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DE4432970A1 - New tetra:cyclic cpds., e.g. cyclo:alkyl:phenanthrene derivs. - Google Patents

New tetra:cyclic cpds., e.g. cyclo:alkyl:phenanthrene derivs.

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DE4432970A1
DE4432970A1 DE4432970A DE4432970A DE4432970A1 DE 4432970 A1 DE4432970 A1 DE 4432970A1 DE 4432970 A DE4432970 A DE 4432970A DE 4432970 A DE4432970 A DE 4432970A DE 4432970 A1 DE4432970 A1 DE 4432970A1
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cyclopenta
dihydro
phenanthrene
dioxole
aza
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Rainer Dr Wingen
Javier Dr Manero
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Aventis Research and Technologies GmbH and Co KG
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Hoechst AG
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Abstract

Tetracyclic cpds. of formula (I) are new. (where, R1 = H, CN, F, Cl, CF3, or 1-20C alkyl which may have (a) one or more CH2 gps. replaced by O, S, CO, CH=CH, ethynylene, cyclopropylene, SiMe2, 1,4-phenylene, 1,4-cyclohexylene, 1,3-cyclopentylene or 1,3-cyclobutylene, provided that O and S atoms are non adjacent, and/or (b) one of more H atoms replaced by F, Cl, Br or OR3 or by a gp. of the following formula: Q = Cl, F, CN or Me; R2 = H, or 1-20C alkyl which may have (a) one or more CH2 gps. replaced by O, S, CO, CH=CH, ethynylene, cyclopropylene, SiMe2, 1,4-phenylene, 1,4-cyclohexylene, 1,3-cyclopentylene, 1,3-cyclobutylene or 1,3-dioxane-2,5-diyl, provided that O and S atoms are non-adjacent, and/or (b) one of more H atoms replaced by F,Cl, Br or OR3; R3 = H or 1-6C alkyl; R4-R6 = H, or 1-16C alkyl with may have 1-2 CH2 gps. replaced by O and/or CH=CH, provided that O atoms are non-adjacent, or R4+R5 may form a (CH2)4 or (CH2)5 gp. when bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyran, butyrolactone or valerolactone ring; A1 = 1,4=phenylene (opt. substd. by 1-3 F atoms), 1,4-cyclohexylene, pyridine-2,5-diyl, 6-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl or 1,3,4-thiadiazole-2,5-diyl; M1 = a bond, CH2CH2, ethynylene, OCO, COO, OCH2, CH2O or OCOO; m = 0 or 1; A = a ring of the following formulae: C = a ring of the following formulae: D = a ring of the following formulae: B1 and B2 = CH=CH, CH=N, N=CH, CH2CH2, CH2O, OCH2, OCO or COO; k and n = 0 or 1, provided that k+n = 1).

Description

Neben nematischen und cholesterischen Flüssigkristallen werden in jüngerer Zeit auch optisch aktive geneigt smektische (ferroelektrische) Flüssigkristalle in kommerziellen Displayvorrichtungen verwendet.In addition to nematic and cholesteric liquid crystals, more recently also optically active inclined smectic (ferroelectric) liquid crystals in commercial display devices used.

Clark und Lagerwall konnten zeigen, daß der Einsatz ferroelektrischer Flüssigkristalle (FLC) in sehr dünnen Zellen zu optoelektrischen Schalt- oder Anzeigeelementen führt, die im Vergleich zu den herkömmlichen TN ("twisted nematic")-Zellen um bis zu einem Faktor 1000 schnellere Schaltzeiten haben (siehe z. B. EP-A 0 032 362). Aufgrund dieser und anderer günstiger Eigenschaften, z. B. der bistabilen Schaltmöglichkeit und des nahezu blickwinkelunabhängigen Kontrasts, sind FLCs grundsätzlich für Anwendungsgebiete wie Computerdisplays gut geeignet.Clark and Lagerwall were able to show that the use of ferroelectric Liquid crystals (FLC) in very thin cells for optoelectric switching or Display elements leads, which compared to the conventional TN ("twisted nematic ") cells have switching times that are up to a factor of 1000 faster (see e.g. EP-A 0 032 362). Because of this and others cheaper Properties, e.g. B. the bistable switching option and almost angle-independent contrast, FLCs are basically for Areas of application such as computer displays are well suited.

Für die Verwendung von FLCs in elektrooptischen oder vollständig optischen Bauelementen benötigt man entweder Verbindungen, die geneigte bzw. orthogonale smektische Phasen ausbilden und selbst optisch aktiv sind, oder man kann durch Dotierung von Verbindungen, die zwar solche smektischen Phasen ausbilden, selbst aber nicht optisch aktiv sind, mit optisch aktiven Verbindungen ferroelektrische smektische Phasen induzieren. Die gewünschte Phase soll dabei über einen möglichst großen Temperaturbereich stabil sein.For the use of FLCs in electro-optical or completely optical Components either require connections that are inclined or form orthogonal smectic phases and are themselves optically active, or one can by doping compounds that are smectic Form phases, but are not optically active themselves, with optically active ones Compounds induce ferroelectric smectic phases. The desired The phase should be stable over the largest possible temperature range.

Zur Erzielung eines guten Kontrastverhältnisses in elektrooptischen Bauelementen ist eine einheitliche planare Orientierung der Flüssigkristalle nötig. To achieve a good contrast ratio in electro-optical Components require a uniform planar orientation of the liquid crystals.  

Eine gute Orientierung in der SA- und S*C-Phase läßt sich erreichen, wenn die Phasenfolge der Flüssigkristallmischung mit abnehmender Temperatur lautet:A good orientation in the S A and S * C phase can be achieved if the phase sequence of the liquid crystal mixture with decreasing temperature is:

Isotrop → N* → SA → S*C Isotropic → N * → S A → S * C

Voraussetzung ist, daß der Pitch (Ganghöhe der Helix) in der N*-Phase sehr groß (größer 10 µm) oder, noch besser, völlig kompensiert ist (siehe z. B. T. Matsumoto et al, Proc. of the 6th Int. Display Research Conf., Japan Display, Sept. 30 bis Okt. 2, 1986, Tokyo, p. 468-470; M. Murakami et al, ibid. S. 344 bis S. 347). Dies erreicht man, indem man zu der chiralen Flüssigkristallmischung, die in der N*-Phase z. B. eine linksdrehende Helix aufweist, einen weiteren optisch aktiven Dotierstoff, der eine rechtsdrehende Helix induziert, in solchen Mengen hinzugibt, daß die Helix gerade kompensiert wird.The prerequisite is that the pitch (pitch of the helix) is very large in the N * phase (larger than 10 µm) or, even better, completely compensated (see e.g. T. Matsumoto et al, Proc. of the 6th Int. Display Research Conf., Japan Display, Sept. 30 to Oct. 2, 1986, Tokyo, p. 468-470; M. Murakami et al, ibid. P. 344 to p. 347). This is accomplished by going to the chiral Liquid crystal mixture which in the N * phase z. B. a left-turning helix has a further optically active dopant that has a clockwise rotation Helix induces in such amounts that the helix just compensates becomes.

Für die Verwendung des SSFLCD-Effektes (Surface Stabilized Ferroelectric Liquid Crystal Display) von Clark und Lagerwall zur einheitlichen, planaren Orientierung ist ferner Voraussetzung, daß der Pitch in der smektischen C*- Phase wesentlich größer ist als die Dicke des Anzeigeelementes (Mol. Cryst. Liq. Cryst. 1983, 94, 213-134 und 1984, 114, 151-187). Dies erreicht man wie im Fall des cholesterischen Pitches durch Verwendung von Dotierstoffen mit entgegengesetztem Drehsinn der Helix.For the use of the SSFLCD effect (Surface Stabilized Ferroelectric Liquid Crystal Display) from Clark and Lagerwall for uniform, planar Orientation is also a prerequisite that the pitch in the smectic C * - Phase is significantly greater than the thickness of the display element (Mol. Cryst. Liq. Cryst. 1983, 94, 213-134 and 1984, 114, 151-187). This is achieved like in the Case of cholesteric pitch using dopants with opposite direction of rotation of the helix.

Ferroelektrische Flüssigkristallanzeigen lassen sich auch durch Nutzung des DHF (Distorted Helix Formation)-Effektes oder des PSFLCD-Effektes (Pitch Stabilized Ferroelectric Liquid Crystal Display, auch SBF = Short pitch Bistable Ferroelektric Effekt genannt) betreiben. Der DHF-Effekt wurde von B. I. Ostrovski in Advances in Liquid Crystal Research and Applications, Oxford/Budapest, 1980, 469 beschrieben; der PSFLCD-Effekt ist in DE-A 39 20 625 bzw. EP-A 0 405 346 beschrieben. Zur Nutzung dieser Effekte wird im Gegensatz zum SSFLCD-Effekt ein flüssigkristallines Material mit einem kurzen SC-Pitch benötigt. Ferroelectric liquid crystal displays can also be operated by using the DHF (Distorted Helix Formation) effect or the PSFLCD effect (Pitch Stabilized Ferroelectric Liquid Crystal Display, also called SBF = Short pitch Bistable Ferroelectric Effect). The DHF effect was described by BI Ostrovski in Advances in Liquid Crystal Research and Applications, Oxford / Budapest, 1980, 469; the PSFLCD effect is described in DE-A 39 20 625 and EP-A 0 405 346. In contrast to the SSFLCD effect, a liquid crystal material with a short S C pitch is required to use these effects.

Die optische Schaltzeit T [µs] ferroelektrischer Flüssigkristallsysteme, die möglichst kurz sein soll, hängt von der Rotationsviskosität des Systems γ [mPa·s], der spontanen Polarisation PS [nC/cm²] und der elektrischen Feldstärke E [V/m] ab nach der BeziehungThe optical switching time T [µs] of ferroelectric liquid crystal systems, which should be as short as possible, depends on the rotational viscosity of the system γ [mPa · s], the spontaneous polarization P S [nC / cm²] and the electric field strength E [V / m] after the relationship

Da die Feldstärke E durch den Elektrodenabstand im elektrooptischen Bauteil und durch die angelegte Spannung festgelegt ist, muß das ferroelektrische Anzeigemedium niedrigviskos sein und eine hohe spontane Polarisation aufweisen, damit eine kurze Schaltzeit erreicht wird.Since the field strength E is due to the electrode spacing in the electro-optical component and is determined by the applied voltage, the ferroelectric Display medium be low viscosity and high spontaneous polarization have so that a short switching time is achieved.

Schließlich wird neben thermischer, chemischer und photochemischer Stabilität eine kleine optische Anisotropie Δn, vorzugsweise ≈ 0,13, und eine geringe positive oder vorzugsweise negative dielektrische Anisotropie Δ ∈ verlangt (siehe S.T. Lagerwall et al, "Ferroelectric Liquid Crystal for Displays" SID Symposium, Oct. Meeting 1985, San Diego, Ca. USA).Finally, in addition to thermal, chemical and photochemical stability a small optical anisotropy Δn, preferably ≈ 0.13, and a small one requires positive or preferably negative dielectric anisotropy Δ ∈ (see S.T. Lagerwall et al, "Ferroelectric Liquid Crystal for Displays" SID Symposium, Oct. Meeting 1985, San Diego, Ca. USA).

Die Gesamtheit dieser Forderungen ist nur mit Mischungen aus mehreren Komponenten zu erfüllen. Als Basis (oder Matrix) dienen dabei bevorzugt Verbindungen, die möglichst selbst bereits die gewünschte Phasenfolge I → N → SA → SC aufweisen. Weitere Komponenten der Mischung werden oftmals zur Schmelzpunktserniedrigung und zur Verbreiterung der SC- und meist auch N-Phase, zum Induzieren der optischen Aktivität, zur Pitch-Komponsation und zur Anpassung der optischen und dielektrischen Anisotropie zugesetzt, wobei aber beispielsweise die Rotationsviskosität möglichst nicht vergrößert werden soll.All of these requirements can only be met with mixtures of several components. The basis (or matrix) used is preferably compounds which, if possible, already have the desired phase sequence I → N → S A → S C. Other components of the mixture are often added to lower the melting point and broaden the S C - and usually also the N phase, to induce optical activity, to pitch composition and to adapt the optical and dielectric anisotropy, but, for example, do not increase the rotational viscosity if possible shall be.

Derivate des Phenanthrens (wozu hier auch 9,10-Dihydrophenanthrene gezählt werden) wurden bereits als Flüssigkristalle bzw. als Komponenten flüssigkristalliner Mischungen beschrieben:
Azomethine mit einer Phenanthren- bzw. 9,10-Dihydrophenanthren-Einheit (J. Chem. Soc. [London] 1958, 552; J. Chem. Soc., Perkin 11 1982, 465); Keto- Derivate des 9,10-Dihydrophenanthrens bzw. Phenanthrens (Chem. Ind. [London] 1974, 615; Prod. Int. Liq. Cryst. Conf. (1973) 397; Tetrahedron 181, 37, 2815) und Carboxyl-Derivate des 9,10-Dihydrophenanthrens (DD-WP 1 53 826).Derivatives of phenanthrene (which also includes 9,10-dihydrophenanthrenes) have already been described as liquid crystals or as components of liquid-crystalline mixtures:
Azomethines with a phenanthrene or 9,10-dihydrophenanthrene unit (J. Chem. Soc. [London] 1958, 552; J. Chem. Soc., Perkin 11 1982, 465); Keto derivatives of 9,10-dihydrophenanthrene or phenanthrene (Chem. Ind. [London] 1974, 615; Prod. Int. Liq. Cryst. Conf. (1973) 397; Tetrahedron 181, 37, 2815) and carboxyl derivatives of 9,10-dihydrophenanthrene (DD-WP 1 53 826).

Derivate der Indans (EP-A 546 338) sowie kondensierte 6-Ring-5-Ring- Verbindungen (EP-A 555 843) sind bereits als Komponenten flüssigkristalliner Mischungen beschrieben.Derivatives of indans (EP-A 546 338) and condensed 6-ring-5-ring Compounds (EP-A 555 843) are already more liquid crystalline as components Mixtures described.

Da jedoch die Entwicklung, insbesondere von ferroelektrischen Flüssigkristallmischungen, noch in keiner Weise als abgeschlossen betrachtet werden kann, sind die Hersteller von Displays nach wie vor an den unterschiedlichsten Komponenten für Mischungen interessiert. Dieses unter anderem auch deshalb, weil erst das Zusammenwirken der flüssigkristallinen Mischung mit den einzelnen Bauteilen der Anzeigevorrichtung bzw. der Zelle (z. B. der Orientierungsschicht) Rückschlüsse auf die Qualität auch der flüssigkristallinen Mischung zuläßt.However, since the development, especially of ferroelectric Liquid crystal mixtures, in no way considered complete the manufacturers of displays are still at the various components interested in mixtures. This under among other things because only the interaction of the liquid crystalline Mix with the individual components of the display device or the cell (e.g. the orientation layer) conclusions on the quality of the allows liquid crystalline mixture.

Aufgabe der vorliegenden Erfindung war es daher, neue Verbindungen bereitzustellen, die in flüssigkristallinen Mischungen geeignet sind, das Eigenschaftsprofil dieser Mischungen zu verbessern.The object of the present invention was therefore to create new compounds To provide, which are suitable in liquid crystalline mixtures, the To improve the property profile of these mixtures.

