 4- [2-alkoxy (having a carbon number of 1 to 20) -3,3,3-
Trifluoropropyl] 4-alkyl benzoate (carbon
Carbonyloxyphenyl (of numbers 3 to 20), 4- [3-alkoxy (of 1 to 20 carbons) -4,4,4-
Trifluorobutyl] 4-alkyl benzoate (carbon number
3-20) carbonyloxyphenyl, 4- [4-alkoxy (1-20 carbon) -5,5,5-
Trifluoropentyl] 4-alkyl benzoate (carbon
Carbonyloxyphenyl having 4 to 20 carbon atoms, 4- [5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] 4-alkyl benzoate (carbon
Carbonyloxyphenyl having 4 to 20 carbon atoms, 4- [6-alkoxy (1 to 20 carbon atoms) -7,7,7-
Trifluoroheptyl] 4-alkyl benzoate (carbon
Carbonyloxyphenyl having 4 to 20 carbon atoms, 4- [2-alkoxy (1 to 20 carbon atoms) -3,3,3-
Trifluoropropyl] benzoic acid 4'-alkoxy
4-biphenylyl (having 3 to 20 carbon atoms), 4- [3-alkoxy (having 1 to 20 carbon atoms) -4,4,4-
Trifluorobutyl] benzoic acid 4'-alkoxy (charcoal
4-biphenylyl having a prime number of 3 to 20), 4- [4-alkoxy (having 1 to 20 carbon atoms) -5,5,5-
Trifluoropentyl] benzoic acid 4'-alkoxy
4-biphenylyl (having 3 to 20 carbon atoms), 4- [5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] benzoic acid 4'-alkoxy
4-biphenylyl (having 3 to 20 carbon atoms), 4- [6-alkoxy (having 1 to 20 carbon atoms) -7,7,7-
Trifluoroheptyl] benzoic acid 4'-alkoxy
4-biphenylyl (having 3 to 20 carbon atoms), 4- [2-alkoxy (having 1 to 20 carbon atoms) -3,3,3-
Trifluoropropyl] 4'-alkyl benzoate (charcoal
4-biphenylyl having a prime number of 3 to 20), 4- [3-alkoxy (having a carbon number of 1 to 20) -4,4,4-
Trifluorobutyl] 4'-alkyl benzoate (carbon
4-biphenylyl having the number of 3 to 20), 4- [4-alkoxy (having 1 to 20 carbon atoms) -5,5,5-
Trifluoropentyl] 4'-alkyl benzoate (charcoal
4-biphenylyl having a prime number of 3 to 20), 4- [5-alkoxy (having a carbon number of 1 to 20) -6,6,6-
Trifluorohexyl] 4'-alkyl benzoate (charcoal
4-biphenylyl having a prime number of 3 to 20, 4- [6-alkoxy (having a carbon number of 1 to 20) -7,7,7-
Trifluoroheptyl] 4'-alkyl benzoate (charcoal
4-biphenylyl having a prime number of 3 to 20, 4- [2-alkoxy (having a carbon number of 1 to 20) -3,3,3-
Trifluoropropyl] benzoic acid 4'-alkoxy
Carbonyl-4-biphenylyl (having 3 to 20 carbon atoms), 4- [3-alkoxy (having 1 to 20 carbon atoms) -4,4,4-
Trifluorobutyl] benzoic acid 4'-alkoxy (charcoal
Carbonyl-4-biphenylyl having a prime number of 3 to 20, 4- [4-alkoxy (having 1 to 20 carbon atoms) -5,5,5-
Trifluoropentyl] benzoic acid 4'-alkoxy
Carbonyl-4-biphenylyl (having 3 to 20 carbon atoms), 4- [5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] benzoic acid 4'-alkoxy
Carbonyl-4-biphenylyl (having 3 to 20 carbon atoms), 4- [6-alkoxy (having 1 to 20 carbon atoms) -7,7,7-
Trifluoroheptyl] benzoic acid 4'-alkoxy
Carbonyl-4-biphenylyl (having 3 to 20 carbon atoms), 4- [2-alkoxy (having 1 to 20 carbon atoms) -3,3,3-
Trifluoropropyl] 4'-alkyl benzoate (charcoal
Carbonyloxy-4-biphenylyl having a prime number of 3 to 20, 4- [3-alkoxy (having 1 to 20 carbon atoms) -4,4,4-
Trifluorobutyl] 4'-alkyl benzoate (carbon
Carbonyloxy-4-biphenylyl of the number 3-20), 4- [4-alkoxy (1-20 carbons) -5,5,5-
Trifluoropentyl] 4'-alkyl benzoate (charcoal
Carbonyloxy-4-biphenylyl having a prime number of 3 to 20, 4- [5-alkoxy (having 1 to 20 carbon atoms) -6,6,6-
Trifluorohexyl] 4'-alkyl benzoate (charcoal
Carbonyloxy-4-biphenylyl having a prime number of 3 to 20, 4- [6-alkoxy (1 to 20 carbon atoms) -7,7,7-
Trifluoroheptyl] 4'-alkyl benzoate (charcoal
Carbonyloxy-4-biphenylyl (having a prime number of 3 to 20), 2- [4- [4- [2-alkoxy (having a carbon number of 1 to 20)
) -3,3,3-Trifluoropropyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
Pyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-Trifluorobutyl] phenylcarbonate
[Loxy] phenyl] -5-alkoxy (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [4-alkoxy (C 1-20)
) -5,5,5-trifluoropentyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
Pyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
Pyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
Pyrimidine, 2- [4- [4- [2-alkoxy (C 1-20)
) -3,3,3-Trifluoropropyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-Trifluorobutyl] phenylcarbonate
[Roxy] phenyl] -5-alkyl (C3-20
Pyrimidine, 2- [4- [4- [4-alkoxy (C 1-20)
) -5,5,5-trifluoropentyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Pyrimidine, 2- [4- [4- [2-alkoxy (C 1-20)
) -3,3,3-Trifluoropropyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
20) carbonyl pyrimidine, 2- [4- [4- [3-alkoxy (C 1-20)
-4,4,4-Trifluorobutyl] phenylcarbonate
[Loxy] phenyl] -5-alkoxy (3-20 carbon atoms)
Carbonylpyrimidine, 2- [4- [4- [4-alkoxy (C1-20)
) -5,5,5-trifluoropentyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
20) carbonylpyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
20) carbonylpyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenylcarbo
Nyloxy] phenyl] -5-alkoxy (having 3 to 5 carbon atoms)
20) carbonylpyrimidine, 2- [4- [4- [2-alkoxy (C1-20)
) -3,3,3-Trifluoropropyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [3-alkoxy (C1-20)
-4,4,4-Trifluorobutyl] phenylcarbonate
[Roxy] phenyl] -5-alkyl (C3-20
Carbonyloxypyrimidine, 2- [4- [4- [4-alkoxy (C1-20)
) -5,5,5-trifluoropentyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [5-alkoxy (C 1-20)
-6,6,6-Trifluorohexyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Carbonyloxypyrimidine, 2- [4- [4- [6-alkoxy (C 1-20)
-7,7,7-Trifluoroheptyl] phenylcarbo
Niloxy] phenyl] -5-alkyl (3-20 carbon atoms)
Carbonyloxypyrimidine), 4- [2-alkoxyalkoxy (C2-20)
-3,3,3-trifluoropropyl] benzoic acid 4-al
Coxy (3 to 20 carbon atoms) phenyl, 4- [3-alkoxyalkoxy (2 to 20 carbon atoms)
-4,4,4-trifluorobutyl] benzoic acid 4-alco
Xy (3 to 20 carbon atoms) phenyl, 4- [4-alkoxyalkoxy (2 to 20 carbon atoms)
-5,5,5-trifluoropentyl] benzoic acid 4-al
Coxy (having 3 to 20 carbon atoms) phenyl, 4- [5-alkoxyalkoxy (having 2 to 20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4-al
Coxy (having 3 to 20 carbon atoms) phenyl, 4- [6-alkoxyalkoxy (having 2 to 20 carbon atoms)
-7,7,7-trifluoroheptyl] benzoic acid 4-al
Coxy (3-20 carbon atoms) phenyl, 4- [2-alkoxyalkoxy (2-20 carbon atoms)
-3,3,3-trifluoropropyl] benzoic acid 4-al
Killed (C3-C20) phenyl, 4- [3-alkoxyalkoxy (C2-C20)
-4,4,4-trifluorobutyl] benzoic acid 4-alkyl
Phenyl (having 3 to 20 carbon atoms) phenyl, 4- [4-alkoxyalkoxy (having 2 to 20 carbon atoms)
-5,5,5-trifluoropentyl] benzoic acid 4-al
Killed (C3-C20) phenyl, 4- [5-alkoxyalkoxy (C2-C20)
-6,6,6-trifluorohexyl] benzoic acid 4-al
Killed (C3-C20) phenyl, 4- [6-alkoxyalkoxy (C2-C20)
-7,7,7-trifluoroheptyl] benzoic acid 4-al
Killed (C3-C20) phenyl, 4- [2-alkoxyalkoxy (C2-C20)
-3,3,3-trifluoropropyl] benzoic acid 4-al
Coxy (having 3 to 20 carbon atoms) carbonylphenyl, 4- [3-alkoxyalkoxy (having 2 to 20 carbon atoms)
