JPS61205227A - Fluorine-containing hydroxy-c-alkanone and production thereof - Google Patents
Fluorine-containing hydroxy-c-alkanone and production thereofInfo
- Publication number
- JPS61205227A JPS61205227A JP4682685A JP4682685A JPS61205227A JP S61205227 A JPS61205227 A JP S61205227A JP 4682685 A JP4682685 A JP 4682685A JP 4682685 A JP4682685 A JP 4682685A JP S61205227 A JPS61205227 A JP S61205227A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- alkanone
- formula
- hydroxy
- yeast
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 26
- 239000011737 fluorine Substances 0.000 title claims abstract description 25
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 8
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000013543 active substance Substances 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 241000183024 Populus tremula Species 0.000 abstract 2
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000006162 fluoroaliphatic group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- -1 6-hydroxy- 2-trifluoromethyl-1-hexen-3-one Chemical compound 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
イ、産業上の利用分野
本発明は含フッ素ヒドロキシ−Ｃ−アルカノン及びその
製造方法に関するもの。DETAILED DESCRIPTION OF THE INVENTION A. Field of Industrial Application The present invention relates to a fluorine-containing hydroxy-C-alkanone and a method for producing the same.
解されることのないハロゲン含有化合物の微生物学的挙
動に感心が寄せられている。There is interest in the microbiological behavior of halogen-containing compounds, which remains largely unknown.
本出願人は、特願昭５７−１５１０１０号において既に
、次式に示す如くにして含フッ素カルボニル化合物を活
性なパン酵母によって不斉還元し、立体構造のコントロ
ール下に含フッ素アルコールを微生物学的に得る方法を
提案した。The present applicant has already reported in Japanese Patent Application No. 151010/1987 that a fluorine-containing carbonyl compound is asymmetrically reduced using active baker's yeast as shown in the following formula, and a fluorine-containing alcohol is microbiologically reduced under the control of the steric structure. proposed a method to obtain it.
ＲｊＣ（０） ＲＲ７ＲｊＣＨ（ＯＨ） Ｒ（但し、Ｒ
ｌｆはペルフルオロアルキル基、Ｒはアルキル基又はＣ
Ｈｚ ＣＯｚ Ｅ を等）更にまた、フッ素化学につい
ての最近の文献によれば、含フッ素生物活性分子の不斉
合成に有用なキラルな合成手段が注目されている。（Ｇ
、Ｂ。RjC(0) RR7RjCH(OH) R (However, R
lf is a perfluoroalkyl group, R is an alkyl group or C
Furthermore, recent literature on fluorine chemistry has focused on chiral synthetic means useful for the asymmetric synthesis of fluorine-containing bioactive molecules. (G
,B.
Ｑｕｉｓｔａｄ、 Ｄ、 Ｃ，Ｃｅｒｆ 、 Ｄ、
Ａ、 ５ｃｈｏｏｌｅｙ＋ａｎｄ Ｇ、 Ｂ、 ５ｔａ
ａＬ Ｎａｔｕｒｅ＋ ２８９． １７６（１９８１）
等）。Quistad, D., C., Cerf, D.
A, 5chooley+and G, B, 5ta
aL Nature+ 289. 176 (1981)
etc).
ハ、発明の目的
本発明の目的は、所定位置にフッ素原子を有する新規で
有用な環状化合物を提供することにある。C. OBJECT OF THE INVENTION An object of the present invention is to provide a novel and useful cyclic compound having a fluorine atom at a predetermined position.
本発明の他の目的は、上記の如く生物化学的手法がフッ
素化学における光学活性体を得るための合成手段となり
得ることに留意し、微生物変換による不斉誘導を伴う環
化反応によって上記環状化合物を効果的に得ることので
きる方法を提供することにある。Another object of the present invention is to synthesize the above-mentioned cyclic compounds by a cyclization reaction accompanied by asymmetric induction by microbial conversion, keeping in mind that biochemical techniques can be used as a synthetic means for obtaining optically active substances in fluorine chemistry as described above. The goal is to provide a method that can effectively obtain the following.