Es wurde nun überraschend gefunden, daß tetracyclische Verbindungen der Formel (I) in besonderer Weise zum Einsatz in Flüssigkristallmischungen geeignet sind. It has now surprisingly been found that tetracyclic compounds of Formula (I) is particularly suitable for use in liquid crystal mixtures are.  

Gegenstand der Erfindung sind daher Verbindungen der Formel (I):The invention therefore relates to compounds of the formula (I):

wobei die Symbole und Indizes folgende Bedeutungen haben:
R¹: ist H, CN, F, Cl, CF₃, ein geradkettiger oder verzweigter Alkylrest (mit oder ohne asymmetrisches C-Atom) mit 1 bis 20 C-Atomen, wobei auch eine oder mehrere CH₂-Gruppen durch -O-, -S-, -C(=O)-, -CH=CH-, -C-C-, Cyclopropan-1,2-diyl, -Si(CH₃)₂-, 1,4- Phenylen, 1,4-Cyclohexylen, 1,3-Cyclopentylen, 1,3-Cyclobutylen ersetzt sein können, mit der Maßgabe, daß Sauerstoffatome und/oder Schwefelatome nicht unmittelbar miteinander gebunden sein dürfen, und/oder wobei ein oder mehrere H-Atome des Alkylrestes durch -F, -Cl, -Br oder -OR³ substituiert sein können, oder auch eine der nachfolgenden Gruppen (optisch aktiv oder racemisch):where the symbols and indices have the following meanings:
R¹: is H, CN, F, Cl, CF₃, a straight-chain or branched alkyl radical (with or without an asymmetric carbon atom) with 1 to 20 carbon atoms, one or more CH₂ groups by -O-, -S -, -C (= O) -, -CH = CH-, -CC-, cyclopropane-1,2-diyl, -Si (CH₃) ₂-, 1,4-phenylene, 1,4-cyclohexylene, 1, 3-cyclopentylene, 1,3-cyclobutylene can be replaced, with the proviso that oxygen atoms and / or sulfur atoms must not be bonded directly to one another, and / or one or more H atoms of the alkyl radical being used by -F, -Cl, - Br or -OR³ can be substituted, or one of the following groups (optically active or racemic):

R²: ist H oder ein geradkettiger oder verzweigter Alkylrest mit 1 bis 20 C-Atomen (mit oder ohne asymmetrisches C-Atom), wobei auch eine oder mehrere CH₂-Gruppen (jedoch nicht die unmittelbar an den Ring D gebundene) durch -O-, -S-, -CH=CH-, -C-C-, Cyclopropan-1,2-diyl, -Si(CH₃)₂-, -C( = O)-, 1,4-Phenylen, 1,4- Cyclohexylen, 1,3-Cyclopentylen, 1,3-Cyclobutylen, 1,3-Dioxan- 2,5-diyl ersetzt sein können mit der Maßgabe, daß Sauerstoffatome und Schwefelatome nicht direkt miteinander verbunden sein dürfen, und/oder ein oder mehrere H-Atome des Alkylrestes durch -F, -Cl, -Br oder -OR³ substituiert sein können;
R³: ist H oder ein geradkettiger Alkylrest mit 1 bis 6 C-Atomen;
R⁴, R⁵, R⁶: sind gleich oder verschieden Wasserstoff oder ein geradkettiger oder verzweigter Alkylrest mit 1-16 C-Atomen, wobei auch eine oder zwei CH₂-Gruppen durch -O- und/oder -CH=CH- ersetzt sein können, mit der Maßgabe, daß Sauerstoffatome nicht unmittelbar miteinander gebunden sein dürfen, R⁴ und R⁵ können zusammen auch -(CH₂)₄- oder -(CH₂)₅- sein, wenn sie an ein Oxiran-, Dioxolan-, Tetrahydrofuran-, Tetrahydropyran-, Bytorolacton- oder Valerolacton-System gebunden sind;
A¹: ist (gegebenenfalls durch 1 bis 3 F-Atome substituiertes) 1,4- Phenylen, 1,4-Cyclohexylen, Pyridin-2,5-diyl (ggf. α zum N-Atom durch F substituiert), Pyrimidin-2,5-diyl oder (1,3,4)-Thiadiazol-2,5- diyl;
M¹: ist eine Einfachbindung, -CH₂CH₂-, -C-C-, -O-CO-, -CO-O-, -O-CH₂-, CH₂-O oder -O-CO-O-;
Q¹: ist -CO-O- oder -CH₂-O- oder eine Einfachbindung
m: Null oder Eins;
Ring A: istR²: is H or a straight-chain or branched alkyl radical having 1 to 20 C atoms (with or without an asymmetrical C atom), one or more CH 2 groups (but not the one directly bonded to the ring D) also being -O- , -S-, -CH = CH-, -CC-, cyclopropane-1,2-diyl, -Si (CH₃) ₂-, -C (= O) -, 1,4-phenylene, 1,4-cyclohexylene , 1,3-cyclopentylene, 1,3-cyclobutylene, 1,3-dioxane-2,5-diyl can be replaced with the proviso that oxygen atoms and sulfur atoms must not be directly connected to one another, and / or one or more H- Atoms of the alkyl radical can be substituted by -F, -Cl, -Br or -OR³;
R³: is H or a straight-chain alkyl radical with 1 to 6 C atoms;
R⁴, R⁵, R⁶: are identical or different hydrogen or a straight-chain or branched alkyl radical having 1-16 C atoms, where one or two CH₂ groups can be replaced by -O- and / or -CH = CH- with the proviso that oxygen atoms must not be bonded directly to one another, R⁴ and R⁵ together can also be - (CH₂) ₄- or - (CH₂) ₅- if they are an oxirane, dioxolane, tetrahydrofuran, tetrahydropyran, bytorolactone - or valerolactone system are bound;
A¹: is (optionally substituted by 1 to 3 F atoms) 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl (optionally α to the N atom by F), pyrimidine-2, 5-diyl or (1,3,4) thiadiazole-2,5-diyl;
M¹: is a single bond, -CH₂CH₂-, -CC-, -O-CO-, -CO-O-, -O-CH₂-, CH₂-O or -O-CO-O-;
Q¹: is -CO-O- or -CH₂-O- or a single bond
m: zero or one;
Ring A: is

Ring C: istRing C: is

Ring D: istRing D: is

B¹, B²: sind -CH=CH-, -CH=N-, -N=CH-, -CH₂CH₂-, -CH₂O-, -OCH₂-, -O-CO-, -CO-O;
k, n: sind Null oder 1;
mit der Maßgabe, daß die Summe aus k und n 1 sein muß.B¹, B²: are -CH = CH-, -CH = N-, -N = CH-, -CH₂CH₂-, -CH₂O-, -OCH₂-, -O-CO-, -CO-O;
k, n: are zero or 1;
with the proviso that the sum of k and n must be 1.

Bevorzugte Verbindungen der Formel (I) sind solche der Formel (Ia) (mit k = 1),Preferred compounds of the formula (I) are those of the formula (Ia) (with k = 1),

worin
Ring A:wherein
Ring A:

bedeutet und die übrigen Symbole und Indizes die in der Formel (I) angegebenen Bedeutungen haben.means and the other symbols and indices have the meanings given in the formula (I).

Darunter besonders bevorzugt werden die Verbindungen der Formeln (Ia1 bis Ia12):Among these, particular preference is given to the compounds of the formulas (Ia1 to Ia12):

Weitere bevorzugte Verbindungen der Formel (I) sind solche der Formel (Ib) (mit k = 1),Further preferred compounds of the formula (I) are those of the formula (Ib) (with k = 1),

worin
Ring A:wherein
Ring A:

bedeutet und die übrigen Symbole und Indizes die in Formel (I) angegebenen Bedeutungen haben.means and the other symbols and indices those specified in formula (I) Have meanings.

Darunter besonders bevorzugt sind die Verbindungen der Formeln (Ib1) bis (Ib12):Among these, the compounds of the formulas (Ib1) to are particularly preferred (Ib12):

Die Verbindungen der Formel (I) bilden im allgemeinen flüssigkristalline Mesophasen in einem für die elektrooptische Verwendung günstig gelegenen Temperaturbereich. Chemisch, thermisch und gegen Licht sind sie stabil.The compounds of formula (I) generally form liquid crystalline Mesophases in one conveniently located for electro-optical use Temperature range. They are stable chemically, thermally and against light.

Die Herstellung der erfindungsgemäßen Verbindungen erfolgt nach an sich literaturbekannten Methoden, wie sie in Standwerken zur Organischen Synthese, z. B. Houben-Weyl, Methoden der Organischen Chemie, Georg- Thieme-Verlag, Stuttgart, beschrieben werden.The compounds according to the invention are prepared per se methods known from the literature, such as those used in organic structures Synthesis, e.g. B. Houben-Weyl, Methods of Organic Chemistry, Georg- Thieme-Verlag, Stuttgart.

Die Ausgangsstoffe können gewünschtenfalls auch in situ gebildet werden, und zwar derart, daß man sie aus dem Reaktionsgemisch nicht isoliert, sondern sofort weiter zu den Verbindungen der Formel (I) umsetzt.If desired, the starting materials can also be formed in situ, and in such a way that they are not isolated from the reaction mixture, but rather immediately continues to react to the compounds of formula (I).

So sind in den Schemata 1 bis 7 Herstellverfahren für die Verbindungen der Formel (Ia) beispielhaft aufgeführt.Schemes 1 to 7 show manufacturing processes for the compounds of Formula (Ia) listed as an example.

Schema 1 zeigt, ausgehend von 1-Alkyloxy-6-ethinylpyridin, dessen Herstellung beispielsweise in der deutschen Patentanmeldung P 44 01 004.4 mit dem Titel "Phenanthren Derivate und ihre Verwendung in flüssigkristallinen Mischungen" beschrieben ist, beispielhaft die Synthese der bevorzugten Verbindungen (Ia1). Darin steht R für eine gegebenenfalls durch -O- oder -Si(CH₃)₂- substituierte Alkylgruppe von 1 bis 16 C-Atomen und R′ für H oder R. 3,4-(Methylendioxy)-brombenzole, in denen R′ = R ist, können aus dem käuflichen 3,4-(Methylendioxy)brombenzol durch Acetalspaltung und Umsetzung mit einer Verbindung R-CHO hergestellt werden (vgl. Beispiel 387). Aus (Ia1) läßt sich dann hydrierend (Ia2) erhalten.Scheme 1 shows the preparation of 1-alkyloxy-6-ethynylpyridine for example in the German patent application P 44 01 004.4 with the title "Phenanthrene derivatives and their use in liquid-crystalline mixtures"  is described, for example, the synthesis of the preferred compounds (Ia1). Therein R represents an optionally substituted by -O- or -Si (CH₃) ₂- Alkyl group of 1 to 16 carbon atoms and R ′ for H or R. 3,4- (methylenedioxy) bromobenzenes in which R ′ = R can be obtained from the commercially available 3,4- (methylenedioxy) bromobenzene by acetal splitting and reaction be prepared with a compound R-CHO (cf. Example 387). From (Ia1) can then be obtained by hydrogenation (Ia2).

Schema 2 zeigt die Synthese der bevorzugten Verbindung (Ia4) und (Ia5). Für die photochemische Cyclisierung kann das cis-trans-Gemisch der aus der Wittig- Reaktion anfallenden Ethen-Derivate eingesetzt werden. Bezüglich der Verfügbarkeit von 3,4-(Methylendioxy)-benzaldehyden, in denen R′ ≠ H ist, sei auf die Ausführungen zu Schema 1 verwiesen.Scheme 2 shows the synthesis of the preferred compounds (Ia4) and (Ia5). For the photochemical cyclization can be the cis-trans mixture from the Wittig Reaction resulting ethene derivatives are used. Regarding the Availability of 3,4- (methylenedioxy) benzaldehydes in which R ′ ≠ H is refer to the explanations for Scheme 1.

Schema 3 zeigt, im wesentlichen analog zu Schema 2, die Synthese der bevorzugten Verbindungen (Ia7) und (Ia8).Scheme 3 shows, essentially analogous to Scheme 2, the synthesis of the preferred compounds (Ia7) and (Ia8).

Schema 4 zeigt die Synthese der bevorzugten Verbindungen (Ia10) und (Ia11), wobei für die Ausführungen zur Wittig-Reaktion auf Schema 2 verwiesen wird. Die entsprechenden Triphenylphosphoniumsalze mit 3,4-(Methylendioxy)phenyl- Fragment sind aus den entsprechenden, teilweise käuflichen Aldehyden durch Reduktion mit LiAlH₄ zu den Benzylalkoholen, Überführung dieser in die Benzylbromide, mit z. B. Triphenylphosphin/Brom in CCl₄, und schließlich Umsetzung mit Triphenylphosphin in Toluol erhältlich.Scheme 4 shows the synthesis of the preferred compounds (Ia10) and (Ia11), reference is made to scheme 2 for the explanations of the Wittig reaction. The corresponding triphenylphosphonium salts with 3,4- (methylenedioxy) phenyl Fragments are made from the corresponding, partially commercially available aldehydes Reduction with LiAlH₄ to the benzyl alcohols, conversion into the Benzyl bromides, with e.g. B. triphenylphosphine / bromine in CCl₄, and finally Reaction with triphenylphosphine available in toluene.

Schema 5 zeigt die Herstellung der bevorzugten Verbindungen (Ia3) durch sauer­ katalysierte Azomethin-Bildung aus einem 6-substituierten Pyridin-2- carbaldehyd, der analog J. Heterocyclic Chem. 1966, 3, 357 hergestellt werden kann, und käuflichen, oder wie in Schema 2 erläutert, leicht aus käuflichen Edukten zugänglichen Anilin-Derivaten. Scheme 5 shows the preparation of the preferred compounds (Ia3) by acid catalyzed azomethine formation from a 6-substituted pyridine-2- carbaldehyde, which are prepared analogously to J. Heterocyclic Chem. 1966, 3, 357 can, and commercially, or as explained in Scheme 2, easily from commercial Aniline derivatives accessible to educts.  

Schemata 6 und 7 zeigen, analog zu Schema 5, die Synthese der bevorzugten Verbindungen (Ia6) und (Ia9), wobei eine analoge Vorgehensweise auch für die Verbindungen (Ia12) geeignet ist.Schemes 6 and 7, analogous to Scheme 5, show the synthesis of the preferred ones Compounds (Ia6) and (Ia9), an analogous procedure also for the Compounds (Ia12) is suitable.

Schema 8 zeigt den Syntheseweg für die bevorzugten Verbindungen (Ib7) und (Ib8); die generelle Vorgehensweise ist analog den vorherigen Schemata.Scheme 8 shows the synthetic route for the preferred compounds (Ib7) and (Ib8); the general procedure is analogous to the previous schemes.

Schema 9 zeigt, wie nach den bereits angeführten Verfahren Verbindungen erhalten werden, die zu den bevorzugten Strukturen (Ib1) und (Ib2) gehören.Scheme 9 shows how compounds are made according to the methods already mentioned are obtained which belong to the preferred structures (Ib1) and (Ib2).