-4,4,4-trifluorobutyl] benzoic acid 4-alco
Xy (3-20 carbon atoms) carbonylphenyl, 4- [4-alkoxyalkoxy (2-20 carbon atoms)
-5,5,5-trifluoropentyl] benzoic acid 4-al
Coxy (having 3 to 20 carbon atoms) carbonylphenyl, 4- [5-alkoxyalkoxy (having 2 to 20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4-al
Coxy (having 3 to 20 carbon atoms) carbonylphenyl, 4- [6-alkoxyalkoxy (having 2 to 20 carbon atoms)
-7,7,7-trifluoroheptyl] benzoic acid 4-al
Coxy (3-20 carbon atoms) carbonylphenyl, 4- [2-alkoxyalkoxy (2-20 carbon atoms)
-3,3,3-trifluoropropyl] benzoic acid 4-al
Carbonyl (3-20 carbon atoms) carbonyloxyphenyl, 4- [3-alkoxyalkoxy (2-20 carbon atoms)
-4,4,4-trifluorobutyl] benzoic acid 4-alkyl
Carbonyloxyphenyl (having 3 to 20 carbon atoms), 4- [4-alkoxyalkoxy (having 2 to 20 carbon atoms)
-5,5,5-trifluoropentyl] benzoic acid 4-al
Killed carbonyloxyphenyl (having 3 to 20 carbon atoms), 4- [5-alkoxyalkoxy (having 2 to 20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4-al
Carbonyl (3-20 carbon atoms) carbonyloxyphenyl, 4- [6-alkoxyalkoxy (2-20 carbon atoms)
-7,7,7-trifluoroheptyl] benzoic acid 4-al
Carbonyl (3-20 carbon atoms) carbonyloxyphenyl, 4- [2-alkoxyalkoxy (2-20 carbon atoms)
-3,3,3-trifluoropropyl] benzoic acid 4'-a
Lucoxy (having 3 to 20 carbon atoms) -4-biphenylyl, 4- [3-alkoxyalkoxy (having 2 to 20 carbon atoms)
-4,4,4-trifluorobutyl] benzoic acid 4'-al
Coxy (C3-C20) -4-biphenylyl, 4- [4-alkoxyalkoxy (C2-C20)
−5,5,5-trifluoropentyl] benzoic acid 4′-a
Lucoxy (having 3 to 20 carbon atoms) -4-biphenylyl, 4- [5-alkoxyalkoxy (having 2 to 20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4'-a
Lucoxy (having 3 to 20 carbon atoms) -4-biphenylyl, 4- [6-alkoxyalkoxy (having 2 to 20 carbon atoms)
-7,7,7-trifluoroheptyl] benzoic acid 4'-a
Lucoxy (having 3 to 20 carbon atoms) -4-biphenylyl, 4- [2-alkoxyalkoxy (having 2 to 20 carbon atoms)
-3,3,3-trifluoropropyl] benzoic acid 4'-a
Alkyl (3-20 carbon atoms) -4-biphenylyl, 4- [3-alkoxyalkoxy (2-20 carbon atoms)
-4,4,4-trifluorobutyl] benzoic acid 4'-al
Kill (3-20 carbon atoms) -4-biphenylyl, 4- [4-alkoxyalkoxy (2-20 carbon atoms)
−5,5,5-trifluoropentyl] benzoic acid 4′-a
Alkyl (3-20 carbon atoms) -4-biphenylyl, 4- [5-alkoxyalkoxy (2-20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4'-a
Alkyl (3-20 carbon atoms) -4-biphenylyl, 4- [6-alkoxyalkoxy (2-20 carbon atoms)
-7,7,7-trifluoroheptyl] benzoic acid 4'-a
Alkyl (3-20 carbon atoms) -4-biphenylyl, 4- [2-alkoxyalkoxy (2-20 carbon atoms)
-3,3,3-trifluoropropyl] benzoic acid 4'-a
Lucoxy (3-20 carbon atoms) carbonyl-4-biphenyl
Ryl, 4- [3-alkoxyalkoxy (C2-20)
-4,4,4-trifluorobutyl] benzoic acid 4'-al
Coxy (C3-C20) carbonyl-4-biphenyli
4- [4-alkoxyalkoxy (C2-20)
−5,5,5-trifluoropentyl] benzoic acid 4′-a
Lucoxy (3-20 carbon atoms) carbonyl-4-biphenyl
Ryl, 4- [5-alkoxyalkoxy (having 2 to 20 carbon atoms)
-6,6,6-trifluorohexyl] benzoic acid 4'-a
Lucoxy (3-20 carbon atoms) carbonyl-4-biphenyl
Ryl, 4- [6-alkoxyalkoxy (C2-20)
-7,7,7-trifluoroheptyl] benzoic acid 4'-a
Lucoxy (3-20 carbon atoms) carbonyl-4-biphenyl
Ryl, 4- [2-alkoxyalkoxy (C2-20)
-3,3,3-trifluoropropyl] benzoic acid 4'-a
Alkyl (3 to 20 carbon atoms) carbonyloxy-4-biph
Enylyl, 4- [3-alkoxyalkoxy (C2-20)
-4,4,4-trifluorobutyl] benzoic acid 4'-al
Killed (C3-C20) carbonyloxy-4-biphe
Niryl, 4- [4-alkoxyalkoxy (C2-20)
−5,5,5-trifluoropentyl] benzoic acid 4′-a
Alkyl (3 to 20 carbon atoms) carbonyloxy-4-biph
Enylyl, 4- [5-alkoxyalkoxy (C2-20)
-6,6,6-trifluorohexyl] benzoic acid 4'-a
Alkyl (3 to 20 carbon atoms) carbonyloxy-4-biph
Enylyl, 4- [6-alkoxyalkoxy (C2-20)
-7,7,7-trifluoroheptyl] benzoic acid 4'-a
Alkyl (3 to 20 carbon atoms) carbonyloxy-4-biph
Enylyl, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20, 2- [4- [4- [3-alkoxyalkoxy (carbon
2-4) -4,4,4-trifluorobutyl] phenyl
Carbonyloxy] phenyl] -5-alkoxy (carbon
Pyrimidine having the number of 3 to 20, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20; 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20, 2- [4- [4- [6-alkoxyalkoxy (carbon
-7,7,7-trifluoroheptyl] pheny
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Pyrimidine having a prime number of 3 to 20, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20; 2- [4- [4- [3-alkoxyalkoxy (carbon
2-4) -4,4,4-trifluorobutyl] phenyl
Carbonyloxy] phenyl] -5-alkyl (carbon number
3-20) pyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20, 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20, 2- [4- [4- [6-alkoxyalkoxy (carbon
-7,7,7-trifluoroheptyl] pheny
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Pyrimidine having the number of 3 to 20, 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine having a prime number of 3 to 20, 2- [4- [4- [3-alkoxyalkoxy (carbon
2-4) -4,4,4-trifluorobutyl] phenyl
Carbonyloxy] phenyl] -5-alkoxy (carbon
Carbonylpyrimidine of the number 3 to 20) 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (having a prime number of 3 to 20), 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] phenyi
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine having a prime number of 3 to 20, 2- [4- [4- [6-alkoxyalkoxy (carbon
-7,7,7-trifluoroheptyl] pheny
Rucarbonyloxy] phenyl] -5-alkoxy (charcoal
Carbonylpyrimidine (having a prime number of 3 to 20), 2- [4- [4- [2-alkoxyalkoxy (carbon
2-3) -3,3,3-trifluoropropyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine of the number 3-20), 2- [4- [4- [3-alkoxyalkoxy (carbon
2-4) -4,4,4-trifluorobutyl] phenyl
Carbonyloxy] phenyl] -5-alkyl (carbon number
3-20) carbonyloxypyrimidine, 2- [4- [4- [4-alkoxyalkoxy (carbon
2-5) -5,5,5-trifluoropentyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine of the number 3-20), 2- [4- [4- [5-alkoxyalkoxy (carbon
2-6) -6,6,6-trifluorohexyl] phenyi
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine of the number 3-20), 2- [4- [4- [6-alkoxyalkoxy (carbon
-7,7,7-trifluoroheptyl] pheny
Rucarbonyloxy] phenyl] -5-alkyl (carbon
Carbonyloxypyrimidine of the number 3-20), 4- [2-alkyl (C1-20) carbonyl
[Xy-3,3,3-trifluoropropyl] benzoic acid 4-
Alkoxy (3-20 carbon) phenyl, 4- [3-alkyl (1-20 carbon) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4-A
Alkoxy (3 to 20 carbon) phenyl, 4- [4-alkyl (1 to 20 carbon) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4-
Alkoxy (3-20 carbon) phenyl, 4- [5-alkyl (1-20 carbon) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4-
Alkoxy (3-20 carbon) phenyl, 4- [6-alkyl (1-20 carbon) carbonyl
[Xy-7,7,7-trifluoroheptyl] benzoic acid 4-
Alkoxy (3-20 carbon) phenyl, 4- [2-alkyl (1-20 carbon) carbonyl
[Xy-3,3,3-trifluoropropyl] benzoic acid 4-
Alkyl (C3-C20) phenyl, 4- [3-alkyl (C1-C20) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4-A
Alkyl (C3-C20) phenyl, 4- [4-alkyl (C1-C20) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4-