二、発明の構成及びその作用効果
即ち、本発明は、
一般式：
（但し、Ｒ１及びＲ２の一方は含フッ
素脂肪族基であり、他方は水素原子
である。ｎは５以下、好ましくは３
以下の整数である。）
で表わされる含フッ素ヒドロキシ−Ｃ−アルカノンに係
るものである。2. Structure of the invention and its effects, that is, the present invention has the general formula: (However, one of R1 and R2 is a fluorine-containing aliphatic group, and the other is a hydrogen atom. n is 5 or less, preferably 3 (The following integer.) This relates to a fluorine-containing hydroxy-C-alkanone represented by:
本発明のこのアルカノンは分子内の所定位置フルオロ脂
肪族基（Ｒ１又はＲ２）を有し、特にこのフルオロ脂肪
族基及びＯ）１基の結合した炭素原子がキラルであるた
め、優れた生理活性作用、例えば抗炎症剤や抗生物質の
半合成中間体としての効能を発揮することのできるもの
である。This alkanone of the present invention has a fluoroaliphatic group (R1 or R2) at a predetermined position within the molecule, and in particular, since the carbon atom to which this fluoroaliphatic group and O)1 group are bonded is chiral, it has excellent physiological activity. For example, it can exhibit efficacy as a semi-synthetic intermediate for anti-inflammatory agents and antibiotics.
本発明の上記アルカノンの一般式中、上記フルオロ脂肪
族基（Ｒ１又はＲ２）は、特に炭素原子数ｌＯ以下の低
級フルオロアルキル基（Ｒｆ）であるのがよいが、こう
したＲｊ （特にペルフルオロアルキル基）は、一般
式：ＣＦａ （ＣＦ２）ｎ−又は（ＣＦａ）２ＣＦ
（ＣＦ２）ｎ−で表わされるもの、例えばＣＦ３−１Ｃ
Ｆ３ＣＦ２−１ＣＦ３ （ＣＦｚ）２−１ＣＦ３ （Ｃ
Ｆ２） ３−１ＣＦａ （ＣＦ２）４−１ＣＦ３
（ＣＦ２）ｓ−１ＣＦ３ （ＣＦｚ）ｓ−１（ＣＦ３）
ｚＣＦ−１（ＣＦａ）２ＣＦＣＦ２−１（ＣＦ３）２Ｃ
Ｆ （ＣＦ２）２−１（ＣＦａ）ｚＣＦ （ＣＦ２）ａ
−等がある。これら以外に、Ｒｊとして含フッ素アルケ
ニル基、例えばＣＦ２塩ＣＦＣＦ２−１ＣＦａＣＦ−Ｃ
Ｆ一本発明はまた、上記アルカノンを効果的に得るため
に、
一般式：
（但し、Ｒ１及びＲ２の一方は上記し
た含フッ素脂肪族基であり、他方は
水素原子である。ｎは５以下、好ま
しくは３以下の整数である。）
で表わされる含フッ素不飽和アルコールに酵母を作用さ
せて、
一般式：
（但し、Ｒ１、Ｒ２及びｎは前記した
ものと同じである。）
で表わされる含フッ素ヒドロキシ−〇−アルカノンを得
る含フッ素ヒドロキシ−Ｃ−アルカノンの製造方法も提
供するものである。In the general formula of the alkanone of the present invention, the fluoroaliphatic group (R1 or R2) is preferably a lower fluoroalkyl group (Rf) having 10 or less carbon atoms. ) has the general formula: CFa (CF2)n- or (CFa)2CF
(CF2) Those represented by n-, such as CF3-1C
F3CF2-1CF3 (CFz)2-1CF3 (C
F2) 3-1CFa (CF2)4-1CF3
(CF2)s-1CF3 (CFz)s-1(CF3)
zCF-1(CFa)2CFCF2-1(CF3)2C
F (CF2)2-1(CFa)zCF (CF2)a
- etc. In addition to these, Rj is a fluorine-containing alkenyl group, such as CF2 salt CFCF2-1CFaCF-C
F1 The present invention also provides, in order to effectively obtain the above alkanone, general formula: (However, one of R1 and R2 is the above-mentioned fluorine-containing aliphatic group, and the other is a hydrogen atom. , preferably an integer of 3 or less) is treated with yeast to form a fluorine-containing unsaturated alcohol represented by the general formula: (However, R1, R2, and n are the same as described above.) The present invention also provides a method for producing a fluorine-containing hydroxy-C-alkanone to obtain a fluorine-containing hydroxy-C-alkanone.