Die bereits mehrfach angeführte Wittig-Reaktion ermöglicht, wie in Schema 10 aufgeführt, den Zugang zu den bevorzugten Verbindungen (Ib10) bzw. (Ib11).The Wittig reaction, which has already been mentioned several times, enables, as in Scheme 10 listed, access to the preferred compounds (Ib10) or (Ib11).

Auch für die Schemata 11 bis 14 sind die Schlüsselreaktionen, Azomethin- Bildung und photochemische Cyclisierung, bereits oben beschrieben. For Schemes 11 to 14, too, the key reactions, azomethine Formation and photochemical cyclization, already described above.  

Schema 1 Scheme 1

Schema 2 Scheme 2

Schema 3 Scheme 3

Schema 4 Scheme 4

Schema 5 Scheme 5

Schema 6 Scheme 6

Schema 7 Scheme 7

Schema 8 Scheme 8

Schema 9 Scheme 9

Schema 10 Scheme 10

Schema 11 Scheme 11

Schema 12 Scheme 12

Schema 13 Scheme 13

Schema 14 Scheme 14

Die Synthese der Reste R¹-(A¹)-(-M¹) und R² oder geeigneter reaktiver Derivate davon oder auch anderer geeigneter Vorläufer dieser Gruppierungen erfolgt nach an sich bekannten, dem Fachmann geläufigen Methoden.The synthesis of the residues R¹- (A¹) - (- M¹) and R² or suitable reactive derivatives of these or other suitable precursors of these groups follows known methods known to those skilled in the art.

Die Herstellung erfolgt dabei unter Reaktionsbedingungen, die für die genannten Umsetzungen bekannt und geeignet sind. Dabei kann auch von an sich bekannten, hier nicht näher erwähnten Varianten Gebrauch machen.The production takes place under reaction conditions for the above Implementations are known and suitable. It can also by itself make use of known variants not mentioned here.

Beispielsweise sei verwiesen auf DE-A 23 44 732, 24 50 088, 24 29 093, 25 02 94, 26 36 684, 27 01 591 und 27 52 975 für Verbindungen mit 1,4- Cyclohexylen und 1,4-Phenylen-Gruppen; DE-A 26 41 724 für Verbindungen mit Pyrimidin-2,5-diyl-Gruppen; DE-A 40 26 223 und EP-A 03 91 203 für Verbindungen mit Pyridin-2,5-diyl-Gruppen; EP-A 309 514 für Verbindungen mit (1,3,4)-Thiadiazol-2-5-diyl-Gruppen;
Die Herstellung disubstituierter Pyridine und disubstituierter Pyrimidine findet sich beispielsweise auch in den entsprechenden Bänden der Serie "The Chemistry of Heterocyclic Compounds" von A. Weissberger und E. C. Taylor (Herausgeber).For example, reference is made to DE-A 23 44 732, 24 50 088, 24 29 093, 25 02 94, 26 36 684, 27 01 591 and 27 52 975 for compounds with 1,4-cyclohexylene and 1,4-phenylene groups ; DE-A 26 41 724 for compounds with pyrimidine-2,5-diyl groups; DE-A 40 26 223 and EP-A 03 91 203 for compounds with pyridine-2,5-diyl groups; EP-A 309 514 for compounds with (1,3,4) thiadiazole-2-5-diyl groups;
The production of disubstituted pyridines and disubstituted pyrimidines can also be found, for example, in the corresponding volumes of the series "The Chemistry of Heterocyclic Compounds" by A. Weissberger and EC Taylor (editor).

Dioxanderivate werden zweckmäßig durch Reaktion eines entsprechenden Aldehyds (oder eines seiner reaktionsfähigen Derivate) mit einem entsprechenden 1,3-Diol (oder einem seiner reaktionsfähigen Derivate) hergestellt, vorzugsweise in Gegenwart eines inerten Lösungsmittels, wie Benzol oder Toluol, und/oder eines Katalysators, z. B. einer starken Säure, wie Schwefelsäure, Benzol- oder p-Toluolsulfonsäure, bei Temperaturen zwischen etwa 20°C und etwa 150°C, vorzugsweise zwischen 80°C und 120°C. Als reaktionsfähige Derivate der Ausgangsstoffe eignen sich in erster Linie Acetale.Dioxane derivatives are useful by reacting an appropriate one Aldehyde (or one of its reactive derivatives) with a corresponding 1,3-diol (or one of its reactive derivatives) prepared, preferably in the presence of an inert solvent such as benzene or toluene, and / or a catalyst, e.g. B. a strong acid, such as Sulfuric acid, benzene or p-toluenesulfonic acid, at temperatures between about 20 ° C and about 150 ° C, preferably between 80 ° C and 120 ° C. As reactive derivatives of the starting materials are primarily suitable for acetals.

Die genannten Aldehyde und 1,3-Diole sowie ihre reaktionsfähigen Derivate sind zum Teil bekannt, zum Teil können sie ohne Schwierigkeiten nach Standardverfahren der Organischen Chemie aus literaturbekannten Verbindungen hergestellt werden. Beispielsweise sind die Aldehyde durch Oxydation entsprechender Alkohole oder durch Reduktion von Nitrilen oder entsprechenden Carbonsäuren oder ihrer Derivate, die Diole durch Reduktion entsprechender Diester erhältlich.The aldehydes and 1,3-diols mentioned and their reactive derivatives are partly known, partly they can be followed without difficulty Standard methods of organic chemistry from literature  Connections are made. For example, the aldehydes are through Oxidation of appropriate alcohols or by reduction of nitriles or corresponding carboxylic acids or their derivatives, the diols by reduction corresponding diester available.

Verbindungen, worin ein aromatischer Ring durch mindestens ein F-Atom substituiert ist, können auch aus den entsprechenden Diazoniumsalzen durch Austausch der Diazoniumgruppe gegen ein Fluoratom, z. B. nach den Methoden von Balz und Schiemann, erhalten werden.Compounds in which an aromatic ring has at least one F atom is substituted, can also from the corresponding diazonium salts Exchange of the diazonium group for a fluorine atom, e.g. B. according to the methods from Balz and Schiemann.

Ester der Formel (I) können auch durch Veresterung entsprechender Carbonsäuren (oder ihrer reaktionsfähigen Derivate) mit Alkoholen bzw. Phenolen (oder ihren reaktionsfähigen Derivaten) oder nach der DCCI-Methode (DCCI = Dicyclohexylcarbodiimid) erhalten werden.Esters of the formula (I) can also be correspondingly esterified Carboxylic acids (or their reactive derivatives) with alcohols or Phenols (or their reactive derivatives) or by the DCCI method (DCCI = dicyclohexylcarbodiimide) can be obtained.

Die entsprechenden Carbonsäuren und Alkohole bzw. Phenole sind bekannt und können in Analogie zu bekannten Verfahren hergestellt werden.The corresponding carboxylic acids and alcohols or phenols are known and can be produced in analogy to known processes.

Als reaktionsfähige Derivate der genannten Carbonsäuren eignen sich insbesondere die Säurehalogenide, vor allem die Chloride und Bromide, ferner die Anhydride, z. B. auch gemischte Anhydride, Azide oder Ester, insbesondere Alkylester mit 1-4 C-Atomen in der Alkylgruppe.Suitable reactive derivatives of the carboxylic acids mentioned are especially the acid halides, especially the chlorides and bromides the anhydrides, e.g. B. also mixed anhydrides, azides or esters, in particular Alkyl esters with 1-4 C atoms in the alkyl group.

Als reaktionsfähige Derivate der genannten Alkohole bzw. Phenole kommen insbesondere die entsprechenden Metallalkoholate bzw. Phenolate, vorzugsweise eines Alkalimetalls, wie Natrium oder Kalium, in Betracht.Coming as reactive derivatives of the alcohols or phenols mentioned in particular the corresponding metal alcoholates or phenolates, preferably an alkali metal such as sodium or potassium.

Die Veresterung wird vorteilhaft in Gegenwart eines inerten Lösungsmittels durchgeführt. Gut geeignet sind insbesondere Ether, wie Diethylether, Di-n- butylether, THF, Dioxan oder Anisol, Ketone, wie Aceton, Butanon oder Cyclohexanon, Amide, wie DMF oder Phosphorsäurehexamethyltriamid, Kohlenwasserstoffe, wie Benzol, Toluol oder Xylol, Halogenkohlenwasserstoffe, wie Tetrachlorkohlenstoff, Dichlormethan oder Tetrachlorethylen und Sulfoxide, wie Dimethylsulfoxid oder Sulfolan.The esterification is advantageous in the presence of an inert solvent carried out. Particularly suitable are ethers, such as diethyl ether, di-n- butyl ether, THF, dioxane or anisole, ketones such as acetone, butanone or Cyclohexanone, amides, such as DMF or phosphoric acid hexamethyltriamide, Hydrocarbons, such as benzene, toluene or xylene, halogenated hydrocarbons,  such as carbon tetrachloride, dichloromethane or tetrachlorethylene and sulfoxides, such as dimethyl sulfoxide or sulfolane.

Ether der Formel (I) sind durch Veretherung entsprechender Hydroxyverbindungen, vorzugsweise entsprechender Phenole, erhältlich, wobei die Hydroxyverbindung zweckmäßig zunächst in ein entsprechendes Metallderivat, z. B. durch Behandeln mit NaH, NaNH₂, NaOH, KOH, Na₂CO₃ oder K₂CO₃ in das entsprechende Alkalimetallalkoholat oder Alkalimetallphenolat übergeführt wird. Dieses kann dann mit dem entsprechenden Alkylhalogenid, Sulfonat oder Dialkylsulfat umgesetzt werden, zweckmäßig in einem inerten Lösungsmittel, wie Aceton, 1,2-Dimethoxyethan, DMF oder Dimethylsulfoxid, oder auch mit einem Überschuß an wäßriger oder wäßrig-alkoholischer NaOH oder KOH bei Temperaturen zwischen etwa 200 und 100°C.Ethers of the formula (I) are more appropriate by etherification Hydroxy compounds, preferably corresponding phenols, are available, where the hydroxy compound expediently first in a corresponding Metal derivative, e.g. B. by treatment with NaH, NaNH₂, NaOH, KOH, Na₂CO₃ or K₂CO₃ in the corresponding alkali metal alcoholate or alkali metal phenolate is transferred. This can then be combined with the corresponding alkyl halide, Sulfonate or dialkyl sulfate are implemented, advantageously in an inert Solvents such as acetone, 1,2-dimethoxyethane, DMF or dimethyl sulfoxide, or with an excess of aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 200 and 100 ° C.

Was die Synthese spezieller Reste R¹ und R² angeht, sei zusätzlich beispielsweise verwiesen auf EP-A 0 355 008 für Verbindungen mit siliziumhaltigen Seitenketten und EP-A 0 292 954 und EP-A 0 398 155 für Verbindungen mit Cyclopropylgruppen in der Seitenkette.Regarding the synthesis of special R¹ and R² residues, is additional for example, refer to EP-A 0 355 008 for compounds with silicon-containing side chains and EP-A 0 292 954 and EP-A 0 398 155 for Compounds with cyclopropyl groups in the side chain.

Mit der Bereitstellung von Verbindungen der Formel (I) wird ganz allgemein die Palette der flüssigkristallinen Substanzen, die sich unter verschiedenen anwendungstechnischen Gesichtspunkten zur Herstellung flüssigkristalliner Gemische eignen, erheblich verbreitert.With the provision of compounds of formula (I), the Range of liquid crystalline substances, which are among different technical aspects for the production of liquid crystalline Mixtures are suitable, considerably widened.

In diesem Zusammenhang besitzen die Verbindungen der Formel I einen breiten Anwendungsbereich. In Abhängigkeit von der Auswahl der Substituenten können diese Verbindungen als Basismaterialien dienen, aus denen flüssigkristalline smektische, insbesondere ferroelektrische Phasen zum überwiegenden Teil zusammengesetzt sind; es können aber auch Verbindungen der Formel (I) flüssigkristallinen Basismaterialien aus anderen Verbindungsklassen zugesetzt werden, um beispielsweise die dielektrische und/oder optische Anisotropie und/oder die Viskosität und/oder die spontane Polarisation und/oder den Phasenbereiche und/oder den Tiltwinkel und/oder den Pitch eines solchen Dielektrikums zu variieren.In this connection, the compounds of formula I have a wide range Scope of application. Depending on the choice of substituents these compounds can serve as base materials from which liquid-crystalline smectic, especially ferroelectric phases for the majority are composed; but connections can also be made of the formula (I) liquid-crystalline base materials from others Classes of compound are added, for example the dielectric and / or optical anisotropy and / or the viscosity and / or the spontaneous  Polarization and / or the phase ranges and / or the tilt angle and / or the To vary the pitch of such a dielectric.

Besonders geeignet sind die Verbindungen der Formel (I), um schon in geringen Zumischungen die dielektrische Anisotropie, z. B. einer Flüssigkristallmischung in Richtung auf höhere negative Werte von Δ ε, zu beeinflussen.The compounds of formula (I) are particularly suitable, even in small amounts Admixtures the dielectric anisotropy, e.g. B. a liquid crystal mixture in Direction towards higher negative values of Δ ε.

Gegenstand der Erfindung ist auch die Verwendung von Verbindungen der Formel (I) in Flüssigkristallmischungen, vorzugsweise ferroelektrischen, antiferroelektrischen und nematischen, insbesondere ferroelektrischen.The invention also relates to the use of compounds of Formula (I) in liquid crystal mixtures, preferably ferroelectric, antiferroelectric and nematic, especially ferroelectric.

Weiterhin Gegenstand der Erfindung sind Flüssigkristallmischungen, vorzugsweise ferroelektrische, antiferroelektrische und nematische, insbesondere ferroelektrische, enthaltend eine oder mehrere Verbindungen der Formel (I), vorzugsweise der Formel (Ia).The invention furthermore relates to liquid crystal mixtures, preferably ferroelectric, antiferroelectric and nematic, in particular ferroelectric, containing one or more compounds of the Formula (I), preferably of formula (Ia).

Die erfindungsgemäßen Flüssigkristallmischungen enthalten im allgemeinen 2 bis 35, vorzugsweise 2 bis 25, besonders bevorzugt 2 bis 20 Komponenten.The liquid crystal mixtures according to the invention generally contain 2 to 35, preferably 2 to 25, particularly preferably 2 to 20 components.

Sie enthalten im allgemeinen 0,01 bis 80 Gew.-%, vorzugsweise 0,1 bis 60 Gew.-%, besonders bevorzugt 0,1 bis 30 Gew.-%, an einer oder mehreren, vorzugsweise 1 bis 10, besonders bevorzugt 1 bis 5, ganz besonders bevorzugt 1 bis 3, der erfindungsgemäßen Verbindungen der Formel (I).They generally contain 0.01 to 80 wt .-%, preferably 0.1 to 60 % By weight, particularly preferably 0.1 to 30% by weight, of one or more, preferably 1 to 10, particularly preferably 1 to 5, very particularly preferably 1 to 3, the compounds of formula (I) according to the invention.

Weitere Komponenten von Flüssigkristallmischungen, die erfindungsgemäße Verbindungen der Formel (I) enthalten, werden vorzugsweise ausgewählt aus den bekannten Verbindungen mit smektischen und/oder nematischen und/oder cholesterischen Phasen.Other components of liquid crystal mixtures, the invention Compounds of formula (I) are preferably selected from the known compounds with smectic and / or nematic and / or cholesteric phases.