Alkyl (C3-C20) phenyl, 4- [5-alkyl (C1-C20) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4-
Alkyl (C3-C20) phenyl, 4- [6-alkyl (C1-C20) carbonyl
[Xy-7,7,7-trifluoroheptyl] benzoic acid 4-
Alkyl (having 3 to 20 carbon atoms) phenyl, 4- [2-alkyl (having 1 to 20 carbon atoms) carbonyl
[Xy-3,3,3-trifluoropropyl] benzoic acid 4-
Alkoxy (3-20 carbon) carbonylphenyl, 4- [3-alkyl (1-20 carbon) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4-A
Alkoxy (3-20 carbon) carbonylphenyl, 4- [4-alkyl (1-20 carbon) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4-
Alkoxy (3-20 carbon) carbonylphenyl, 4- [5-alkyl (1-20 carbon) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4-
Alkoxy (3-20 carbon) carbonylphenyl, 4- [6-alkyl (1-20 carbon) carbonyl
[Xy-7,7,7-trifluoroheptyl] benzoic acid 4-
Alkoxy (3-20 carbon) carbonylphenyl, 4- [2-alkyl (1-20 carbon) carbonyl
[Xy-3,3,3-trifluoropropyl] benzoic acid 4-
Alkyl (C3-C20) carbonyloxyphenyl
4- [3-alkyl (C 1-20) carbonyl]
Xy-4,4,4-trifluorobutyl] benzoic acid 4-A
Alkyl (3-20 carbon) carbonyloxyphenyl, 4- [4-alkyl (1-20 carbon) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4-
Alkyl (C3-C20) carbonyloxyphenyl
4- [5-alkyl (C1-20) carbonyl]
[Xy-6,6,6-trifluorohexyl] benzoic acid 4-
Alkyl (C3-C20) carbonyloxyphenyl
4- [6-alkyl (C1-20) carbonyl]
[Xy-7,7,7-trifluoroheptyl] benzoic acid 4-
Alkyl (C3-C20) carbonyloxyphenyl
4- [2-alkyl (C1-20) carbonyl]
Xy-3,3,3-trifluoropropyl] benzoic acid 4 '
-Alkoxy (C3-C20) -4-biphenylyl, 4- [3-alkyl (C1-C20) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4'-
Alkoxy (C 3-20) -4-biphenylyl, 4- [4-alkyl (C 1-20) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4 '
-Alkoxy (C 3-20) -4-biphenylyl, 4- [5-alkyl (C 1-20) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4 '
-Alkoxy (C3-20) -4-biphenylyl, 4- [6-alkyl (C1-20) carbonyl
Xy-7,7,7-trifluoroheptyl] benzoic acid 4 '
-Alkoxy (C3-20) -4-biphenylyl, 4- [2-alkyl (C1-20) carbonyl
Xy-3,3,3-trifluoropropyl] benzoic acid 4 '
-Alkyl (C3-20) -4-biphenylyl, 4- [3-alkyl (C1-20) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4'-
Alkyl (C3-C20) -4-biphenylyl, 4- [4-alkyl (C1-C20) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4 '
-Alkyl (C3-C20) -4-biphenylyl, 4- [5-alkyl (C1-C20) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4 '
-Alkyl (C3-20) -4-biphenylyl, 4- [6-alkyl (C1-20) carbonyl
Xy-7,7,7-trifluoroheptyl] benzoic acid 4 '
-Alkyl (C3-20) -4-biphenylyl, 4- [2-alkyl (C1-20) carbonyl
Xy-3,3,3-trifluoropropyl] benzoic acid 4 '
-Alkoxy (3-20 carbon) carbonyl-4-biph
Enylyl, 4- [3-alkyl (C 1-20) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4'-
Alkoxy (C3-C20) carbonyl-4-biphe
Nilyl, 4- [4-alkyl (C 1-20) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4 '
-Alkoxy (3-20 carbon) carbonyl-4-biph
Enylyl, 4- [5-alkyl (C 1-20) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4 '
-Alkoxy (3-20 carbon) carbonyl-4-biph
Enylyl, 4- [6-alkyl (C 1-20) carbonyl
Xy-7,7,7-trifluoroheptyl] benzoic acid 4 '
-Alkoxy (3-20 carbon) carbonyl-4-biph
Enylyl, 4- [2-alkyl (C 1-20) carbonyl
Xy-3,3,3-trifluoropropyl] benzoic acid 4 '
-Alkyl (C3-20) carbonyloxy-4-
Biphenylyl, 4- [3-alkyl (C 1-20) carbonyl
Xy-4,4,4-trifluorobutyl] benzoic acid 4'-
Alkyl (C3-C20) carbonyloxy-4-bi
Phenylyl, 4- [4-alkyl (C 1-20) carbonyl
Xy-5,5,5-trifluoropentyl] benzoic acid 4 '
-Alkyl (C3-20) carbonyloxy-4-
Biphenylyl, 4- [5-alkyl (C 1-20) carbonyl
[Xy-6,6,6-trifluorohexyl] benzoic acid 4 '
-Alkyl (C3-20) carbonyloxy-4-
Biphenylyl, 4- [6-alkyl (C 1-20) carbonyl
Xy-7,7,7-trifluoroheptyl] benzoic acid 4 '
-Alkyl (C3-20) carbonyloxy-4-
Biphenylyl, 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-3,3,3-trifluoropropyl]
Enylcarbonyloxy] phenyl] -5-alkoxy
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nylcarbonyloxy] phenyl] -5-alkoxy
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Pyrimidine (having 3 to 20 carbon atoms) 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)
Carbonyloxy-3,3,3-trifluoropropyl]
Phenylcarbonyloxy] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nilcarbonyloxy] phenyl] -5-alkyl (charcoal
Pyrimidine having a prime number of 3 to 20), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Pyrimidine (having 3 to 20 carbon atoms) 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)
Carbonyloxy-3,3,3-trifluoropropyl]
Enylcarbonyloxy] phenyl] -5-alkoxy
Carbonylpyrimidine (having 3 to 20 carbon atoms) 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)
Carbonyloxy-4,4,4-trifluorobutyl]
Nylcarbonyloxy] phenyl] -5-alkoxy
Carbonylpyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [4-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-5,5,5-trifluoropentyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Carbonylpyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Carbonylpyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
Enylcarbonyloxy] phenyl] -5-alkoxy
Carbonylpyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [2-alkyl (having 1 to 20 carbon atoms)
Carbonyloxy-3,3,3-trifluoropropyl]
Phenylcarbonyloxy] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [3-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-4,4,4-trifluorobutyl]
Nilcarbonyloxy] phenyl] -5-alkyl (charcoal
Carbonyloxypyrimidine (having a prime number of 3 to 20), 2- [4- [4- [4-alkyl (having a carbon number of 1 to 20)]
Carbonyloxy-5,5,5-trifluoropentyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [5-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-6,6,6-trifluorohexyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 2- [4- [4- [6-alkyl (having 1 to 20 carbon atoms)]
Carbonyloxy-7,7,7-trifluoroheptyl] f
Phenylcarbonyloxy] phenyl] -5-alkyl
Carbonyloxypyrimidine (having 3 to 20 carbon atoms), 4- [2-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4-alkoxy (C3-C20) phenyl, 4- [3-alkoxyalkyl (C2-C20)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
4-alkoxy (C3-20) phenyl, 4- [4-alkoxyalkyl (C2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4-alkoxy (C3-20) phenyl, 4- [5-alkoxyalkyl (C2-20) carb
Bonyloxy-6,6,6-trifluorohexyl] benzoate
Acid 4-alkoxy (C3-20) phenyl, 4- [6-alkoxyalkyl (C2-20)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4-alkoxy (C3-20) phenyl, 4- [2-alkoxyalkyl (C2-20) ca
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4-alkyl (3-20 carbon) phenyl, 4- [3-alkoxyalkyl (2-20 carbon) perfume
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
4-alkyl (phenylene having 3 to 20 carbon atoms) phenyl, 4- [4-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4-alkyl (3 to 20 carbon) phenyl, 4- [5-alkoxyalkyl (2 to 20 carbon) perfume
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4-alkyl (3-20 carbon atoms) phenyl, 4- [6-alkoxyalkyl (2-20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4-alkyl (3-20 carbon) phenyl, 4- [2-alkoxyalkyl (2-20 carbon) perfume