本発明の製造方法は特に、ｐＨ４〜７．５の弱酸性下（
望ましく ｃＷ ｐ ）１５．５〜６．０）で実施する
のが、不要な他の反応を生起せしめない点で望ましい。The production method of the present invention is particularly suitable for use under weakly acidic conditions of pH 4 to 7.5 (
It is preferable to carry out the reaction at a cW p ) of 15.5 to 6.0) in order to avoid causing other unnecessary reactions.
また、反応温度も酵母の作用を効率良く生ぜしめる上で
２５〜４０℃とするのがより、３５〜３７℃とするのが
最適である。Further, the reaction temperature is preferably 25 to 40°C, and more preferably 35 to 37°C, in order to efficiently produce the action of yeast.
他の反応条件としては、溶媒は水でよく、反応時間は数
日〜１週間程度であるのがよい。As for other reaction conditions, the solvent may be water, and the reaction time is preferably about several days to one week.
次に本発明を反応式に従ってより詳細に説明す ・る。Next, the present invention will be explained in more detail according to the reaction formula.
まず、微生物によるマイケル付加反応を分子内環化反応
に利用するため、ω″−ヒドロキシーαはβ−フルオロ
アルキル−α、β−不飽和ケトン頬１を公知の方法に従
って次の如くに合成する。First, in order to utilize the Michael addition reaction by a microorganism for an intramolecular cyclization reaction, ω''-hydroxy-α, β-fluoroalkyl-α, and β-unsaturated ketone 1 are synthesized as follows according to a known method.
〜
Ｒｆ ＣＨＯ＋ＢｒＣＨｚＣＯｚＥｔ
Ｃｕｌ／ＴＨＦ ＩＱ／ヘス７＼ΔＴｓこの反応に
おいて、超音波照射は、Ｎ、 ＩａｈｉｋａｗａＭ、
Ｇ、 Ｋｏｈ、 Ｔ、 Ｋｉｔａｚｕｍｅ 、 Ｓ、
Ｋ、 ＣｈｏｉによるＪ 、 Ｆ １ｕｏｒｉｎｅ
Ｃｈｅｗ、、 Ｊ、−土、４１９（１９８４）による。~ Rf CHO+BrCHzCOzEt Cul/THF IQ/Hess7\ΔTs In this reaction, the ultrasound irradiation is performed using N, IahikawaM,
G., Koh, T., Kitazume, S.
J, F 1uorine by K, Choi
Chew, J.-Sat., 419 (1984).
この超音波照射は行わなくてもよい。なお、上記におい
て、ＴＨＦはテトラＴ ｓ ｏ／＼／ Ｍ ｇ Ｂ ｒ
を用いてもよい。This ultrasonic irradiation may not be performed. In addition, in the above, THF is tetraTso/\/MgBr
may also be used.
そして、このω−ヒドロキシ体１を下記の如（に分子内
不斉環化反応させる際にパン酵母を用いる発酵法を通用
子８るが、例えばまず３日間発酵させたのち、更にパン
酵母を加えて４日間反応させる。Then, a fermentation method using baker's yeast is used to subject this ω-hydroxy compound 1 to an intramolecular asymmetric cyclization reaction as described below. In addition, the mixture was allowed to react for 4 days.
１ ２（ｎ雷ｌ又は２）一覧Ｉ−
−ノ
こうして生成物であるキラル（光学活性）な３−フルオ
ロアルキル−４−ヒドロキシ−ｃ−１−アルカノン２（
＊はキラル炭素を示す。）を得〜
るが、この際、系のｐＨを特に５．５〜８．０に保つこ
とが好ましい。何故ならば分子内にはカルボニル基や二
重結合といった官能基が存在し、これらが酵素の作用に
よって他の変換を受けて副生成物が生じ得るからである
。1 2 (n thunder l or 2) list I-
-Thus, the product chiral (optically active) 3-fluoroalkyl-4-hydroxy-c-1-alkanone 2(
* indicates chiral carbon. ), but at this time, it is preferable to keep the pH of the system particularly between 5.5 and 8.0. This is because functional groups such as carbonyl groups and double bonds are present in the molecule, and these can undergo other conversions by the action of enzymes to produce by-products.