  • - Derivate des Phenylpyrimidins, wie beispielsweise in WO 86/06401, US-A 4 874 542 beschrieben,Derivatives of phenylpyrimidine, as for example in WO 86/06401, US-A 4 874 542,
  • - metasubstituierte Sechsringaromaten, wie beispielsweise in der EP-A 0 578 054 beschrieben,- Meta-substituted six-ring aromatics, such as in the  EP-A 0 578 054,
  • - Siliziumverbindungen, wie beispielsweise in EP-A 0 355 008 beschrieben,Silicon compounds, as described for example in EP-A 0 355 008,
  • - mesogene Verbindungen mit nur einer Seitenkette, wie in EP-A 0 541 081 beschrieben,- mesogenic connections with only one side chain, as in EP-A 0 541 081,
  • - Hydrochinonderivate, wie beispielsweise in EP-A 0 603 786 beschrieben,- Hydroquinone derivatives, such as in EP-A 0 603 786,
  • - Pyridylpyrimidine, wie beispielsweise in WO 92/12974 beschrieben,Pyridylpyrimidines, as described for example in WO 92/12974,
  • - Phenylbenzoate, wie beispielsweise bei P. Keller, Ferroelectrics 58 (1984), 3 und J. W. Goodby et al, Liquid Crystals and Ordered Fluids, Bd. 4, New York 1984 beschrieben und- Phenylbenzoates, such as from P. Keller, Ferroelectrics 58 (1984), 3 and J.W. Goodby et al, Liquid Crystals and Ordered Fluids, 4, New York 1984 and
  • - Thiadiazole, wie beispielsweise in EP-B 309 514 beschrieben.Thiadiazoles, as described for example in EP-B 309 514.

Als chirale, nicht racemische Dotierstoffe kommen beispielsweise in Frage:Examples of chiral, non-racemic dopants are:

  • - optisch aktive Phenylbenzoate, wie beispielsweise bei P. Keller, Ferroelectrics 58 (1984), 3 und J. W. Goodby et al, Liquid Crystals and Ordered Fluids, Bd. 4, New York 1984 beschrieben,optically active phenylbenzoates, such as, for example, P. Keller, Ferroelectrics 58 (1984), 3 and J.W. Goodby et al, Liquid Crystals and Ordered Fluids, Vol. 4, New York 1984,
  • - optisch aktive Oxiranether, wie beispielsweise in EP-A 0 263 437 und WO-A 93/13093 beschrieben,- Optically active oxirane ethers, such as in EP-A 0 263 437 and WO-A 93/13093,
  • - optisch aktive Oxiranester, wie beispielsweise in EP-A 0 292 954 beschrieben,- Optically active oxirane esters, as for example in EP-A 0 292 954 described
  • - optisch aktive Dioxolanether, wie beispielsweise in EP-A 0 351 746 beschrieben,optically active dioxolane ethers, such as, for example, in EP-A 0 351 746 described
  • - optisch aktive Dioxolanester, wie beispielsweise in EP-A 0 361 272 beschrieben, und- Optically active dioxolane esters, such as, for example, in EP-A 0 361 272 described, and
  • - optisch aktive Tetrahydrofuran-2-carbonsäureester, wie beispielsweise in EP-A 0 355 561 beschrieben.- Optically active tetrahydrofuran-2-carboxylic acid esters, such as in EP-A 0 355 561.

Die Mischungen wiederum können Anwendung finden in elektrooptischen oder vollständig optischen Elementen, z. B. Anzeigeelementen, Schaltelementen, Lichtmodulatoren, Elementen zur Bildbearbeitung und/oder Signalverarbeitung oder allgemein im Bereich der nichtlinearen Optik. The mixtures in turn can be used in electro-optical or completely optical elements, e.g. B. display elements, switching elements, Light modulators, elements for image processing and / or signal processing or generally in the field of nonlinear optics.  

Flüssigkristalline Mischungen, die Verbindungen der allgemeinen Formel (I) enthalten, sind besonders für die Verwendung in elektrooptischen Schalt- und Anzeigevorrichtungen (Displays) geeignet. Diese Displays sind üblicherweise so aufgebaut, daß eine Flüssigkristallschicht beiderseitig von Schichten eingeschlossen ist, die üblicherweise, in dieser Reihenfolge ausgehend von der LC-Schicht, mindestens eine Orientierungsschicht, Elektroden und eine Begrenzungsscheibe (z. B. aus Glas) sind. Darüberhinaus enthalten sie Abstandshalter, Kleberahmen, Polarisatoren sowie für Farbdisplays dünne Farbfilterschichten. Weitere mögliche Komponenten sind Antireflex-, Passivierungs-, Ausgleichs- und Sperrschichten sowie elektrisch-nichtlineare Elemente, wie Dünnschichttransistoren (TFT) und Metall-Isolator-Metall-(MIM)- Elemente. Im Detail ist der Aufbau von Flüssigkristalldisplays bereits in einschlägigen Monographien beschrieben (siehe z. B. E. Kaneko, "Liquid Crystal TV Displays: Principles and Applications of Liquid Crystal Displays", KTK Scientific Publishers 1987).Liquid-crystalline mixtures, the compounds of the general formula (I) included, are especially for use in electro-optical switching and Suitable display devices. These displays are usually like this built that a liquid crystal layer on both sides of layers is included, which is usually in that order starting from the LC layer, at least one orientation layer, electrodes and one Boundary disk (e.g. made of glass). They also contain Spacers, adhesive frames, polarizers and thin ones for color displays Color filter layers. Other possible components are anti-reflective, Passivation, compensation and barrier layers as well as non-linear electrical Elements such as thin film transistors (TFT) and metal insulator metal (MIM) - Elements. The structure of liquid crystal displays is already in detail relevant monographs (see, for example, E. Kaneko, "Liquid Crystal TV Displays: Principles and Applications of Liquid Crystal Displays ", KTK Scientific Publishers 1987).

Ferner sind die Mischungen für Feldbehandlung, d. h. zum Betrieb in der Quasi- Bookshelf-Geometrie (QBG), (siehe z. B. H. Rieger et al, SID 91 Digest (Anaheim) 1991, 396), geeignet.Furthermore, the mixtures for field treatment, i.e. H. for operation in the quasi Bookshelf geometry (QBG), (see e.g. H. Rieger et al, SID 91 Digest (Anaheim) 1991, 396).

Ebenso sind die erfindungsgemäßen Mischungen geeignet für die Verwendung in ferroelektrischen Flüssigkristallanzeigen, die auf Nutzung des DHF-Effekts oder des PSFLCD-Effekts (Pitch Stabilized Ferroelectric Liquid Crystal Display, auch SBF = Short Pitch Bistable Ferroelectric Effect genannt) beruhen.The mixtures according to the invention are also suitable for use in ferroelectric liquid crystal displays based on the use of the DHF effect or the PSFLCD effect (Pitch Stabilized Ferroelectric Liquid Crystal Display, too SBF = Short Pitch Bistable Ferroelectric Effect).

Die Erfindung wird durch die nachfolgenden Beispiele weiter erläutert, ohne sie dadurch beschränken zu wollen.The invention is further illustrated by the following examples without it wanting to restrict it.

Beispiel 1example 1 9-Decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Eine Mischung aus 2.0 g 1-(6-Hexyloxy-pyridin-2-yl)ethin (hergestellt wie in DE-A 44 01 004 beschrieben), 3.3 g 5-Brom-2-decyl-indan (hergestellt wie in EP-A 546 338 beschrieben), 0.13 g Bis(triphenylphosphin)palladium(II)chlorid, 0.02 g Kupfer(I)iodid, 5.4 g Kalciumcarbonat und 50 ml DMF wird 90 min bei 100°C gerührt. Nach Zugabe von 100 ml Wasser wird dreimal mit je 100 ml Dichlormethan extrahiert, die vereinigten organischen Phasen mit Na₂SO₄ getrocknet, im Vakuum zur Trockene gebracht und an Kieselgel mit Dichlormethan/Heptan 4 : 6 chromatographiert. Man erhält 2.0 g 1-(2-Decyl- indan-5-yl)-2-(6-hexyloxy-pyridin-2-yl)ethin als schwach gelbliches zähes Öl.A mixture of 2.0 g of 1- (6-hexyloxypyridin-2-yl) ethyne (prepared as in  DE-A 44 01 004), 3.3 g of 5-bromo-2-decyl-indan (prepared as in EP-A 546 338), 0.13 g bis (triphenylphosphine) palladium (II) chloride, 0.02 g of copper (I) iodide, 5.4 g of calcium carbonate and 50 ml of DMF are added for 90 min 100 ° C stirred. After adding 100 ml of water three times with 100 ml each Extracted dichloromethane, the combined organic phases with Na₂SO₄ dried, brought to dryness in vacuo and on silica gel Chromatographed dichloromethane / heptane 4: 6. 2.0 g of 1- (2-decyl- indan-5-yl) -2- (6-hexyloxypyridin-2-yl) ethyne as a pale yellowish viscous oil.

Eine Lösung von 2.0 g 1-(2-Decyl-indan-5-yl)-2-(6-hexyloxy-pyridin-2-yl)ethin in 50 ml Pyridin wird mit 0.2 g Pd/BaSO₄ (10%) versetzt. Man hydriert bei Raumtemperatur bis zu einer Wasserstoffaufnahme von 120 ml. Danach werden 300 ml 10 gew.-%ige wäßrige Chlorwasserstoffsäure zugegeben und dreimal mit je 100 ml Dichlormethan extrahiert. Nach Trocknen und Eindampfen der vereinigten organischen Phasen werden 1.9 g (Z)-1-(2-Decyl-indan-5-yl)-2(6- hexyloxy-pyridin-2-yl)ethen als leicht gelbliches zähes Öl erhalten.A solution of 2.0 g of 1- (2-decyl-indan-5-yl) -2- (6-hexyloxypyridin-2-yl) ethyne in 50 ml of pyridine is mixed with 0.2 g of Pd / BaSO₄ (10%). One hydrogenates Room temperature up to a hydrogen intake of 120 ml. Then 300 ml of 10% by weight aqueous hydrochloric acid were added and three times extracted with 100 ml dichloromethane. After drying and evaporating the combined organic phases are 1.9 g (Z) -1- (2-decyl-indan-5-yl) -2 (6- Obtained hexyloxy-pyridin-2-yl) ethene as a slightly yellowish viscous oil.

Eine Lösung von 1 g (Z)-1-(2-Decyl-indan-5-yl)-2-(6-hexyloxy-pyridin-2-yl)ethen in 750 ml Cyclohexan wird unter Zusatz von 0.1 g Iod 16 h in einer Quarzapparatur mit dem Licht einer UV-Lampe (TQ 150, Fa. Heraeus) bestrahlt. Nach Zugabe gesättigter, wäßriger Natriumsulfitlösung wird die organische Phase zweimal mit Wasser gewaschen, mit Natriumsulfat getrocknet und im Vakuum eingedampft. Nach Chromatographie an Kieselgel mit Dichlormethan/Heptan 1 : 1 und Umkristallisation aus Ethanol werden 0.3 g 9-Decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren als farblose Kristalle mit der Phasenfolge X 71 S₁ 80 l erhalten.A solution of 1 g of (Z) -1- (2-decyl-indan-5-yl) -2- (6-hexyloxypyridin-2-yl) ethene in 750 ml of cyclohexane with the addition of 0.1 g of iodine for 16 h in a Quartz apparatus irradiated with the light of a UV lamp (TQ 150, Heraeus). After adding saturated, aqueous sodium sulfite solution, the organic Phase washed twice with water, dried with sodium sulfate and in Evaporated vacuum. After chromatography on silica gel with Dichloromethane / heptane 1: 1 and recrystallization from ethanol become 0.3 g 9-decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene as colorless crystals with the phase sequence X 71 S₁ 80 l obtained.

Analog werden erhalten:The following are obtained analogously:

Beispiel 1example 1

9-Decyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 3Example 3

9-Decyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 4Example 4

9-Decyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren 9-decyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene  

Beispiel 5Example 5

9-Decyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 6Example 6

9-Decyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 7Example 7

9-Decyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 8Example 8

9-Decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 9Example 9

9-Decyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 10Example 10

9-Decyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 11Example 11

9-Decyl-3-(6-methyl)octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phen-anthren9-decyl-3- (6-methyl) octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phen-anthrene

Beispiel 12Example 12

9-Decyl-3-(1-methyl)heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b] phenanthren9-decyl-3- (1-methyl) heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 13Example 13

9-Decyl-3-(5-cyclopropyl)pentyloxy-9,10-dihydro-8H-4-aza- cyclopenta[b]-phenanthren9-decyl-3- (5-cyclopropyl) pentyloxy-9,10-dihydro-8H-4-aza- cyclopenta [b] phenanthrene

Beispiel 14Example 14

9-Decyl-3-[4-(butyl-dimethylsilyl)]butyloxy-9,10-dihydro-8H-4-aza- cyclopenta[b]-phenanthren9-decyl-3- [4- (butyl-dimethylsilyl)] butyloxy-9,10-dihydro-8H-4-aza- cyclopenta [b] phenanthrene

Beispiel 15Example 15

9-Decyl-3-[(R)-2-fluor]octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b] phenanthren9-decyl-3 - [(R) -2-fluoro] octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 16Example 16

9-Decyl-3-(1H,1H-perfluor-octyloxy)-9,10-dihydro-8H-4-aza- cyclopenta[b]-phenanthren9-decyl-3- (1H, 1H-perfluoro-octyloxy) -9,10-dihydro-8H-4-aza- cyclopenta [b] phenanthrene

Beispiel 17Example 17

9-Decyl-3-(5-oxa-nonyloxy)-9,10-dihydro-8H-4-aza-cyclopenta[b]phenan-thren9-decyl-3- (5-oxa-nonyloxy) -9,10-dihydro-8H-4-aza-cyclopenta [b] phenane-thren

Beispiel 18Example 18

9-Decyl-3-(9-decen-1-yl)oxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phena-nthren9-decyl-3- (9-decen-1-yl) oxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phena-nhrene

Beispiel 19Example 19

9-Decyl-3-nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]-phenanthren9-decyl-3-nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] -phenanthrene

Beispiel 20Example 20

9-Decyl-3-(7-methyl)nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phen-anthren9-decyl-3- (7-methyl) nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phen-anthrene

Beispiel 21Example 21

9-Decyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]-phenanthren9-decyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] -phenanthrene

Beispiel 22Example 22

9-Decyl-3-(8-methyl)decyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phen-anthren9-decyl-3- (8-methyl) decyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phen-anthrene

Beispiel 23Example 23

9-Decyl-3-undecyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-decyl-3-undecyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 24Example 24

9-Octyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-octyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 25Example 25

9-Octyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren 9-octyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene  

Beispiel 26Example 26

9-Octyl-3-difluormethoxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-octyl-3-difluoromethoxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 27Example 27

9-Octyl-3-trifluormethoxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-octyl-3-trifluoromethoxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 28Example 28

9-Octyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren9-octyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 29Example 29