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4-alkoxy (C3-C20) carbonyl phthalate
Phenyl, 4- [3-alkoxyalkyl (C 2-20)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
Acid 4-alkoxy (3-20 carbon) carbonyl
Nil, 4- [4-alkoxyalkyl (C 2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4-alkoxy (C3-C20) carbonyl phthalate
Phenyl, 4- [5-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4-alkoxy (C3-C20) carbonyl phthalate
Phenyl, 4- [6-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4-alkoxy (C3-C20) carbonyl phthalate
Phenyl, 4- [2-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4-alkyl carboxylate having 3 to 20 carbon atoms
Cyphenyl, 4- [3-alkoxyalkyl (C2-20)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
4-alkyl carbonyloxy (having 3 to 20 carbon atoms)
Phenyl, 4- [4-alkoxyalkyl (C 2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4-alkyl carboxylate having 3 to 20 carbon atoms
Cyphenyl, 4- [5-alkoxyalkyl (C2-20)
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4-alkyl carboxylate having 3 to 20 carbon atoms
Cyphenyl, 4- [6-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4-alkyl carboxylate having 3 to 20 carbon atoms
Cyphenyl, 4- [2-alkoxyalkyl (C2-20)
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4'-Alkoxy acid (3-20 carbon atoms) -4-biph
Enylyl, 4- [3-alkoxyalkyl (2-20 carbon atoms)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
Acid 4'-alkoxy (C3-C20) -4-biphe
Niryl, 4- [4-alkoxyalkyl (C2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4'-Alkoxy acid (3-20 carbon atoms) -4-biph
Enylyl, 4- [5-alkoxyalkyl (C2-20)
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4'-Alkoxy acid (3-20 carbon atoms) -4-biph
Enylyl, 4- [6-alkoxyalkyl (C2-20)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4'-Alkoxy acid (3-20 carbon atoms) -4-biph
Enylyl, 4- [2-alkoxyalkyl (C2-20)
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4'-alkyl fragrance (3-20 carbon atoms) -4-biphe
Niryl, 4- [3-alkoxyalkyl (2-20 carbon atoms)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
4'-alkyl acid (having 3 to 20 carbon atoms) -4-biphenyl
Ryl, 4- [4-alkoxyalkyl (C 2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4'-alkyl fragrance (3-20 carbon atoms) -4-biphe
Nilyl, 4- [5-alkoxyalkyl (C2-20) ca
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4'-alkyl fragrance (3-20 carbon atoms) -4-biphe
Niryl, 4- [6-alkoxyalkyl (C2-20) ca
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4'-alkyl fragrance (3-20 carbon atoms) -4-biphe
Niryl, 4- [2-alkoxyalkyl (C2-20))
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4'-alkoxy (C3-20) carbonyl carboxylic acid
-4-biphenylyl, 4- [3-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
Acid 4'-alkoxy (C3-20) carbonyl-
4-biphenylyl, 4- [4-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4'-alkoxy (C3-20) carbonyl carboxylic acid
-4-biphenylyl, 4- [5-alkoxyalkyl (having 1 to 20 carbon atoms)
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4'-alkoxy (C3-20) carbonyl carboxylic acid
-4-biphenylyl, 4- [6-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4'-alkoxy (C3-20) carbonyl carboxylic acid
-4-biphenylyl, 4- [2-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-3,3,3-trifluoropropyl] benzo
4'-alkyl carboxylate (having 3 to 20 carbon atoms)
Xy-4-biphenylyl, 4- [3-alkoxyalkyl (C2-20)
Rubonyloxy-4,4,4-trifluorobutyl] benzoate
4'-alkyl acid (carbonyl having 3 to 20 carbon atoms)
C-4-biphenylyl, 4- [4-alkoxyalkyl (C2-20)
Rubonyloxy-5,5,5-trifluoropentyl] benzoate
4'-alkyl carboxylate (having 3 to 20 carbon atoms)
Xy-4-biphenylyl, 4- [5-alkoxyalkyl (C2-20)
Rubonyloxy-6,6,6-trifluorohexyl] benzoate
4'-alkyl carboxylate (having 3 to 20 carbon atoms)
Xy-4-biphenylyl, 4- [6-alkoxyalkyl (having 2 to 20 carbon atoms)
Rubonyloxy-7,7,7-trifluoroheptyl] benzoate
4'-alkyl carboxylate (having 3 to 20 carbon atoms)
Xy-4-biphenylyl, 2- [4- [4- [2-alkoxyalkyl (carbon number
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (3-20 carbon) pyrimidine, 2- [4- [4- [3-alkoxyalkyl (carbon number)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenylcarbonyloxy] phenyl] -5-a
Lucoxy (3-20 carbon atoms) pyrimidine, 2- [4- [4- [4-alkoxyalkyl (carbon number)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [5-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (3-20 carbon atoms) pyrimidine, 2- [4- [4- [6-alkoxyalkyl (carbon number)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (3-20 carbon) pyrimidine, 2- [4- [4- [2-alkoxyalkyl (carbon number)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [3-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenylcarbonyloxy] phenyl] -5-a
Alkyl (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [4-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [5-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [6-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (having 3 to 20 carbon atoms) pyrimidine, 2- [4- [4- [2-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (having 3 to 20 carbon atoms) carbonylpyrimidine, 2- [4- [4- [3-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenylcarbonyloxy] phenyl] -5-a
Carbonyl (3-20 carbon atoms) carbonyl pyrimidine, 2- [4- [4- [4-alkoxyalkyl (carbon number)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (3-20 carbon atoms) carbonylpyrimidine, 2- [4- [4- [5-alkoxyalkyl (carbon number)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (having 3 to 20 carbon atoms) carbonylpyrimidine, 2- [4- [4- [6-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenylcarbonyloxy] phenyl] -5-
Alkoxy (having 3 to 20 carbon atoms) carbonylpyrimidine, 2- [4- [4- [2-alkoxyalkyl (having carbon atoms)
2-20) carbonyloxy-3,3,3-trifluoroprop
Ropyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (C3-20) carbonyloxypyrimidi
2- [4- [4- [3-alkoxyalkyl (carbon number)
2-20) carbonyloxy-4,4,4-trifluorobu
Tyl] phenylcarbonyloxy] phenyl] -5-a
Alkyl (3 to 20 carbon atoms) carbonyloxypyrimidi
2- [4- [4- [4-alkoxyalkyl (carbon number)
2-20) carbonyloxy-5,5,5-trifluorope
[Nthyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (C3-20) carbonyloxypyrimidi
2- [4- [4- [5-alkoxyalkyl (carbon number)
2-20) carbonyloxy-6,6,6-trifluoro
Xyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (C3-20) carbonyloxypyrimidi
2- [4- [4- [6-alkoxyalkyl (carbon number)
2-20) carbonyloxy-7,7,7-trifluoro
[Butyl] phenylcarbonyloxy] phenyl] -5-
Alkyl (C3-20) carbonyloxypyrimidi
Etc. According to the production method described above, the tough represented by the general formula [1]
Optically active aromatic compounds having a trifluoromethyl group
The compound is obtained by using a liquid crystal material, particularly a ferroelectric liquid crystal material.