また、別のω−ヒドロキシ体３から次式の如く、上記と
同様にしてキラルな２−フルオロ・アルキル−４−ヒド
ロキシ−ｃ−１−アルカノン４を得ることができる。Furthermore, chiral 2-fluoro alkyl-4-hydroxy-c-1-alkanone 4 can be obtained from another ω-hydroxy compound 3 as shown in the following formula in the same manner as above.
３４（ｎ−１又は２）
〜
〜生成物２又は４の立体化学的知見は１９ＦＮＭＲ
〜 〜
により得ることができ、下記表−１に示すように高いジ
アステレオ選択性で高収率に得られることが分かる。34 (n-1 or 2) ~
~ Stereochemical findings of products 2 or 4 are based on 19F NMR
~ ~ As shown in Table 1 below, it can be seen that it can be obtained with high diastereoselectivity and high yield.
Ｈ
Ｈｆ
Ｈ
Ｈ
ら確認。これらの新規な化合物の微量分析結果は計算値
と充分に一致していた
（Ｃ，Ｈ，Ｎ±０．５％）
ｂ）’ＦＮＭＲのシグナル強度比により決定。Confirmed by H Hf H H et al. The trace analysis results of these new compounds were in good agreement with the calculated values (C, H, N ± 0.5%) b) 'Determined by FNMR signal intensity ratio.
ホ、実施例 以下、本発明を実施例について更に詳細に説明する。E, Example Hereinafter, the present invention will be explained in more detail with reference to Examples.
皇施劇上
１．２１の緩衝溶１ （ｐＨ５，９： １／１５Ｍ
Ｎａ ２ＨＰＯ４溶液（１２０ｎｌ）と１／１５Ｍ
ＫＨ２ＰＯ４溶液□’ （１０８０ｍ ｌ！ ）より
調整〕にパン酵母（オリエンタル社製） １００ｇと
デンプン粉１５０ｇを入れ、ジャーファーメンタ−（Ｍ
−１００、東京理化機器製）中、３５−３６℃に温度を
保ち、１時間攪拌した。この溶液に、６−ヒドロキシ−
２−トリフルオロメチル−１−ヘキセン−３−オン（３
，７ｇ 、 ２０ ｍｍｏｊり母（５０ｇ ）とデンプ
ン粉（７５ｇ ）を溶液に加え、３５〜３６℃に温度を
保って４日間攪拌した。Buffer solution 1 (pH 5,9: 1/15M)
Na2HPO4 solution (120nl) and 1/15M
Add 100 g of baker's yeast (manufactured by Oriental) and 150 g of starch powder to KH2PO4 solution □' (1080 ml!),
-100 manufactured by Tokyo Rikakiki Co., Ltd.), the temperature was maintained at 35-36°C and stirred for 1 hour. Add 6-hydroxy-
2-trifluoromethyl-1-hexen-3-one (3
, 7g, 20mmOj mother (50g) and starch powder (75g) were added to the solution and stirred for 4 days while maintaining the temperature at 35-36°C.
反応後、凝集剤（Ｐ−７１３、第一工業製薬社製、２０
０ ｒＰｗｓの溶液２００ｍ ｌ！ ）を溶液に加え、
１時間静置した後、酢酸エチルで有機物を抽出し、抽出
液を無水硫酸マグネシウムで乾燥した。溶媒を留去した
のち、減圧蒸留により生成物を得た。分析データは次の
通りであ□った。After the reaction, a flocculant (P-713, manufactured by Daiichi Kogyo Seiyaku Co., Ltd., 20
200 ml of solution of 0 rPws! ) to the solution,
After standing for 1 hour, organic matter was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. After distilling off the solvent, a product was obtained by distillation under reduced pressure. The analysis data were as follows.