9-Octyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren-9-octyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] -phenanthrene-

Beispiel 30Example 30

9-Decyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren9-decyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 31Example 31

9-Octyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren-9-octyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] -phenanthrene-

Beispiel 32Example 32

9-Octyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren9-octyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 33Example 33

9-Octyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren-9-octyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] -phenanthrene-

Beispiel 34Example 34

9-Octyl-3-(5-methyl)heptyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]­ phenanthren9-octyl-3- (5-methyl) heptyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] phenanthrene

Beispiel 35Example 35

9-Octyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]­ phenanthren9-octyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] phenanthrene

Beispiel 36Example 36

9-Octyl-3-(7-octen-1-yl)oxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]­ phenanthren9-octyl-3- (7-octen-1-yl) oxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] phenanthrene

Beispiel 37Example 37

9-Octyl-3-[(R)-1-ethoxycarbonyl]ethoxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]-phenanthren9-octyl-3 - [(R) -1-ethoxycarbonyl] ethoxy-9,10-dihydro-8H-4-aza-cyclo penta [b] -phenanthrene

Beispiel 38Example 38

9-Octyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]-phenanthren9-octyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 38Example 38

9-Hexyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-Hexyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 39Example 39

9-Hexyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 41Example 41

9-Hexyl-3-difluormethoxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-hexyl-3-difluoromethoxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 42Example 42

9-Hexyl-3-trifluormethoxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-hexyl-3-trifluoromethoxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 43Example 43

9-Hexyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclo-penta [b]phenanthren9-Hexyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 44Example 44

9-Hexyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]phenanthren9-Hexyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 45Example 45

9-Hexyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]phenanthren9-Hexyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 46Example 46

9-Hexyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]phenanthren9-Hexyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 47Example 47

9-Hexyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]phenanthren9-Hexyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 48Example 48

9-Hexyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo penta[b]phenanthren9-Hexyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 49Example 49

9-Hexyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b] phenanthren 9-Hexyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene  

Beispiel 50Example 50

9-Hexyl-3-[4-butyl-dimethylsilyl)-butyloxy]-9,10-dihydro-8H-4-aza-cy-clo­ penta[b]phenanthren9-Hexyl-3- [4-butyl-dimethylsilyl) butyloxy] -9,10-dihydro-8H-4-aza-cy-clo penta [b] phenanthrene

Beispiel 51Example 51

9-Pentyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-pentyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 52Example 52

9-Pentyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-pentyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 53Example 53

9-Pentyl-3-difluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b]phenanthren9-pentyl-3-difluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 54Example 54

9-Pentyl-3-trifluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b]phenanthren9-pentyl-3-trifluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 55Example 55

9-Pentyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren9-pentyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 56Example 56

9-Pentyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren-9-pentyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 57Example 57

9-Pentyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren9-pentyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 58Example 58

9-Pentyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren-9-pentyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene-

Beispiel 59Example 59

9-Pentyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren9-pentyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 60Example 60

9-Pentyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren-9-pentyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 61Example 61

9-Pentyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta-[b]phenanthren9-pentyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 62Example 62

9-Butyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-butyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 63Example 63

9-Butyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-butyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 64Example 64

9-Butyl-3-difluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanth-ren9-butyl-3-difluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthene

Beispiel 65Example 65

9-Butyl-3-trifluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenant-hren9-butyl-3-trifluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 66Example 66

9-Butyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta[b]-phenanthren9-butyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta [b] -phenanthrene

Beispiel 67Example 67

9-Butyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-butyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 68Example 68

9-Butyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-butyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 69Example 69

9-Butyl-3-difluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b]phenanthren9-butyl-3-difluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] phenanthrene

Beispiel 70Example 70

9-Butyl-3-trifluormethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenant-hren9-butyl-3-trifluoromethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 71Example 71

9-Butyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta[b]-phenanthren9-butyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta [b] -phenanthrene

Beispiel 72Example 72

9-Propyl-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-propyl-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 73Example 73

9-Propyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 74Example 74

9-Propyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren 9-propyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene  

Beispiel 75Example 75

9-Propyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 76Example 76

9-Propyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 77Example 77

9-Propyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 78Example 78

9-Propyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 79Example 79

9-Propyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 80Example 80

9-Propyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 81Example 81

9-Propyl-3-[(R)-2-fluor]hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b]penanthren9-propyl-3 - [(R) -2-fluoro] hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta- [b] penanthrene

Beispiel 82Example 82

9-Propyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta[b]penanthren9-propyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta [b] penanthrene

Beispiel 83Example 83

9-Ethyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 84Example 84

9-Ethyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 85Example 85

9-Ethyl-3-butoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-butoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 86Example 86

9-Ethyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 87Example 87

9-Ethyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 88Example 88

9-Ethyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 89Example 89

9-Ethyl-3-nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 90Example 90

9-Ethyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-decyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 91Example 91

9-Ethyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-ethyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 92Example 92

9-Methyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]-phenanthren9-methyl-3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] -phenanthrene

Beispiel 93Example 93

9-Methyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclo-penta[b]­ phenanthren9-methyl-3-pentyloxy-9,10-dihydro-8H-4-aza-cyclo-penta [b] phenanthrene

Beispiel 94Example 94

9-Methyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-methyl-3-hexyloxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 95Example 95

9-Methyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo­ penta[b]phenanthren9-methyl-3-heptyloxy-9,10-dihydro-8H-4-aza-cyclo penta [b] phenanthrene

Beispiel 96Example 96

9-Methyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-methyl-3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 97Example 97

9-Methyl-3-fluor-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren9-methyl-3-fluoro-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 98Example 98

3-Methoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-methoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 99Example 99

3-Ethoxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-ethoxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 100Example 100

3-Propyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-propyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 101Example 101

3-Butyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-butyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 102Example 102

3-Pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren 3-pentyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene  

Beispiel 103Example 103

3-Hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-hexyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 104Example 104

3-Heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-heptyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 105Example 105

3-Octyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren3-octyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene

Beispiel 106Example 106

3-Nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta[b]phenanthren.3-nonyloxy-9,10-dihydro-8H-4-aza-cyclopenta [b] phenanthrene.

Beispiel 107Example 107

9-Decyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren wird analog Beispiel 1, jedoch unter Verwendung von 3-Hexyloxy-brombenzol, erhalten.9-decyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene is analogous to Example 1, but using 3-hexyloxy-bromobenzene, receive.

Analog Beispiel 107 werden erhalten:Analogously to Example 107, the following are obtained:

Beispiel 108Example 108

9-Decyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 109Example 109

9-Decyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 110Example 110

9-Decyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 111Example 111

9-Decyl-3-decyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-decyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 112Example 112

9-Decyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 113Example 113

9-Decyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 114Example 114

9-Decyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 115Example 115

9-Decyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 116Example 116

9-Decyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 117Example 117

9-Decyl-9,10-dihydro-8H-cyclopenta[b]phenanthren9-decyl-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 118Example 118

9-Nonyl-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 119Example 119

9-Nonyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 120Example 120

9-Nonyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 121Example 121

9-Nonyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 122Example 122

9-Nonyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 123Example 123

9-Nonyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 124Example 124

9-Nonyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 125Example 125

9-Nonyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 126Example 126

9-Nonyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 127Example 127

9-Nonyl-3-(6-methyl)octyloxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-nonyl-3- (6-methyl) octyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 128Example 128

9-Nonyl-3-(1-methyl)heptyloxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3- (1-methyl) heptyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 129Example 129

9-Nonyl-3-(6-cyclopropyl)-hexyloxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3- (6-cyclopropyl) hexyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 130Example 130

9-Nonyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-nonyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 141Example 141

9-Nonyl-3-decyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-nonyl-3-decyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 142Example 142

9-Octyl-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 143Example 143

9-Octyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 144Example 144

9-Octyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 145Example 145

9-Octyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 146Example 146

9-Octyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 147Example 147

9-Octyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 148Example 148

9-Octyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 149Example 149

9-Octyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 150Example 150

9-Octyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 151Example 151

9-Octyl-3-[4-(butyl-dimethylsilyl)]butyloxy-9,10-dihydro-8H- cyclopenta[b]phenanthren9-octyl-3- [4- (butyl-dimethylsilyl)] butyloxy-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 152Example 152

9-Octyl-3-[(R)-2-fluor]octyloxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3 - [(R) -2-fluoro] octyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 153Example 153

9-Octyl-3-(1H,1H-perfluor-octyloxy)-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3- (1H, 1H-perfluoro-octyloxy) -9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 154Example 154

9-Octyl-3-(5-oxa-nonyloxy)-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3- (5-oxa-nonyloxy) -9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 155Example 155

9-Octyl-3-(9-decen-1-yl)oxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3- (9-decen-1-yl) oxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 156Example 156

9-Octyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-octyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 157Example 157

9-Octyl-3-decyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-octyl-3-decyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 158Example 158

9-Heptyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 159Example 159

9-Heptyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 160Example 160

9-Heptyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 161Example 161

9-Heptyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 162Example 162

9-Heptyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren 9-heptyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 163Example 163

9-Heptyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 164Example 164

9-Heptyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 165Example 165

9-Heptyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 166Example 166

9-Hexyl-3-[(R)-1-ethoxycarbonyl]ethoxy-9,10-dihydro-8H- cyclopenta[b]phenanthren9-hexyl-3 - [(R) -1-ethoxycarbonyl] ethoxy-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 167Example 167

9-Hexyl-3-[(2S,3S)-3-Butyl-oxiran-2-yl]methyloxy-9,10-dihydro-8H- cyclopenta[b]phenanthren9-hexyl-3 - [(2S, 3S) -3-butyl-oxiran-2-yl] methyloxy-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 168Example 168

9-Hexyl-3-[(2R,3R)-3-Butyl-oxiran-2-yl]carbonyloxy-9,10-dihydro-8H- cyclopenta[b]phenanthren9-hexyl-3 - [(2R, 3R) -3-butyl-oxiran-2-yl] carbonyloxy-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 169Example 169

9-Hexyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-hexyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 170Example 170

9-Hexyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 171Example 171

9-Hexyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 172Example 172

9-Hexyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-hexyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 173Example 173

9-Hexyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-hexyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 174Example 174

9-Hexyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-hexyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 175Example 175

9-Hexyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 176Example 176

9-Hexyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 177Example 177

9-Hexyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 178Example 178

9-Hexyl-3-decyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-hexyl-3-decyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 179Example 179

9-Hexyl-3-undecyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-undecyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 180Example 180

9-Hexyl-3-dodecyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-dodecyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 181Example 181

9-Hexyl-3-hexylcarbonyloxy-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-hexyl-3-hexylcarbonyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 182Example 182

9-Pentyl-3-methoxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-methoxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 183Example 183

9-Pentyl-3-ethoxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-ethoxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 184Example 184

9-Pentyl-3-propyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-propyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 185Example 185

9-Pentyl-3-butyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-butyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 186Example 186

9-Pentyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 187Example 187

9-Pentyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 188Example 188

9-Pentyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 189Example 189

9-Pentyl-3-octyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-pentyl-3-octyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 190Example 190

9-Pentyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren 9-pentyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 191Example 191

9-Butyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 192Example 192

9-Butyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 193Example 193

9-Butyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 194Example 194

9-Butyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 195Example 195

9-Butyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 196Example 196

9-Butyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 197Example 197

9-Butyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 198Example 198

9-Butyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 199Example 199

9-Butyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 200Example 200

9-Butyl-3-decyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-decyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 201Example 201

9-Propyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 202Example 202

9-Propyl-3-ethoxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren 9-propyl-3-ethoxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 203Example 203

9-Propyl-3-propyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-propyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 204Example 204

9-Propyl-3-butyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-butyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 205Example 205

9-Propyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 206Example 206

9-Propyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 207Example 207

9-Propyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 208Example 208

9-Propyl-3-octyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-octyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 209Example 209

9-Propyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 210Example 210

9-Propyl-3-decyloxy-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-propyl-3-decyloxy-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 211Example 211

9-Ethyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 212Example 212

9-Ethyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 213Example 213

9-Ethyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 214Example 214

9-Ethyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 215Example 215

9-Ethyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 216Example 216

9-Ethyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 217Example 217

9-Ethyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 218Example 218

9-Ethyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 219Example 219

9-Ethyl-3-nonyloxy9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-nonyloxy9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 220Example 220

9-Ethyl-3-decyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-decyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 221Example 221

9-Methyl-3-methoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-methoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 222Example 222

9-Methyl-3-ethoxy-9,10-dihydro-8H-cyclopenta[b]phenanthren 9-methyl-3-ethoxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 223Example 223

9-Methyl-3-propyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-propyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 224Example 224

9-Methyl-3-butyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-butyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 225Example 225

9-Methyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-pentyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 226Example 226

9-Methyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-hexyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 227Example 227

9-Methyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-heptyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 228Example 228

9-Methyl-3-octyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-octyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 229Example 229

9-Methyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-nonyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 230Example 230

9-Methyl-3-decyloxy-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-decyloxy-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 231Example 231

9-Decyl-3-hexyloxy-4-fluor-9,10-dihydro-cyclopenta[b]phenanthren wird analog Beispiel 107, jedoch unter Verwendung von 2-Brom-6-hexyloxy-fluorbenzol hergestellt.9-Decyl-3-hexyloxy-4-fluoro-9,10-dihydro-cyclopenta [b] phenanthrene becomes analogous Example 107, but using 2-bromo-6-hexyloxy-fluorobenzene manufactured.