When using as a material, consider practical optical stability, etc.
Taking into account, the substituent R of the general formula [1]^TwoIs a halogen atom
Unsubstituted alkyl or alkoxyalkyl
It is preferably a group. In addition, those that show more favorable physical properties when put into practical use
As a substituent R^TwoIs an alkyl group having 1 to 10 carbon atoms or
Those which are alkoxyalkyl groups are exemplified. Substituent R¹About more practically, the carbon number of 8 to 16
Although an alkyl group is preferable, it is used as a component of a liquid crystal material.
In this case, there is no particular limitation. In the general formula [1], when X is -COO-
Shows practical properties in some cases. In addition, high-speed response,
In order to demonstrate the response, the spontaneous polarization value of the liquid crystal compound must be
Although a large one is preferable, it is represented by the general formula [1] of the present invention.
Active Aromatic Compound Having Trifluoromethyl Group
Objects have a dipole moment at the asymmetric carbon as a structural feature
Large trifluoromethyl group is directly connected,
Accordingly, a large spontaneous polarization value can be obtained. Especially,
When n is 0 in the general formula [1], this characteristic becomes remarkable.
Express. The optical activity having a trifluoromethyl group of the present invention
Aromatic compound [1] alone exhibits liquid crystal phase
Of course, even if it does not exhibit a liquid crystal phase,
Can be effectively used as a component of the liquid crystal composition
You. In the present invention, the liquid crystal composition is represented by the general formula [1].
Optically Active Aromatic Having Trifluoromethyl Group
Compounds containing at least one compound
It is. In this case, an optically active having a trifluoromethyl group
The aromatic compound [1] is used in an amount of 0.1 to 99.
9% by weight, preferably 1 to 99% by weight
Is good. Further, such a liquid crystal composition is used for a liquid crystal element, for example, an optical
It is used effectively by using it for a switching element,
In this case, the method of using the liquid crystal composition is known in the art.
The law is applied as it is and is not particularly limited. <Effects of the Invention> Thus, the trif 示 le represented by the general formula [1] of the present invention is obtained.
Optically active aromatic compounds having an oromethyl group are
It has very excellent properties as a material,
As a liquid crystal element using this.
Can be used. Further, according to the production method of the present invention, the compound
Inexpensive and easily obtained. <Example> Hereinafter, the present invention will be described with reference to raw material production examples and examples.
However, the present invention is not limited thereby. Production Example 1 Four ports equipped with thermometer, dropping funnel and stirrer
2.4 g (0.1 mol) of magnesium pieces in a flask and anhydrous
Charge 50 ml of tetrahydrofuran, and add 4-benzyloxy
2.6 g (10 mmol) of bromobenzene and anhydrous tetrahydro
Add a mixture of 5 ml of furan and a small amount of iodine and raise to 60 ° C
Warm and add 23.7 g of 4-benzyloxybromobenzene
Of anhydrous tetrahydrofuran and 45 ml of anhydrous tetrahydrofuran were added dropwise. drop
After completion of the lower step, the mixture was stirred under reflux for 2 hours, and then cooled to room temperature.
Rejected. The mixture is treated at −78 ° C. with trifluoroacetic anhydride 3
1.5 g (0.15 mol) and 150 ml of anhydrous tetrahydrofuran
Was dropped into the mixture. After dropping, stir at -78 ° C for 1 hour.
After stirring, the temperature was gradually raised to -50 ° C. Saturated salt at the same temperature
100 ml of aqueous ammonium chloride solution was added, and the temperature was raised to room temperature. This
300 ml of ether was added to the mixture and extracted.
The organic layer was washed with a 5% aqueous solution of sodium bicarbonate, water, and saturated saline in this order.
After drying over magnesium sulfate, the mixture was concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography.
-(Eluent: toluene / hexane = 1/2)
Benzyloxy-α, α, α-trifluoroacetophen
Non- [5] 18.2 g (65% yield) was obtained as a pale yellow solid.
Was. Melting point: 58-60C). 16.8 g (60 mmol) of [5] obtained here was
Dissolve in 50 ml and add sodium borohydride 1.1 g (30 mM
) And stirred at room temperature for 4 hours. After the reaction,
The mixture was poured into water and extracted with ethyl acetate. Get
The organic layer was washed with water and saturated saline in this order,
After drying over magnesium, the mixture was concentrated under reduced pressure to give 4-benzylthio.
Xy-α, α, α-trifluoro-β-phenethylal
16.7 g (99% yield) of coal [6] was obtained as a pale yellow solid.
Was. Melting point: 115-117 ° C. 15.5 g (55 mmol) of [6] obtained here was
acetyl chloride at 0-5 ° C (5.2 g, 66 mM).
) And stirred at the same temperature for 2 hours. After the reaction is completed, the reaction mixture is poured into water, and the ethyl acetate is added.
Extracted. The obtained organic layer was washed with 10% hydrochloric acid, water and 5%
Wash with aqueous sodium chloride solution and saturated saline, and dry with anhydrous magnesium sulfate.
After drying, the mixture was concentrated under reduced pressure to give 4-benzyloxy-1- (1
-Acetoxy-2,2,2-trifluoroethyl) benzene
[7-1] 17.8 g (yield 100%) was obtained as a pale yellow solid
Was. 85-87 ° C. 17.8 g (55 mmol) of [7-1] obtained here
Dissolve in 10 ml of form, 300 ml of 0.3 M phosphate buffer and
1.8 g of Pase (Amano P) and intensify at 36-38 ° C for 48 hours
Stirred well. After completion of the reaction, the reaction mixture was filtered, and the filtrate was ethyl acetate.
And the obtained organic layer was washed with saturated saline.
After drying over anhydrous magnesium sulfate,
Concentrated. The obtained residue is subjected to silica gel column chromatography.