”ＦＮＭＲ（ＣＤＣＪ１３）：δ１．２ （ｍ、 １
１”ＣＦ ３−’ＨＮＭＲ（ＣＤ Ｃｌ ａ ） 、：
δ １．６〜２．４ （６Ｈ）、４．３１ （ｍ、
Ｉ Ｈ） 、４．０２ （ｍ、 Ｉ Ｈ）
。"FNMR (CDCJ13): δ1.2 (m, 1
1"CF3-'HNMR (CDCla):
δ 1.6-2.4 (6H), 4.31 (m,
IH), 4.02 (m, IH)
.
放物を得た。I got a paraboloid.
″′ Ｉｌｌ
臨 Ｎ−り
ゆ−工
エ″' Ill Rin N-ri
Yukoe
Claims (1)
あり、他方は水素原子である、ｎは５以下の整数である
。） で表わされる含フッ素ヒドロキシ−ｃ−アルカノン。 ２、Ｒ＾１及びＲ＾２の一方が炭素原子数１０以下の含
フッ素アルキル又はアルケニル基である、特許請求の範
囲の第１項に記載したアルカノン。 ３、光学活性のある、特許請求の範囲の第１項に記載し
たアルカノン。 ４、一般式： ▲数式、化学式、表等があります▼ （但し、Ｒ＾１及びＲ＾２の一方は含フッ素脂肪族基で
あり、他方は水素原子である、ｎは５以下の整数である
。） で表わされる含フッ素不飽和アルコールに酵母を作用さ
せて、 一般式： ▲数式、化学式、表等があります▼ （但し、Ｒ＾１、Ｒ＾２及びｎは前記したものと同じで
ある。） で表わされる含フッ素ヒドロキシ−ｃ−アルカノンを得
る含フッ素ヒドロキシ−ｃ−アルカノンの製造方法。 ５、ｐＨ４〜７．５の条件下でパン酵母を作用させる、
特許請求の範囲の第４項に記載した方法。 ６、Ｒ＾１及びＲ＾２の一方が炭素原子数１０以下の含
フッ素アルキル又はアルケニル基である、特許請求の範
囲の第４項に記載した方法。[Claims] 1. General formula: ▲ Numerical formula, chemical formula, table, etc.▼ (However, one of R^1 and R^2 is a fluorine-containing aliphatic group, the other is a hydrogen atom, n is an integer of 5 or less.) A fluorine-containing hydroxy-c-alkanone represented by: 2. The alkanone according to claim 1, wherein one of R^1 and R^2 is a fluorine-containing alkyl or alkenyl group having 10 or less carbon atoms. 3. An optically active alkanone as described in claim 1. 4. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, one of R^1 and R^2 is a fluorine-containing aliphatic group, the other is a hydrogen atom, and n is an integer of 5 or less. ) The fluorinated unsaturated alcohol represented by A method for producing a fluorine-containing hydroxy-c-alkanone to obtain a fluorine-containing hydroxy-c-alkanone represented by 5. Let baker's yeast act under conditions of pH 4 to 7.5.
A method according to claim 4. 6. The method according to claim 4, wherein one of R^1 and R^2 is a fluorine-containing alkyl or alkenyl group having 10 or less carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4682685A JPS61205227A (en) | 1985-03-09 | 1985-03-09 | Fluorine-containing hydroxy-c-alkanone and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4682685A JPS61205227A (en) | 1985-03-09 | 1985-03-09 | Fluorine-containing hydroxy-c-alkanone and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61205227A true JPS61205227A (en) | 1986-09-11 |
Family
ID=12758130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4682685A Pending JPS61205227A (en) | 1985-03-09 | 1985-03-09 | Fluorine-containing hydroxy-c-alkanone and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205227A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003100529A (en) * | 2001-09-27 | 2003-04-04 | Daihen Corp | On-load tap changing device |
-
1985
- 1985-03-09 JP JP4682685A patent/JPS61205227A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003100529A (en) * | 2001-09-27 | 2003-04-04 | Daihen Corp | On-load tap changing device |
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