Analog Beispiel 231 werden erhalten:Analogously to Example 231, the following are obtained:

Beispiel 232Example 232

9-Decyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 233Example 233

9-Decyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 234Example 234

9-Decyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 235Example 235

9-Decyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 236Example 236

9-Decyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 237Example 237

9-Decyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 238Example 238

9-Decyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-decyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 239Example 239

9-Decyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 240Example 240

9-Decyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-decyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 241Example 241

9-Decyl-4-fluor-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-decyl-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 242Example 242

9-Nonyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 243Example 243

9-Nonyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta-[b]phenanthren9-nonyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 244Example 244

9-Nonyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 245Example 245

9-Nonyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 246Example 246

9-Nonyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 247Example 247

9-Nonyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 248Example 248

9-Nonyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 249Example 249

9-Nonyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 250Example 250

9-Nonyl-3-(6-methyl)octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3- (6-methyl) octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 251Example 251

9-Nonyl-3-(1-methyl)heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3- (1-methyl) heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 252Example 252

9-Nonyl-3-(6-cyclopropyl)hexyloxy-4-fluor-9,10-dihydro-8H- cyclopenta-[b]phenanthren9-nonyl-3- (6-cyclopropyl) hexyloxy-4-fluoro-9,10-dihydro-8H- cyclopenta- [b] phenanthrene

Beispiel 253Example 253

9-Nonyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 254Example 254

9-Nonyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-nonyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 255Example 255

9-Octyl-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 256Example 256

9-Octyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren 9-octyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 257Example 257

9-Octyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 258Example 258

9-Octyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-octyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 259Example 259

9-Octyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 260Example 260

9-Octyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-octyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 261Example 261

9-Octyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 262Example 262

9-Octyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-octyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 263Example 263

9-Octyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 264Example 264

9-Octyl-3-[4-(butyl-dimethylsilyl)]butyloxy-4-fluor-9,10-dihydro-8H-- cyclopenta[b]phenanthren9-octyl-3- [4- (butyl-dimethylsilyl)] butyloxy-4-fluoro-9,10-dihydro-8H-- cyclopenta [b] phenanthrene

Beispiel 265Example 265

9-Octyl-3-[(R)-2-fluor]octyloxy-4-fluor-9,10-dihydro-8H- cyclopenta[b]phenanthren9-octyl-3 - [(R) -2-fluoro] octyloxy-4-fluoro-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 266Example 266

9-Octyl-3-(1H,1H-perfluor-octyloxy)-4-fluor-9,10-dihydro-8H- cyclopenta[b]phenanthren9-octyl-3- (1H, 1H-perfluoro-octyloxy) -4-fluoro-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 267Example 267

9-Octyl-3-(5-oxa-nonyloxy)-4-fluor-9,10-dihydro-8H-cyclopenta[b]phen-anthren9-octyl-3- (5-oxa-nonyloxy) -4-fluoro-9,10-dihydro-8H-cyclopenta [b] phen-anthrene

Beispiel 268Example 268

9-Octyl-3-(9-decen-1-yl)oxy-4-fluor-9,10-dihydro-8H-cyclopenta[b] phenanthren9-octyl-3- (9-decen-1-yl) oxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 269Example 269

9-Octyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 270Example 270

9-Octyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-octyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 271Example 271

9-Heptyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 272Example 272

9-Heptyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-heptyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 273Example 273

9-Heptyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 274Example 274

9-Heptyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 275Example 275

9-Heptyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 276Example 276

9-Heptyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 277Example 277

9-Heptyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 278Example 278

9-Heptyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-heptyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 279Example 279

9-Methyl-3-[(R)-1-ethoxycarbonyl]ethoxy-4-fluor-9,10-dihydro-8H- cyclopenta[b]phenanthren9-methyl-3 - [(R) -1-ethoxycarbonyl] ethoxy-4-fluoro-9,10-dihydro-8H- cyclopenta [b] phenanthrene

Beispiel 280Example 280

9-Methyl-3-[(2S,3S)-3-Butyl-oxiran-2-yl]methyloxy-4-fluor-9,10- dihydro-8H-cyclopenta[b]phenanthren9-methyl-3 - [(2S, 3S) -3-butyl-oxiran-2-yl] methyloxy-4-fluoro-9,10- dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 281Example 281

9-Methyl-3-[(2R,3R)-3-Butyl-oxiran-2-yl]carbonyloxy-4-fluor-9,10- dihydro-8H-cyclopenta[b]phenanthren9-methyl-3 - [(2R, 3R) -3-butyl-oxiran-2-yl] carbonyloxy-4-fluoro-9,10- dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 282Example 282

9-Methyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 283Example 283

9-Methyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 284Example 284

9-Methyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 285Example 285

9-Methyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 286Example 286

9-Methyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 287Example 287

9-Methyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 288Example 288

9-Methyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-methyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 289Example 289

9-Methyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 290Example 290

9-Methyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 291Example 291

9-Methyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 292Example 292

9-Methyl-3-undecyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-undecyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 293Example 293

9-Methyl-3-dodecyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-dodecyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 294Example 294

9-Methyl-3-hexylcarbonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-hexylcarbonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 295Example 295

9-Pentyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 296Example 296

9-Pentyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 297Example 297

9-Pentyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 298Example 298

9-Pentyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 299Example 299

9-Pentyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 300Example 300

9-Pentyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 301Example 301

9-Pentyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 302Example 302

9-Pentyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 303Example 303

9-Pentyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-pentyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 304Example 304

9-Butyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-butyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 305Example 305

9-Butyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 306Example 306

9-Butyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-butyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 307Example 307

9-Butyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 308Example 308

9-Butyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-butyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 309Example 309

9-Butyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 310Example 310

9-Butyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-butyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 311Example 311

9-Butyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 312Example 312

9-Butyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 313Example 313

9-Butyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 314Example 314

9-Propyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 315Example 315

9-Propyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 316Example 316

9-Propyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-propyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 317Example 317

9-Propyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-propyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 318Example 318

9-Propyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-propyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 319Example 319

9-Propyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-propyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 320Example 320

9-Propyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-propyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 321Example 321

9-Propyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren- 9-propyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 322Example 322

9-Propyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-propyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 323Example 323

9-Propyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-propyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 324Example 324

9-Ethyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 325Example 325

9-Ethyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 326Example 326

9-Ethyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-ethyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 327Example 327

9-Ethyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 328Example 328

9-Ethyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-ethyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 329Example 329

9-Ethyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 330Example 330

9-Ethyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-ethyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 331Example 331

9-Ethyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 332Example 332

9-Ethyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 333Example 333

9-Ethyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 334Example 334

9-Methyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 335Example 335

9-Methyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 336Example 336

9-Methyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren9-methyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene

Beispiel 337Example 337

9-Methyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta- [b]phenanthren 9-methyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta- [b] phenanthrene  

Beispiel 338Example 338

9-Methyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-methyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 339Example 339

9-Methyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 340Example 340

9-Methyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-methyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 341Example 341

9-Methyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 342Example 342

9-Methyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 343Example 343

9-Methyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 344Example 344

9-Methyl-3-methoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-methoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 345Example 345

9-Methyl-3-ethoxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-ethoxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 346Example 346

9-Methyl-3-propyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-methyl-3-propyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 347Example 347

9-Methyl-3-butyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-butyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 348Example 348

9-Methyl-3-pentyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-methyl-3-pentyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 349Example 349

9-Methyl-3-hexyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-hexyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 350Example 350

9-Methyl-3-heptyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthre-n9-methyl-3-heptyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthre-n

Beispiel 351Example 351

9-Methyl-3-octyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]­ phenanthren9-methyl-3-octyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 352Example 352

9-Methyl-3-nonyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren-9-methyl-3-nonyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 353Example 353

9-Methyl-3-decyloxy-4-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren- 9-methyl-3-decyloxy-4-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 354Example 354

9-Decyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren wird analog Beispiel 231, jedoch unter Verwendung von 1-Brom-2,3,4-trifluorbenzol hergestellt.9-Decyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene becomes analogous Example 231, but using 1-bromo-2,3,4-trifluorobenzene manufactured.

Analog Beispiel 354 werden erhalten:Analogously to Example 354, the following are obtained:

Beispiel 355Example 355

9-Nonyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 356Example 356

9-Octyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 357Example 357

9-Heptyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 358Example 358

9-Hexyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 359Example 359

9-Pentyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-pentyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 360Example 360

9-Butyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 361Example 361

9-Propyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 362Example 362

9-Ethyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 363Example 363

9-Methyl-2,3,4-trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 364Example 364

2,3,4-Trifluor-9,10-dihydro-8H-cyclopenta[b]phenanthren2,3,4-trifluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 365Example 365

9-Decyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren wird analog Beispiel 354 erhalten, jedoch unter Einsatz von 2,3-Difluorbrombenzol.9-Decyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene becomes analogous Example 354 obtained, but using 2,3-difluorobromobenzene.

Analog Beispiel 365 werden erhalten:Analogously to example 365, the following are obtained:

Beispiel 366Example 366

9-Nonyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 367Example 367

9-Octyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 368Example 368

9-Heptyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 369Example 369

9-Hexyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 370Example 370

9-Pentyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-pentyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 371Example 371

9-Butyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren 9-butyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene  

Beispiel 372Example 372

9-Propyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 373Example 373

9-Ethyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 374Example 374

9-Methyl-3,4-difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 375Example 375

3,4-Difluor-9,10-dihydro-8H-cyclopenta[b]phenanthren3,4-difluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 376Example 376

9-Decyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren wird analog Beispiel 365 erhalten, jedoch unter Verwendung von 3-Fluor-brombenzol.9-Decyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene is analogous to Example 365 obtained, but using 3-fluorobromobenzene.

Analog Beispiel 376 werden erhalten:Analogously to Example 376, the following are obtained:

Beispiel 377Example 377

9-Nonyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-nonyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 378Example 378

9-Octyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-octyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 379Example 379

9-Heptyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-heptyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 380Example 380

9-Hexyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-Hexyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 381Example 381

9-Pentyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-pentyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 382Example 382

9-Butyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-butyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 383Example 383

9-Propyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-propyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 384Example 384

9-Ethyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-ethyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 385Example 385

9-Methyl-3-fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren9-methyl-3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 386Example 386

3-Fluor-9,10-dihydro-8H-cyclopenta[b]phenanthren3-fluoro-9,10-dihydro-8H-cyclopenta [b] phenanthrene

Beispiel 387Example 387

3-Hexyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren wird analog Beispiel 1 aus 1-(6-Hexyloxy-pyridin-2-yl)ethin und 5-Brom-2-nonyl­ benzo[1,3]dioxol (hergestellt durch Umsetzung von 3,4-Methylendioxy­ brombenzol mit PCl₅ und sauer katalysierte Acetalisierung des so erhalten 4-Brom-brenzkatechins mit Decanal in siedendem Toluol) nach der beschriebenen Reaktionsfolge hergestellt. 3-Hexyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene becomes analogous Example 1 from 1- (6-hexyloxypyridin-2-yl) ethyne and 5-bromo-2-nonyl benzo [1,3] dioxole (made by reacting 3,4-methylenedioxy bromobenzene with PCl₅ and acid-catalyzed acetalization of the so obtained 4-bromo-catechins with decanal in boiling toluene) after reaction sequence described.  

Analog Beispiel 387 werden erhalten:Analogously to Example 387, the following are obtained:

Beispiel 388Example 388

3-Octyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-octyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 389Example 389

3-Heptyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-heptyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 390Example 390

3-Pentyloxy-9-nonyl-8,10-d ioxa-4-aza-cyclopenta[b]phenanthren3-pentyloxy-9-nonyl-8,10-d ioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 391Example 391

3-Butyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-butyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 392Example 392

3-Propyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b)phenanthren3-propyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b) phenanthrene

Beispiel 393Example 393

3-Ethyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-ethyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 394Example 394

3-Methyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-methyloxy-9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 395Example 395

9-Nonyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-nonyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 396Example 396

9-Octyl-8,10-dioxa-4-aza-cyclopenta(b]phenanthren9-octyl-8,10-dioxa-4-aza-cyclopenta (b] phenanthrene

Beispiel 397Example 397

9-Octyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 398Example 398

9-Octyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 399Example 399

9-Octyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 400Example 400

9-Octyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 401Example 401

9-Octyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 402Example 402

9-Octyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 403Example 403

9-Octyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 404Example 404

9-Octyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 405Example 405

9-Octyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 406Example 406

9-Octyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-octyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 407Example 407

9-Octyl-3-(6-methyl)octyloxy-8,10-dioxa-4-aza- cyclopenta[b]phenanthren9-octyl-3- (6-methyl) octyloxy-8,10-dioxa-4-aza- cyclopenta [b] phenanthrene

Beispiel 408Example 408

9-Octyl-3-(1-methyl)heptyloxy-8,10-dioxa-4-aza- cyclopenta[b]phenanthren9-octyl-3- (1-methyl) heptyloxy-8,10-dioxa-4-aza- cyclopenta [b] phenanthrene

Beispiel 409Example 409

9-Octyl-3-(6-cyclopropyl)hexyloxy-8,10-dioxa-4-aza­ cyclopenta[b]phenanthren9-octyl-3- (6-cyclopropyl) hexyloxy-8,10-dioxa-4-aza cyclopenta [b] phenanthrene

Beispiel 410Example 410

9-Octyl-3-[3-(pentyl-dimethylsilyl)]propyloxy-8,10-dioxa-4-aza- cyclopenta[b]phenanthren9-octyl-3- [3- (pentyl-dimethylsilyl)] propyloxy-8,10-dioxa-4-aza- cyclopenta [b] phenanthrene

Beispiel 412Example 412

9-Octyl-3-[(R)-2-fluor]octyloxy-8,10-dioxa-4-aza- cyclopenta(b]phenanthren 9-octyl-3 - [(R) -2-fluoro] octyloxy-8,10-dioxa-4-aza- cyclopenta (b] phenanthrene  

Beispiel 413Example 413

9-Octyl-3-(1H, 1H-perfluor-octyloxy)-8,10-dioxa-4-aza- cyclopenta[b]phenanthren9-octyl-3- (1H, 1H-perfluoro-octyloxy) -8,10-dioxa-4-aza- cyclopenta [b] phenanthrene

Beispiel 414Example 414

9-Heptyl-3-dodecyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-dodecyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 415Example 415

9-Heptyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 416Example 416

9-Heptyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 417Example 417

9-Heptyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 418Example 418

9-Heptyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 419Example 419

9-Heptyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 420Example 420

9-Heptyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 421Example 421

9-Heptyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 422Example 422

9-Heptyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 423Example 423

9-Heptyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 424Example 424

9-Heptyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 425Example 425

9-Heptyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 426Example 426

9-Heptyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-heptyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 427Example 427

9-Hexyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 428Example 428

9-Hexyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 429Example 429

9-Hexyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 430Example 430

9-Hexyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 431Example 431

9-Hexyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 432Example 432

9-Hexyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 433Example 433

9-Hexyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 434Example 434

9-Hexyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 435Example 435

9-Hexyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 436Example 436

9-Hexyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 437Example 437

9-Hexyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-Hexyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 438Example 438

9-Pentyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 439Example 439

9-Pentyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 440Example 440

9-Pentyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 441Example 441

9-Pentyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 442Example 442

9-Pentyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 443Example 443

9-Pentyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren 9-pentyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene  

Beispiel 444Example 444

9-Pentyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 445Example 445

9-Pentyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 446Example 446

9-Pentyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 447Example 447

9-Pentyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 448Example 448

9-Pentyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 449Example 449

9-Pentyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 450Example 450

9-Pentyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-pentyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 451Example 451

9-Butyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 452Example 452

9-Butyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 453Example 453

9-Butyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 454Example 454

9-Butyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 455Example 455

9-Butyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 456Example 456

9-Butyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 457Example 457

9-Butyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 458Example 458

9-Butyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 459Example 459

9-Butyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 460Example 460

9-Butyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 461Example 461

9-Butyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 462Example 462

9-Butyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 463Example 463

9-Butyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 464Example 464

9-Butyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-butyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 465Example 465

9-Propyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 466Example 466

9-Propyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 467Example 467

9-Propyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 468Example 468

9-Propyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 469Example 469

9-Propyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 470Example 470

9-Propyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 471Example 471

9-Propyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 472Example 472

9-Propyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 472Example 472

9-Propyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 473Example 473

9-Propyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 474Example 474

9-Propyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren 9-propyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene  

Beispiel 475Example 475

9-Propyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 476Example 476

9-Propyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-propyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 477Example 477

9-Ethyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-ethyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 478Example 478

9-Ethyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-dodecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 479Example 479

9-Ethyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 480Example 480

9-Ethyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 481Example 481

9-Ethyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 482Example 482

9-Ethyl-3-octyloxy-8,10-d ioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-octyloxy-8,10-d ioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 483Example 483

9-Ethyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 484Example 484

9-Ethyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 485Example 485

9-Ethyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 486Example 486

9-Ethyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 487Example 487

9-Ethyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 488Example 488

9-Ethyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 489Example 489

9-Ethyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenathren9-ethyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenathrene

Beispiel 490Example 490

9-Ethyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-ethyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 491Example 491

9-Methyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 492Example 492

9-Methyl-3-dodecyl-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-dodecyl-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 493Example 493

9-Methyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-undecyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 494Example 494

9-Methyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 496Example 496

9-Methyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 497Example 497

9-Methyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 498Example 498

9-Methyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 499Example 499

9-Methyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 500Example 500

9-Methyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 501Example 501

9-Methyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 502Example 502

9-Methyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 503Example 503

9-Methyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 504Example 504

9-Methyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren9-methyl-3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 505Example 505

8,10-Dioxa-4-aza-cyclopenta[b]phenanthren8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 506Example 506

3-Decyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-decyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 507Example 507

3-Nonyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren 3-nonyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene  

Beispiel 508Example 508

3-Octyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-octyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 509Example 509

3-Heptyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-heptyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 510Example 510

3-Hexyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-Hexyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 511Example 511

3-Pentyloxy-8,10-dioxa-4-aza-cyclopenta[b)phenanthren3-pentyloxy-8,10-dioxa-4-aza-cyclopenta [b) phenanthrene

Beispiel 512Example 512

3-Butyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-butyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 513Example 513

3-Propyloxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-propyloxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 514Example 514

3-Ethoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-ethoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 515Example 515

3-Methoxy-8,10-dioxa-4-aza-cyclopenta[b]phenanthren3-methoxy-8,10-dioxa-4-aza-cyclopenta [b] phenanthrene

Beispiel 516Example 516

9-Nonyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol wird analog Beispiel 387 aus 3-Hexyloxy-brombenzol und 5-Brom-2-nonyl-benzo[1,3]dioxol erhalten.9-Nonyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole is produced analogously to Example 387 3-Hexyloxy-bromobenzene and 5-bromo-2-nonyl-benzo [1,3] dioxole obtained.