Chromatography (eluent: toluene) to give (-)-4-
Benzyloxy-1- (1-acetoxy-2,2,2-tri
Fluoroethyl) benzene 9.3 g (52% yield), [α] D
²⁰= −33.6 ゜ (c = 1, CHCl_Three)) And (+)-4-b
Ndyloxy-α, α, α-trifluoro-β-phene
7.3 g of tyl alcohol [8-1] (yield 47%, [α] D²⁰
= + 16.2 ゜ (c = 1, CHCl_Three) Got. The obtained (-)-4-benzyloxy-1- (1-
Acetoxy-2,2,2-trifluoroethyl) benzene 8.1
g (25 mmol) dissolved in 50 ml of methanol,
Add 20 ml of aqueous sodium chloride solution and stir at room temperature for 1 hour
Was. After completion of the reaction, the reaction mixture was poured into water, and ethyl acetate was added.
Extracted. Wash the obtained organic layer with water and saturated saline.
And dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure.
And (-)-4-benzyloxy-α, α, α-trif
6.9 g of fluoro-β-phenethyl alcohol [8-2] (yield
Rate 98%), [α] D²⁰= -14.1 ゜ (c = 1, CHCl_ThreeGet))
Was. Production Example 2 1.4 g (5 mmol) of [8-1] obtained in Production Example 1
Dissolve in 20 ml of tilformamide and add sodium hydride (including
0.24 g (6 mmol) and stirred at room temperature for 1 hour.
Stirred. Then, 1.5 g of n-hexyl p-toluenesulfonate
(6 mmol) and stirred at room temperature for 3 hours. End of reaction
After completion, the reaction mixture was poured into water and extracted with ethyl acetate.
The obtained organic layer was washed with water and saturated saline,
After drying with magnesium acid, it was concentrated under reduced pressure. Obtained residue
The residue is subjected to silica gel column chromatography (eluent:
(Ruene / hexane = 1/1) to give (+)-4-benzyl
Loxy-1- (1-hexyloxy-2,2,2-trif
1.6 g of (fluoroethyl) benzene [9-1] (88% yield,
[Α] D²⁰= + 36.6 ゜ (c = 1, CHCl_Three)). Production Examples 3 to 6 p-toluene used as an alkylating agent in Production Example 2
Alkyl described in Table 1 in place of n-hexyl sulfonic acid
The reaction was carried out in the same manner as in Production Example 2 except that the agent [12] was used.
And after work-up, the optically active benzyl described in Table 1.
Oxybenzene derivatives

[9] was obtained. The results are shown in Table 1. Production Example 7-9 p-toluene used as an alkylating agent in Production Example 2 using [8-2] obtained in Production Example 1 as a raw material instead of [8-1] used as a raw material in Production Example 2 The reaction and post-treatment were carried out according to Production Example 2 except that the alkylating agent [12] shown in Table 2 was used instead of n-hexyl sulfonate. Table 2 shows the results. Production Example 10 0.85 g (3 mmol) of [8-2] obtained in Production Example 1 was dissolved in 10 ml of pyridine, cooled to 0 to 5 ° C., and 0.48 g (3.6 mmol) of hexanoyl chloride was added. For 2 hours. After the completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and saturated saline in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (-)-4-benzyloxy-1- ( 1.14 g of 1-hexanoyloxy-2,2,2-trifluoroethyl) benzene [9-9] (yield 100%,
[Α] D ²⁰ = −57.0 ° (c = 1, CHCl ₃ )) was obtained. Production Examples 11 and 12 The reaction and post-treatment were carried out in the same manner as in Production Example 10 except that the acylating agent [11] shown in Table 3 was used instead of the hexanoyl chloride used as the acylating agent in Production Example 10. Was done. The results are shown in Table-3. Production Example 13 1.1 g (3 mmol) of [9-1] obtained in Production Example 2 was dissolved in a mixture of 80 ml of tetrahydrofuran and 20 ml of methanol, and 0.2 g of 10% Pd / C was added.
Stir vigorously for hours. After completion of the reaction, Pd / C was filtered off, and the obtained filtrate was concentrated to give (+)-4- (1-hexyloxy-2,2,2-trifluoroethyl) phenol [3-1] 0.82 g (yield 99
%, [Α] D20 = + 44.0 ° (c = 1, CHCl 3). Production Examples 14 to 23 Various optically active benzyloxybenzene derivatives obtained in Production Examples 3 to 12 in place of [9-1] used as a raw material in Production Example 13

The reaction and post-treatment were carried out in the same manner as in Production Example 13 except for using [9]. The results are shown in Table-4. Production Example 24 A four-necked flask equipped with a thermometer, a dropping funnel and a stirrer was charged with 4.8 g (0.2 mol) of magnesium pieces and 100 ml of anhydrous tetrahydrofuran.
A mixture of 4.0 g (20 mmol) of phenylpropane and 10 ml of anhydrous tetrahydrofuran and a small amount of iodine were added, the temperature was raised to 60 ° C., and the same temperature was applied to 35.8 of 1-bromo-3-phenylpropane.
A mixture of g (0.18 mol) and 90 ml of anhydrous tetrahydrofuran was added dropwise. After completion of the dropwise addition, the mixture was stirred under reflux for 2 hours, and then cooled to room temperature. This mixture was added dropwise at −78 ° C. to a mixture of 31.3 g (0.22 mol) of ethyl trifluoroacetate and 200 ml of anhydrous tetrahydrofuran. After completion of the dropwise addition, the mixture was stirred at −78 ° C. for 2 hours, and then −50 ° C.
The temperature was gradually raised until the temperature was increased, and the mixture was further stirred at the same temperature for 2 hours. After completion of the reaction, 100 ml of 1N hydrochloric acid was added at −50 ° C., and then
The temperature was raised to room temperature. 300 ml of ether was added to the reaction mixture for extraction, and the obtained organic layer was washed with water, 5% aqueous sodium hydrogen carbonate and saturated brine in that order, dried over anhydrous magnesium sulfate, and then dried.
It was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: toluene / hexane = 1/4) to give 5-phenyl-1,1,1-trifluoropentan-2-one [14
-1] 20.3 g (yield 47%) was obtained. [14-
1] 19.5 g (90 mmol) is dissolved in 200 ml of ethanol,
Add 1.7 g (45 mmol) of sodium borohydride,
Stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 5-phenyl-1,1,1-trifluoro-2-pentanol [15-1. 19.1 g (yield 97
%) As a colorless liquid. 18.5 g (85 mmol) of [15-1] obtained here was dissolved in 100 ml of pyridine, 7.1 g (90 mmol) of acetyl chloride was added at 0 to 5 ° C, and the mixture was stirred at the same temperature for 2 hours. After the reaction,
The reaction mixture was poured into water and extracted with ethyl acetate.
The obtained organic layer was washed successively with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and concentrated to give 2-acetoxy-5-phenyl-1,1,1. 1−
21.7 g (98% yield) of trifluoropentane [16-1] was obtained as a pale yellow liquid. Next, 21.3 g (0.16 mol) of aluminum chloride was placed in a four-necked flask equipped with a thermometer, a dropping funnel and a stirrer.
And 200 ml of anhydrous dichloromethane, and 12.6 g (0.16 mol) of acetyl chloride was further added thereto, followed by stirring at room temperature for 1 hour. The mixture was cooled to 0-5 ° C. and obtained above at the same temperature [16
-1] 20.8 g (80 mmol) and 100 ml of anhydrous dichloromethane
Was added dropwise. After the addition, the mixture was stirred at the same temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The obtained organic layer was washed with 10% hydrochloric acid, water, and 5%.
% Sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: toluene / hexane = 2/1) to give 4-
20.1 g (83% yield) of (4-acetoxy-5,5,5-trifluoropentyl) acetophenone [17-1] was obtained. 19.6 g (65 mmol) of [17-1] obtained here was dissolved in 10 ml of chloroform, 300 ml of 0.3 M phosphate buffer and 2.0 g of lipase (Amano P) were added, and the mixture was vigorously stirred at 36 to 38 ° C. for 36 hours. After completion of the reaction, the reaction mixture was filtered, the filtrate was extracted with ethyl acetate, and the obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: toluene) to give (-)-4- (4-
8.1 g of hydroxy-5,5,5-trifluoropentyl) acetophenone [18-1] (yield 48%, [α] D ²⁰ = −3.6 ゜ (c = 1, CHCl ₃ )) and (−)-4 -(4-acetoxy-5,5,5-trifluoropentyl) acetonephenone [18-2] 9.8 g (yield 50%, [α] D ² O = -4.1 ゜ (c =
1, CHCl ₃ )) was obtained. Production Examples 25 and 26 Production Example 24 was repeated except that 1-bromo-2-phenylethane or 1-bromo-4-phenylbutane was used instead of 1-bromo-3-phenylpropane used as a raw material in Production Example 24. Reaction and post-treatment were carried out in the same manner. The results are shown in Table-5. Production Example 27 A mixture of 1.3 g (5 mmol) of [18-1] obtained in Production Example 24, 8.5 g (50 mmol) of propyl iodide, and 3.5 g (15 mmol) of silver oxide was violently shielded from light at room temperature for 48 hours. Stirred. The obtained reaction mixture was filtered, and the filtrate was filtered with ethyl acetate 50.
Washed with ml. The filtrate combined with the washing solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (eluent: toluene) to give (-)-4- (4-propoxy-5,5,5-trifluoropentyl). Acetophenone (25
-1] 1.3 g (86% yield), [α] D ²⁰ = -2.7 ゜ (c = 1,
CHCl ₃ )) was obtained. 0.60 g (2 mmol) of [25-1] obtained here was dissolved in 10 ml of dichloromethane, and 0.52 g of m-chloroperbenzoic acid was dissolved.
(3 mmol) and stirred at room temperature for 24 hours. After completion of the reaction, 20 ml of 5% aqueous sodium bisulfite solution was added to the reaction mixture, and the mixture was stirred for 30 minutes, and extracted with ethyl acetate. The obtained organic layer was washed with water, 5% aqueous sodium hydrogen carbonate and saturated saline in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain (+)-4- (4-propoxy-5,5,5). 5-trifluoropentyl) -1-acetoxybenzene [26-
1] 0.61 g (98% yield, [α] D ²⁰ = + 2.6 ＋ (c = 1, CHC
l ₃ )) got. 0.60 g (1.9 mmol) of [26-1] obtained here was dissolved in 10 ml of methanol, 1.5 ml of a 10% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 1N hydrochloric acid was added to the reaction mixture until the pH became 1 to 2, and then extracted with ethyl acetate. The obtained organic layer was washed with water, 5% aqueous sodium hydrogen carbonate and saturated saline in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (-)-
0.51 g of 4- (4-propoxy-5,5,5-trifluoropentyl) phenol [3-14] (100% yield, [α] D
²⁰ = −3.0 ° (c = 1, CHCl ₃ )). Production Examples 28 to 35 Instead of [18-1] used as a raw material in Production Example 27 and propyl iodide used as an alkylating agent, optically active acetophenone derivatives [18] and an alkylating agent described in Table 6 were used. The reaction and post-treatment were carried out in the same manner as in Production Example 27 except for using [12]. The results are shown in Table-6. Production Example 36 9.1 g (30 mmol) of [18-2] obtained in Production Example 24 was dissolved in 50 ml of dichloromethane, and 7.8 g of m-chloroperbenzoic acid was obtained.
(45 mmol) and stirred at room temperature for 36 hours. After completion of the reaction, the reaction mixture was diluted with 150 ml of ethyl acetate, washed successively with 10% aqueous sodium hydrogen sulfite, water, 5% aqueous sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. +)-(4-Acetoxy-5,5,5-trifluoropentyl) -1-acetoxybenzene [19-1]
9.1 g (96% yield, [α] D ²⁰ = + 3.1 ゜ (c = 1, CHC
l ₃ )) got. 8.9 g (28 mmol) of the obtained [19-1] was dissolved in methanol (30 ml), 10% aqueous sodium hydroxide solution (30 ml) was added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 1N hydrochloric acid was added until the pH became 1 to 2, and then extracted with ethyl acetate. The obtained organic layer is washed with water, 5
% Sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (+)-(4-hydroxy-5,5,5-trifluoropentyl) phenol [20].
-1] 6.4 g (yield 98%, [α] D ²⁰ = + 4.2 ゜ (c = 1, CH
Cl ₃₎₎ was obtained. The obtained [20-1] was dissolved in 6.3 g (27 mmol) of dimethylformamide (50 ml), and benzyl chloride (5.1 g, 40 mmol) and potassium carbonate (8.3 g, 60 mmol) were added.
Stirred at 6060 ° C. for 5 hours. After the completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (eluent: toluene) to give (+)-4- (4-hydroxy-5,5-5-trifluoropentyl) -1-benzyloxybenzene [21-1]. 8.2 g (94% yield,
[Α] D ²⁰ = + 2.9 ° (c = 1, CHCl ₃ )) was obtained. Production Examples 37 and 38 Same as Production Example 36 except that the optically active acetophenone derivative [18] obtained in Production Example 25 or 26 was used as a raw material instead of [18-2] used as a raw material in Production Example 36. The reaction and after-treatment were carried out. The results are shown in Table-7. Production Example 39 0.97 g (3 mmol) of [21-1] obtained in Production Example 36 was dissolved in 10 ml of dimethylformamide, and 0.16 g (4 mmol) of sodium hydride (content 60%) was added, followed by stirring at room temperature for 1 hour. did. Then, 0.55 g (4 mmol) of butyl bromide
Was added and stirred at 40-50 ° C. for 3 hours. After the completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: toluene / hexane = 1/1) to give (+)
1.1 g of 4- (4-butoxy-5,5,5-trifluoropentyl) -1-benzyloxybenzene [22-1] (93% yield, [α] D ²⁰ = + 2.6} (c = 1, CHCl ₃ )) was obtained. Production Examples 40 to 44 In place of [21-1] used as a raw material in Production Example 39 and butyl bromide used as an alkylating agent, optically active alcohols [21] and an alkylating agent shown in Table 8 were used. The reaction and post-treatment were carried out in the same manner as in Production Example 39 except for using [12]. The results are shown in Table-8. Production Example 45 0.97 g (3 mmol) of [21-1] obtained in Production Example 36 was dissolved in 10 ml of pyridine, and propionic acid chloride was added at 0 to 5 ° C.
0.37 g (4 mmol) was added, and the mixture was stirred at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed successively with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and concentrated to give (-)-4- (4-propanoyloxy). −5,5,5-trifluoropentyl) -1-benzyloxybenzene [22-17] 1.1 g (97% yield,
[Α] D ²⁰ = −3.3 ° (c = 1, CHCl ₃ )) was obtained. Production Examples 46 to 50 In place of [21-1] used as a raw material in Production Example 45 and propionyl chloride used as an acylating agent,
The reaction and post-treatment were carried out in the same manner as in Production Example 45 except that the optically active alcohol [21] and the acylating agent [11] described in 9 were used. The results are shown in Table-9. Production Example 51 0.95 g (2.5 mmol) of [22-1] obtained in Production Example 39 was dissolved in 50 ml of ethanol, and 0.1 g of 10% (Pd / C) was added. Stirred. After the completion of the reaction, Pd / C was separated by filtration, and the obtained filtrate was concentrated under reduced pressure.