Analog Beispiel 516 werden erhalten:Analogously to Example 516, the following are obtained:

Beispiel 517Example 517

9-Nonyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 518Example 518

9-Nonyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 519Example 519

9-Nonyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 520Example 520

9-Nonyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 521Example 521

9-Nonyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 522Example 522

9-Nonyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 523Example 523

9-Nonyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 524Example 524

9-Nonyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 525Example 525

9-Nonyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 526Example 526

9-Nonyl-phenanthro[2,3-d][1,3]dioxol9-nonylphenanthro [2,3-d] [1,3] dioxole

Beispiel 527Example 527

9-Octyl-phenanthro[2,3-d][1,3]dioxol9-octylphenanthro [2,3-d] [1,3] dioxole

Beispiel 528Example 528

9-Octyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 529Example 529

9-Octyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 530Example 530

9-Octyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 531Example 531

9-Octyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 532Example 532

9-Octyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol 9-octyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole  

Beispiel 533Example 533

9-Octyl-3-pentyloxyphenanthro[2,3-d][1,3]dioxol9-octyl-3-pentyloxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 534Example 534

9-Octyl-3-butyloxy-phenanthro[2,3-d1[1,3]dioxol9-octyl-3-butyloxy-phenanthro [2,3-d1 [1,3] dioxole

Beispiel 535Example 535

9-Octyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 536Example 536

9-Octyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 537Example 537

9-Octyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-octyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 538Example 538

9-Octyl-phenanthro[2,3-d][1,3]dioxol9-octylphenanthro [2,3-d] [1,3] dioxole

Beispiel 539Example 539

9-Heptyl-phenanthro[2,3-d][1,3]dioxol9-heptylphenanthro [2,3-d] [1,3] dioxole

Beispiel 540Example 540

9-Heptyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 541Example 541

9-Heptyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 542Example 542

9-Heptyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 543Example 543

9-Heptyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 544Example 544

9-Heptyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 545Example 545

9-Heptyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 546Example 546

9-Heptyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 547Example 547

9-Heptyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 548Example 548

9-Heptyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 549Example 549

9-Heptyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 550Example 550

9-Heptyl-3-(6-methyl)octyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3- (6-methyl) octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 551Example 551

9-Heptyl-3-(1-methyl)heptyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3- (1-methyl) heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 552Example 552

9-Heptyl-3-(8-cyclopropyl)octyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3- (8-cyclopropyl) octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 553Example 553

9-Heptyl-3-[5-(Butyl-dimethylsilyl)]pentyloxy-phenanthin[2,3- d][1,3]dioxol9-heptyl-3- [5- (butyldimethylsilyl)] pentyloxyphenanthine [2,3- d] [1,3] dioxole

Beispiel 554Example 554

9-Heptyl-3-[(R)-2-fluor]hexyloxy-phenanthro[2,3-d][1,3]dioxol9-heptyl-3 - [(R) -2-fluoro] hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 555Example 555

9-Heptyl-3-(1H,1H-perfluor-octyloxy)-phenanthro[2,3-d][1,3]dioxol9-heptyl-3- (1H, 1H-perfluoro-octyloxy) phenanthro [2,3-d] [1,3] dioxole

Beispiel 556Example 556

9-Hexyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 557Example 557

9-Hexyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 558Example 558

9-Hexyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 559Example 559

9-Hexyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 560Example 560

9-Hexyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 561Example 561

9-Hexyl-3-pentyloxyphenanthro[2,3-d][1,3]dioxol9-Hexyl-3-pentyloxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 562Example 562

9-Hexyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 563Example 563

9-Hexyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol 9-Hexyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole  

Beispiel 564Example 564

9-Hexyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-hexyl-3-ethoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 565Example 565

9-Hexyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 566Example 566

9-Hexyl-phenanthro[2,3-d][1,3]dioxol9-hexylphenanthro [2,3-d] [1,3] dioxole

Beispiel 567Example 567

9-Pentyl-phenanthro[2,3-d][1,3]dioxol9-pentylphenanthro [2,3-d] [1,3] dioxole

Beispiel 568Example 568

9-Pentyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 569Example 569

9-Pentyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 570Example 570

9-Pentyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 571Example 571

9-Pentyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 572Example 572

9-Pentyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 573Example 573

9-Pentyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 574Example 574

9-Pentyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 575Example 575

9-Pentyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 576Example 576

9-Pentyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-ethoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 577Example 577

9-Pentyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 578Example 578

9-Butyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 579Example 579

9-Butyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 580Example 580

9-Butyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 581Example 581

9-Butyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 582Example 582

9-Butyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 583Example 583

9-Butyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 584Example 584

9-Butyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 585Example 585

9-Butyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 586Example 586

9-Butyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-ethoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 587Example 587

9-Butyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-butyl-3-methoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 588Example 588

9-Butyl-phenanthro[2,3-d][1,3]dioxol9-butylphenanthro [2,3-d] [1,3] dioxole

Beispiel 589Example 589

9-Propyl-phenanthro[2,3-d][1,3]dioxol9-propylphenanthro [2,3-d] [1,3] dioxole

Beispiel 590Example 590

9-Propyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 591Example 591

9-Propyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 592Example 592

9-Propyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 593Example 593

9-Propyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 594Example 594

9-Propyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 595Example 595

9-Propyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol 9-propyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole  

Beispiel 596Example 596

9-Propyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 597Example 597

9-Propyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 598Example 598

9-Propyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 599Example 599

9-Propyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-propyl-3-methoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 600Example 600

9-Ethyl-3-decyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 601Example 601

9-Ethyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 602Example 602

9-Ethyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 603Example 603

9-Ethyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 604Example 604

9-Ethyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 605Example 605

9-Ethyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 606Example 606

9-Ethyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 607Example 607

9-Ethyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 608Example 608

9-Ethyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 609Example 609

9-Ethyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 610Example 610

9-Ethyl-phenanthro[2,3-d][1,3]dioxol9-ethylphenanthro [2,3-d] [1,3] dioxole

Beispiel 612Example 612

9-Methyl-phenanthro(2,3-d][1,3]dioxol9-methylphenanthro (2,3-d] [1,3] dioxole

Beispiel 613Example 613

9-Methyl-decyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 614Example 614

9-Methyl-3-nonyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 615Example 615

9-Methyl-3-octyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 616Example 616

9-Methyl-3-heptyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-heptyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 617Example 617

9-Methyl-3-hexyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 618Example 618

9-Methyl-3-pentyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-pentyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 619Example 619

9-Methyl-3-butyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 620Example 620

9-Methyl-3-propyloxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 621Example 621

9-Methyl-3-ethoxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 622Example 622

9-Methyl-3-methoxy-phenanthro[2,3-d][1,3]dioxol9-methyl-3-methoxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 623Example 623

Phenanthro[2,3-d][1,3]dioxolPhenanthro [2,3-d] [1,3] dioxole

Beispiel 624Example 624

3-Decyloxy-phenanthro[2,3-d][1,3]dioxol3-decyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 625Example 625

3-Nonyloxy-phenanthro[2,3-d][1,3]dioxol3-nonyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 626Example 626

3-Octyloxy-phenanthro[2,3-d][1,3]dioxol3-octyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 627Example 627

3-Heptyloxy phenanthro[2,3-d][1,3]dioxol3-heptyloxy phenanthro [2,3-d] [1,3] dioxole

Beispiel 628Example 628

3-Hexyloxy-phenanthro[2,3-d][1,3]dioxol 3-hexyloxy-phenanthro [2,3-d] [1,3] dioxole  

Beispiel 629Example 629

3-Pentyloxy-phenanthro[2,3-d][1,3]dioxol3-pentyloxyphenanthro [2,3-d] [1,3] dioxole

Beispiel 630Example 630

3-Butyloxy-phenanthro[2,3-d][1,3]dioxol3-butyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 631Example 631

3-Propyloxy-phenanthro[2,3-d][1,3]dioxol3-propyloxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 632Example 632

3-Ethoxy-phenanthro[2,3-d][1,3]dioxol3-ethoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 633Example 633

3-Methoxy-phenanthro[2,3-d][1,3]dioxol3-methoxy-phenanthro [2,3-d] [1,3] dioxole

Beispiel 634Example 634

9-Nonyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol wird analog Beispiel 516 aus 2-Fluor-3-decyloxy-brombenzol und 5-Brom-2-nonyl-benzo[1,3]dioxol erhalten.9-Nonyl-3-decyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole becomes analogous to example 516 from 2-fluoro-3-decyloxy-bromobenzene and 5-bromo-2-nonyl-benzo [1,3] dioxole receive.

Analog Beispiel 634 werden erhalten:Analogously to Example 634, the following are obtained:

Beispiel 635Example 635

9-Nonyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 636Example 636

9-Nonyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 637Example 637

9-Nonyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 638Example 638

9-Nonyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-hexyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 639Example 639

9-Nonyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 640Example 640

9-Nonyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 641Example 641

9-Nonyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 642Example 642

9-Nonyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 643Example 643

9-Nonyl-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 644Example 644

9-Nonyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-nonyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 645Example 645

9-Octyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 646Example 646

9-Octyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-nonyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 647Example 647

9-Octyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-decyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 648Example 648

9-Octyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-nonyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 649Example 649

9-Octyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 650Example 650

9-Octyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 651Example 651

9-Octyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-hexyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 652Example 652

9-Octyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol 9-octyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole  

Beispiel 653Example 653

9-Octyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-butyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 654Example 654

9-Octyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 655Example 655

9-Octyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 656Example 656

9-Octyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-octyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 657Example 657

9-Heptyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-decyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 658Example 658

9-Heptyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 659Example 659

9-Heptyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-octyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 660Example 660

9-Heptyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 661Example 661

9-Heptyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-hexyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 662Example 662

9-Heptyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 663Example 663

9-Heptyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-butyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 664Example 664

9-Heptyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-propyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 665Example 665

9-Heptyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 666Example 666

9-Heptyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-3-methoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 667Example 667

9-Heptyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-heptyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 668Example 668

9-Hexyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 669Example 669

9-Hexyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-decyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 670Example 670

9-Hexyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-nonyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 671Example 671

9-Hexyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 672Example 672

9-Hexyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 673Example 673

9-Hexyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-hexyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 674Example 674

9-Hexyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 675Example 675

9-Hexyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 676Example 676

9-Hexyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 677Example 677

9-Hexyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 678Example 678

9-Hexyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 679Example 679

9-Hexyl-3-(6-methyl)octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3- (6-methyl) octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 680Example 680

9-Hexyl-3-(1-methyl)heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-Hexyl-3- (1-methyl) heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 681Example 681

9-Hexyl-3-(8-cyclopropyl)octyloxy-4-fluor-phenanthro[2,3-d][1,3]diox-ol9-Hexyl-3- (8-cyclopropyl) octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] diox-ol

Beispiel 682Example 682

9-Hexyl-3-[5-(Butyl-dimethylsilyl)]pentyloxy-4-fluor-phenanthro- [2,3-d][1,3]dioxol 9-hexyl-3- [5- (butyldimethylsilyl)] pentyloxy-4-fluorophenanthro- [2,3-d] [1,3] dioxole  

Beispiel 683Example 683

9-Hexyl-3-[(R)-2-fluor]hexyloxy-4-fluor-phenanthro[2,-d][1,3]dioxol9-Hexyl-3 - [(R) -2-fluoro] hexyloxy-4-fluoro-phenanthro [2, -d] [1,3] dioxole

Beispiel 684Example 684

9-Hexyl-3-(1H,1H-perfluor-octyloxy)-4-fluor-phenanthro- [2,3-d][1,3]dioxol9-hexyl-3- (1H, 1H-perfluoro-octyloxy) -4-fluorophenanthro- [2,3-d] [1,3] dioxole

Beispiel 685Example 685

9-Pentyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-decyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 686Example 686

9-Pentyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-nonyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 687Example 687

9-Pentyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 688Example 688

9-Pentyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 689Example 689

9-Pentyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-hexyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 690Example 690

9-Pentyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 691Example 691

9-Pentyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 692Example 692

9-Pentyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 693Example 693

9-Pentyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 694Example 694

9-Pentyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-pentyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 695Example 695

9-Pentyl-4-fluor-phenanthro[2,3][1,3]dioxol9-pentyl-4-fluorophenanthro [2,3] [1,3] dioxole

Beispiel 696Example 696

9-Butyl-4-fluor-phenanthro[2,3][1,3]dioxol9-butyl-4-fluorophenanthro [2,3] [1,3] dioxole

Beispiel 697Example 697

9-Butyl-3-decyloxy-4-fluor-phenanthro[2,3][1,3]dioxol9-butyl-3-decyloxy-4-fluoro-phenanthro [2,3] [1,3] dioxole

Beispiel 698Example 698

9-Butyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 699Example 699

9-Butyl-3-octyloxy-4-fluor-phenanthro[2,3-d]1,3]dioxol9-butyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] 1,3] dioxole

Beispiel 700Example 700

9-Butyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 701Example 701

9-Butyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol < 04204 00070 552 001000280000000200012000285910409300040 0002004432970 00004 04085HE1<Beispiel 7029-butyl-3-hexyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole <04204 00070 552 001000280000000200012000285910409300040 0002004432970 00004 04085HE1 <Example 702

9-Butyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 703Example 703

9-Butyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 704Example 704

9-Butyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 705Example 705

9-Butyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 706Example 706

9-Butyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-butyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 707Example 707

9-Propyl-3-decyloxy-4-fluor-phenanthro[2,3][1,3]dioxol9-propyl-3-decyloxy-4-fluoro-phenanthro [2,3] [1,3] dioxole