0.72 g of (+)-4- (4-butoxy-5,5,5-trifluoropentyl) phenol [3-23] (99% yield,
[Α] D ²⁰ = −2.9 ° (c = 1, CHCl ₃ )) was obtained. Production Examples 52 to 62 In the same manner as in Production Example 51 except that various benzyloxybenzene derivatives [22] obtained in Production Examples 40 to 50 were used instead of [22-1] used as a raw material in Production Example 51, Reaction and work-up were performed. The results are shown in Table-10. Production Example 63 A 20% aqueous sodium hydroxide solution (20 ml) was charged into a four-necked flask equipped with a thermometer, a dropping funnel and a stirrer,
Cooled to 0-5 ° C. 2.6 g (16 mmol) of bromine was added thereto at the same temperature, and the mixture was stirred for 30 minutes. To the resulting mixture, 60 g of [25-1] obtained in Production Example 27 (2
Mmol) and 20 ml of dioxane were added dropwise at 0 to 5 ° C., and after completion of the addition, the mixture was stirred at the same temperature for 8 hours. After the reaction, 2.0 g of sodium bisulfite was added to the reaction mixture.
After stirring for 30 minutes, 10% hydrochloric acid was added until a pH of 1 to 2 was reached, followed by extraction with ether. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (+)-4- (4-propoxy-5,5,5-trifluoropentyl) benzoic acid [ 28−
1] 0.59 g (98% yield, [α] D ²⁰ = + 4.3 ＋ (c = 1, CHC
l ₃ )) got. Production Examples 64 to 71 Production Example 63 was replaced with [25-1] used as a raw material in Production Example 63, except that various optically active acetophenone derivatives [25] obtained in Production Examples 28 to 35 were used as raw materials. Reaction and post-treatment were carried out in the same manner. The results are shown in Table-11. Example 1 In a four-necked flask equipped with a thermometer and a stirrer, 0.28 g (1 mmol) of [3-1] obtained in Production Example 13, 0.36 g (1.3 mmol) of 4-decyloxybenzoic acid and 10 ml of anhydrous dichloromethane were placed. After charging, 0.25 g (1.2 mmol) of N, N'-dicyclohexylcarbodiimide and 20 mg of 4-pyrrolidinopyridine were added, and the mixture was stirred at room temperature for 24 hours. After the completion of the reaction, the resulting precipitate was separated by filtration, and the filtrate was subjected to toluene 50
diluted with water, washed with water, 5% acetic acid, water, 5% aqueous sodium bicarbonate, and saturated saline in this order, and dried over anhydrous magnesium sulfate.
Thereafter, the mixture was concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (eluent: toluene / hexane =
1/1) to give (+)-4-decyloxybenzoic acid 4-
(1-hexyloxy-2,2,2-trifluoroethyl)
0.49 g (92% yield) of phenyl was obtained. Example 2 In a four-necked flask equipped with a thermometer and a stirrer, 0.30 g (1 mmol) of [28-1] obtained in Production Example 63, 0.33 g (1.3 mmol) of 4-decyloxyphenol and 10 ml of anhydrous dichloromethane were placed. After charging, 0.25 g (1.2 mmol) of N, N'-dicyclohexylcarbodiimide and 20 mg of 4-pyrrolidinopyridine were added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, post-treatment was carried out in the same manner as in Example 1, and (+)
0.49 g of 4-decyloxyphenyl-4- (4-propoxy-5,5,5-trifluoropentyl) benzoate (yield 93
%). Examples 3 to 57 The reaction and post-treatment were carried out according to Example 1 or Example 2 except that the raw materials used were changed to those shown in Table 12, and the results shown in Table 12 were obtained. Examples 58 to 62 Using the liquid crystal compounds, liquid crystal compositions shown in Table 13 were prepared. The adjustment was performed by weighing a predetermined compound in a sample bottle by a predetermined weight and mixing while heating and melting. Using the liquid crystal composition thus adjusted, a liquid crystal element was manufactured by the method described below. [Liquid Crystal Element Manufacturing Method] A polyimide polymer film is provided on a glass substrate on which an indium oxide transparent electrode is provided, and rubbing treatment is performed in a certain direction so that glass fibers (so that the rubbing directions of the two substrates are parallel). A liquid crystal cell was assembled with the diameter of 5 μm) as a spacer, and the above-mentioned liquid crystal composition was vacuum-sealed in this to obtain a liquid crystal element. When this liquid crystal element was combined with a deflector and an electric field of 20 V was applied, a change in transmitted light intensity was observed. Table 13 shows the spontaneous polarization values (by the Sawyer-Toyer method) at this time. Table 13 shows the phase series of the liquid crystal composition. As is clear from these results, the optically active aromatic compound [1] having a trifluoromethyl group of the present invention can be driven in a room temperature region by forming a liquid crystal composition even if the compound itself does not show a Sc * phase. It became a ferroelectric liquid crystal material, and it was found that the liquid crystal material had induced spontaneous polarization required for high-speed response. Examples 63 to 82 Of the optically active aromatic compounds having a trifluoromethyl group [1] of the present invention, Table-14 showing a Sc * phase alone.
The liquid crystal element was manufactured using the compound simple substance described in 1 above according to the above-mentioned liquid crystal element manufacturing method, and the spontaneous polarization value was measured. The results are shown in Table-14. Examples 83 to 104 Of the liquid crystal elements obtained in Examples 58 to 82, the liquid crystal elements described in Table 15 were combined with a deflector, and the thickness of the liquid crystal element was 1 μm.
When an electric field of 10 V was applied, a change in transmitted light intensity was observed. The response time was measured from the change in transmitted light intensity at this time. The results are shown in Table-15. As is clear from the results, it was confirmed that the liquid crystal material of the present invention had excellent high-speed response.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 69/63 C07C 69/63 69/708 69/708 Z 69/88 69/88 69/92 69/92 69/94 69 / 94 C07D 239/26 C07D 239/26 239/28 239/28 239/34 239/34 C09K 19/20 C09K 19/20 19/34 19/34 G02F 1/13 500 G02F 1/13 500 (72) Inventor Masayoshi Minami 2-10-1 Tsukahara, Takatsuki City, Osaka Prefecture, Japan Sumitomo Chemical Industries Co., Ltd. Kitahara 6 Sumitomo Chemical Co., Ltd. (72) Inventor Koichi Fujisawa 6 Kitahara, Tsukuba City, Ibaraki Prefecture Sumitomo Chemical Co., Ltd. (56) References JP-A-3-31238 (JP, A) JP-A-3-3 31243 (JP, A) (58) Field surveyed (Int. Cl. ⁶ , DB name) CA (STN) REGISTRY (STN)

Claims (7)

(57) [Claims] (1) General formula (Wherein, R ¹ represents an alkyl group having 3 to 20 carbon atoms, and R ² represents an alkyl group or an alkoxyalkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom. K is 0 or 1 And n represents an integer of 0 to 5, and p represents 0 or 1.
Is shown. Ar is Or Is shown. Y represents -O-, -COO- or -OCO-. X
Represents -COO- when n is 0, and -COO- or -OCO- when n is an integer of 1 to 5. * Indicates an asymmetric carbon atom. An optically active aromatic compound having a trifluoromethyl group represented by the formula: 2. The general formula (In the formula, R ² , n, p and * mark have the same meanings as described above.) 3. A compound represented by the formula: R ¹ Y _k Ar—COR ′ (wherein R ¹ , k, Ar and Y have the same meanings as described above;
R 'represents a hydroxyl group or a halogen atom. Wherein the carboxylic acid compound represented by the formula (1) is reacted with the optically active phenol derivative according to the above (2), wherein X is -COO. A method for producing a compound, 4. General formula (Wherein, R ² , R ′, p and * have the same meanings as described above, and n ′ represents an integer of 1 to 5). 5. The phenolic compound represented by the general formula R ¹ Y _k Ar-OH (wherein R ¹ , k, Ar and Y have the same meanings as described above) and the optically active benzoic acid according to claim 4. The method for producing a compound wherein X is -OCO- among the optically active aromatic compounds having a trifluoromethyl group according to claim 1, wherein the compound is reacted with an acid derivative. 6. A liquid crystal composition comprising at least one optically active aromatic compound having a trifluoromethyl group according to claim 1 as a compounding component. 7. A liquid crystal device comprising a liquid crystal composition containing at least one optically active aromatic compound having a trifluoromethyl group according to claim 1 as a compounding component.