Beispiel 708Example 708

9-Propyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 709Example 709

9-Propyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 710Example 710

9-Propyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 711Example 711

9-Propyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-hexyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 712Example 712

9-Propyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 713Example 713

9-Propyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol 9-propyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole  

Beispiel 714Example 714

9-Propyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-propyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 715Example 715

9-Propyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 716Example 716

9-Propyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 717Example 717

9-Propyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-propyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 718Example 718

9-Ethyl-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 719Example 719

9-Ethyl-3-decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-decyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 720Example 720

9-Ethyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 721Example 721

9-Ethyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 722Example 722

9-Ethyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 723Example 723

9-Ethyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-hexyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 724Example 724

9-Ethyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 725Example 725

9-Ethyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-butyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 726Example 726

9-Ethyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-propyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 727Example 727

9-Ethyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 728Example 728

9-Ethyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-ethyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 729Example 729

9-Methyl-3-decyloxy-4-fluor-phenanthren[2,3-d][1,3]dioxol9-methyl-3-decyloxy-4-fluorophenanthrene [2,3-d] [1,3] dioxole

Beispiel 730Example 730

9-Methyl-3-nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 731Example 731

9-Methyl-3-octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-octyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 732Example 732

9-Methyl-3-heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-heptyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 733Example 733

9-Methyl-3-hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-hexyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 734Example 734

9-Methyl-3-pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 735Example 735

9-Methyl-3-butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-butyloxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 736Example 736

9-Methyl-3-propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-propyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 737Example 737

9-Methyl-3-ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-ethoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 738Example 738

9-Methyl-3-methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol9-methyl-3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 739Example 739

9-Methyl-4-fluor-phenanthro[2,3-][1,3]dioxol9-methyl-4-fluoro-phenanthro [2,3 -] [1,3] dioxole

Beispiel 740Example 740

4-Fluor-phenanthro[2,3][1,3]dioxol4-fluoro-phenanthro [2,3] [1,3] dioxole

Beispiel 741Example 741

3-Decyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-decyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 742Example 742

3-Nonyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-nonyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 743Example 743

3-Octyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-octyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 744Example 744

3-Heptyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-heptyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 745Example 745

3-Hexyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol 3-Hexyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole  

Beispiel 746Example 746

3-Pentyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-pentyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 747Example 747

3-Butyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-butyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 748Example 748

3-Propyloxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-propyloxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Beispiel 749Example 749

3-Ethoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-ethoxy-4-fluoro-phenanthro [2,3-d] [1,3] dioxole

Beispiel 750Example 750

3-Methoxy-4-fluor-phenanthro[2,3-d][1,3]dioxol3-methoxy-4-fluorophenanthro [2,3-d] [1,3] dioxole

Claims (10)

1. Tetracyclische Verbindungen der Formel (I), wobei die Symbole und Indizes folgende Bedeutungen haben:
R¹: ist H, CN, F, Cl, CF₃, ein geradkettiger oder verzweigter Alkylrest (mit oder ohne asymmetrisches C-Atom) mit 1 bis 20 C-Atomen, wobei auch eine oder mehrere CH₂-Gruppen durch -O-, -S-, -C(=O)-, -CH=CH-, -C-C-, Cyclopropan-1,2-diyl, -Si(CH₃)₂-, 1,4- Phenylen, 1,4-Cyclohexylen, 1,3-Cyclopentylen, 1,3-Cyclobutylen ersetzt sein können, mit der Maßgabe, daß Sauerstoffatome und/oder Schwefelatome nicht unmittelbar miteinander gebunden sein dürfen, und/oder wobei ein oder mehrere H-Atome des Alkylrestes durch -F, -Cl, -Br oder -OR³ substituiert sein können, oder auch eine der nachfolgenden Gruppen (optisch aktiv oder racemisch): R²: ist H oder ein geradkettiger oder verzweigter Alkylrest mit 1 bis 20 C-Atomen (mit oder ohne asymmetrisches C-Atom), wobei auch eine oder mehrere CH₂-Gruppen (jedoch nicht die unmittelbar an den Ring D gebundene) durch -O-, -S-, -CH=CH-, -C-C-, Cyclopropan-1,2-diyl, -Si(CH₃)₂-, -C(=O)-, 1,4-Phenylen, 1,4- Cyclohexylen, 1,3-Cyclopentylen, 1,3-Cyclobutylen, 1,3-Dioxan- 2,5-diyl ersetzt sein können mit der Maßgabe, daß Sauerstoffatome und Schwefelatome nicht direkt miteinander verbunden sein dürfen, und/oder ein oder mehrere H-Atome des Alkylrestes durch -F, -Cl, -Br oder -OR³ substituiert sein können;
R³: ist H oder ein geradkettiger Alkylrest mit 1 bis 6 C-Atomen;
R⁴, R⁵, R⁶: sind gleich oder verschieden Wasserstoff oder ein geradkettiger oder verzweigter Alkylrest mit 1-16 C-Atomen, wobei auch eine oder zwei CH₂-Gruppen durch -O- und/oder -CH = CH- ersetzt sein können, mit der Maßgabe, daß Sauerstoffatome nicht unmittelbar miteinander gebunden sein dürfen, R⁴ und R⁵ können zusammen auch -(CH₂)₄- oder -(CH₂)₅- sein, wenn sie an ein Oxiran-, Dioxolan-, Tetrahydrofuran-, Tetrahydropyran-, Bytorolacton- oder Valerolacton-System gebunden sind;
A¹: ist (gegebenenfalls durch 1 bis 3 F-Atome substituiertes) 1,4- Phenylen, 1,4-Cyclohexylen, Pyridin-2,5-diyl (ggf. α zum N-Atom durch F substituiert), Pyrimidin-2,5-diyl oder (1,3,4)-Thiadiazol-2,5- diyl;
M¹: ist eine Einfachbindung, -CH₂CH₂-, -C-C-, -O-CO-, -CO-O-, -O-CH₂-, CH₂-O oder -O-CO-O-;
Q¹: ist -CO-O- oder -CH₂-O- oder eine Einfachbindung
m: Null oder Eins;
Ring A: ist Ring C: ist Ring D: ist B¹, B²: sind -CH=CH-, -CH=N-, -N=CH-, -CH₂CH₂-, -CH₂O-, -OCH₂-, -O-CO-, -CO-O;
k, n: sind Null oder 1;
mit der Maßgabe, daß die Summe aus k und n = 1 sein muß.1. tetracyclic compounds of the formula (I), where the symbols and indices have the following meanings:
R¹: is H, CN, F, Cl, CF₃, a straight-chain or branched alkyl radical (with or without an asymmetric carbon atom) with 1 to 20 carbon atoms, one or more CH₂ groups by -O-, -S -, -C (= O) -, -CH = CH-, -CC-, cyclopropane-1,2-diyl, -Si (CH₃) ₂-, 1,4-phenylene, 1,4-cyclohexylene, 1, 3-cyclopentylene, 1,3-cyclobutylene can be replaced, with the proviso that oxygen atoms and / or sulfur atoms must not be bonded directly to one another, and / or one or more H atoms of the alkyl radical being used by -F, -Cl, - Br or -OR³ can be substituted, or one of the following groups (optically active or racemic): R²: is H or a straight-chain or branched alkyl radical having 1 to 20 C atoms (with or without an asymmetrical C atom), one or more CH 2 groups (but not the one directly bonded to the ring D) also being -O- , -S-, -CH = CH-, -CC-, cyclopropane-1,2-diyl, -Si (CH₃) ₂-, -C (= O) -, 1,4-phenylene, 1,4-cyclohexylene , 1,3-cyclopentylene, 1,3-cyclobutylene, 1,3-dioxane-2,5-diyl can be replaced with the proviso that oxygen atoms and sulfur atoms must not be directly connected to one another, and / or one or more H- Atoms of the alkyl radical can be substituted by -F, -Cl, -Br or -OR³;
R³: is H or a straight-chain alkyl radical with 1 to 6 C atoms;
R⁴, R⁵, R⁶: are identical or different hydrogen or a straight-chain or branched alkyl radical having 1-16 C atoms, where one or two CH₂ groups can be replaced by -O- and / or -CH = CH- with the proviso that oxygen atoms must not be bonded directly to one another, R⁴ and R⁵ together can also be - (CH₂) ₄- or - (CH₂) ₅- if they are an oxirane, dioxolane, tetrahydrofuran, tetrahydropyran, bytorolactone - or valerolactone system are bound;
A¹: is (optionally substituted by 1 to 3 F atoms) 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl (optionally α to the N atom by F), pyrimidine-2, 5-diyl or (1,3,4) thiadiazole-2,5-diyl;
M¹: is a single bond, -CH₂CH₂-, -CC-, -O-CO-, -CO-O-, -O-CH₂-, CH₂-O or -O-CO-O-;
Q¹: is -CO-O- or -CH₂-O- or a single bond
m: zero or one;
Ring A: is Ring C: is Ring D: is B¹, B²: are -CH = CH-, -CH = N-, -N = CH-, -CH₂CH₂-, -CH₂O-, -OCH₂-, -O-CO-, -CO-O;
k, n: are zero or 1;
with the proviso that the sum of k and n must be = 1. 2. Tetracyclische Verbindungen der Formel (I) nach Anspruch 1, gekennzeichnet durch die Formeln (Ia) und (Ib), wobei Ring A: bedeutet
und die übrigen Symbole und Indizes die in Formel (I) in Anspruch 1 angegebenen Bedeutungen haben.2. tetracyclic compounds of formula (I) according to claim 1, characterized by the formulas (Ia) and (Ib), where ring A: means
and the other symbols and indices have the meanings given in formula (I) in claim 1. 3. Tetracyclische Verbindungen der Formel (I) nach Anspruch 1 und/oder 2, gekennzeichnet durch die Formeln (Ia1) bis (Ia12) und (Ib1) bis (Ib12), wobei die Reste R¹ und R² die in Formel (I) in Anspruch 1 angegebenen Bedeutungen haben.3. tetracyclic compounds of formula (I) according to claim 1 and / or 2, characterized by the formulas (Ia1) to (Ia12) and (Ib1) to (Ib12), wherein the radicals R¹ and R² have the meanings given in formula (I) in claim 1. 4. Verwendung von tetracyclischen Verbindungen der Formel (I) nach einem oder mehreren der Ansprüche 1 bis 3 als Komponenten von Flüssigkristallmischungen.4. Use of tetracyclic compounds of formula (I) according to one or more of claims 1 to 3 as components of Liquid crystal mixtures. 5. Flüssigkristallmischung, enthaltend mindestens eine Verbindung der Formel (I) nach einem oder mehreren der Ansprüche 1 bis 3. 5. Liquid crystal mixture containing at least one compound of Formula (I) according to one or more of claims 1 to 3.   6. Flüssigkristallmischung nach Anspruch 5, enthaltend 1 bis 8 Verbindungen der Formel (I).6. A liquid crystal mixture according to claim 5, containing 1 to 8 Compounds of formula (I). 7. Flüssigkristallmischung nach Anspruch 5 und/oder 6, dadurch gekennzeichnet, daß die Flüssigkristallmischung ferroelektrisch ist.7. Liquid crystal mixture according to claim 5 and / or 6, characterized characterized in that the liquid crystal mixture is ferroelectric. 8. Flüssigkristallmischung nach Anspruch 5 und/oder 6, dadurch gekennzeichnet, daß die Flüssigkristallmischung nematisch ist.8. Liquid crystal mixture according to claim 5 and / or 6, characterized characterized in that the liquid crystal mixture is nematic. 9. Flüssigkristallmischung nach Anspruch 4 oder 5, dadurch gekennzeichnet, daß sie 0,1 bis 70 Mol.-% an mindestens einer Verbindung der Formel (I) in Anspruch 1 enthält.9. Liquid crystal mixture according to claim 4 or 5, characterized in that that they 0.1 to 70 mol .-% of at least one compound of formula (I) in Claim 1 contains. 10. Schalt- und/oder Anzeigevorrichtung, enthaltend Trägerplatten, Elektroden, mindestens einen Polarisator, mindestens eine Orientierungsschicht sowie ein flüssigkristallines Medium, dadurch gekennzeichnet, daß das flüssigkristalline Medium eine Flüssigkristallmischung nach einem oder mehreren der Ansprüche 5 bis 9 ist.10. Switching and / or display device containing carrier plates, Electrodes, at least one polarizer, at least one orientation layer and a liquid-crystalline medium, characterized in that the liquid crystalline medium a liquid crystal mixture according to one or more of claims 5 to 9.
DE4432970A 1994-09-16 1994-09-16 New tetra:cyclic cpds., e.g. cyclo:alkyl:phenanthrene derivs. Withdrawn DE4432970A1 (en)

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WO1999024385A1 (en) * 1997-11-05 1999-05-20 Aventis Research & Technologies Gmbh & Co. Kg Fluorinated derivatives of phenanthrene and the utilization thereof in liquid crystal mixtures
DE10140148B4 (en) * 2001-08-16 2012-07-19 Merck Patent Gmbh Fluorinated polycycles and their use in liquid crystal mixtures and in liquid crystal displays
CN108865175A (en) * 2018-05-24 2018-11-23 西安瑞立电子材料有限公司 A kind of liquid-crystal composition containing two furans of dibenzo and its application
CN108865177A (en) * 2018-08-13 2018-11-23 西安瑞立电子材料有限公司 Liquid crystal media and application in a liquid crystal display
CN109536182A (en) * 2018-12-19 2019-03-29 西安瑞立电子材料有限公司 Liquid-crystal compounds, liquid crystal media and application
CN111218290A (en) * 2019-12-27 2020-06-02 Tcl华星光电技术有限公司 Liquid crystal molecule and liquid crystal display panel

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024385A1 (en) * 1997-11-05 1999-05-20 Aventis Research & Technologies Gmbh & Co. Kg Fluorinated derivatives of phenanthrene and the utilization thereof in liquid crystal mixtures
US6482478B1 (en) 1997-11-05 2002-11-19 Aventis Research & Technologies Gmbh & Co. Kg Fluorinated derivatives of phenanthrene and the utilization thereof in liquid crystal mixtures
DE10140148B4 (en) * 2001-08-16 2012-07-19 Merck Patent Gmbh Fluorinated polycycles and their use in liquid crystal mixtures and in liquid crystal displays
CN108865175A (en) * 2018-05-24 2018-11-23 西安瑞立电子材料有限公司 A kind of liquid-crystal composition containing two furans of dibenzo and its application
CN108865175B (en) * 2018-05-24 2020-05-15 石家庄晶奥量新材料有限公司 Liquid crystal composition containing dibenzofuran and application thereof
CN108865177A (en) * 2018-08-13 2018-11-23 西安瑞立电子材料有限公司 Liquid crystal media and application in a liquid crystal display
CN108865177B (en) * 2018-08-13 2020-06-09 石家庄晶奥量新材料有限公司 Liquid-crystalline medium and use in liquid-crystal displays
CN109536182A (en) * 2018-12-19 2019-03-29 西安瑞立电子材料有限公司 Liquid-crystal compounds, liquid crystal media and application
CN111218290A (en) * 2019-12-27 2020-06-02 Tcl华星光电技术有限公司 Liquid crystal molecule and liquid crystal display panel

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