DE3814346A1 - PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME - Google Patents

PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME

Info

Publication number
DE3814346A1
DE3814346A1 DE3814346A DE3814346A DE3814346A1 DE 3814346 A1 DE3814346 A1 DE 3814346A1 DE 3814346 A DE3814346 A DE 3814346A DE 3814346 A DE3814346 A DE 3814346A DE 3814346 A1 DE3814346 A1 DE 3814346A1
Authority
DE
Germany
Prior art keywords
trans
pyridin
ester
carboxylic acid
ethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
DE3814346A
Other languages
German (de)
Inventor
Andreas Dr Waechtler
Joachim Dr Krause
Volker Reiffenrath
Ulrich Dr Finkenzeller
Thomas Dr Geelhaar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to DE3814346A priority Critical patent/DE3814346A1/en
Priority to JP1504480A priority patent/JPH02504035A/en
Priority to PCT/EP1989/000408 priority patent/WO1989010356A1/en
Priority to EP89904791A priority patent/EP0365641A1/en
Priority to CN89102622A priority patent/CN1037334A/en
Priority to DD89327988A priority patent/DD283833A5/en
Publication of DE3814346A1 publication Critical patent/DE3814346A1/en
Priority to KR1019890702461A priority patent/KR900700453A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine

Abstract

Compounds of formula (I), wherein A denotes a pyridine ring, are particularly useful as components of liquid-crystal.

Description

Pyridinderivate, ihre Verwendung als Komponenten flüssig­ kristalliner Phasen, entsprechende Flüssigkristallphasen und sie enthaltende FlüssigkristallanzeigeelementePyridine derivatives, their use as liquid components crystalline phases, corresponding liquid crystal phases and liquid crystal display elements containing them

Die Erfindung betrifft Pyridinderivate der Formel IThe invention relates to pyridine derivatives of the formula I.

worin
R¹ und R² jeweils unabhängig voneinander einen Alkylrest mit 1-15 C-Atomen oder einen Alkenylrest mit 2-15 C-Atomen, wobei in diesen Resten auch eine CH₂-Gruppe durch -O-, -CO-, -O-CO- oder -CO-O- ersetzt sein kann,wherein
R¹ and R² each independently an alkyl radical with 1-15 C atoms or an alkenyl radical with 2-15 C atoms, in which radicals a CH₂ group by -O-, -CO-, -O-CO- or -CO-O- can be replaced,

Z¹ -CH₂-CH₂- oder eine Einfachbindung,
A¹ -O-CO-Phe-,
Phe unsubstituiertes oder ein- oder mehrfach durch F- und/oder Cl-Atome und/oder CH₃- und/oder CN-Gruppen substituiertes 1,4- Phenylen,
n 0 oder 1
und
m 0 oder 1
bedeutet,
mit der Maßgabe, daß im FalleZ¹ -CH₂-CH₂- or a single bond,
A¹ -O-CO-Phe-,
Phe 1,4-phenylene which is unsubstituted or mono- or polysubstituted by F and / or Cl atoms and / or CH₃ and / or CN groups,
n 0 or 1
and
m 0 or 1
means
with the proviso that in the case

R² = -O-COAlkyl und/oder m = 1 und/oder
Z¹ = -CH₂CH₂- ist.R² = -O-COalkyl and / or m = 1 and / or
Z¹ = -CH₂CH₂- is.

sowie die Verwendung dieser Verbindungen als Komponenten flüssigkristalliner Phasen, entsprechende Flüssigkristallphasen und sie enthaltende Flüssigkristallanzeigeelemente.and the use of these compounds as components liquid crystalline phases, corresponding liquid crystal phases and liquid crystal display elements containing them.

Der Einfachheit halber bedeuten im folgenden Cyc eine 1,4-Cyclohexylengruppe, Phe eine 1,4-Phenylengruppe und PheX eine durch F- und/oder Cl-Atome und/oder CH₃- und/oder CN-Gruppen ein- oder mehrfach substituierte 1,4- Phenylengruppe.For the sake of simplicity, Cyc in the following means one 1,4-cyclohexylene group, Phe a 1,4-phenylene group and PheX one by F and / or Cl atoms and / or CH₃- and / or CN groups mono- or polysubstituted 1,4- Phenylene group.

Die Verbindungen der Formel I können wie ähnliche Verbindungen als Komponenten flüssigkristalliner Phasen verwendet werden, insbesondere für Displays, die auf dem Prinzip der verdrillten Zelle (TN-Displays), dem Guest-Hoest-Effekt, dem ECB-Effekt, dem Effekt der Deformation aufgerichteter Phasen, dem Effekt der dynamischen Streuung oder dem SSFLC-Prinzip beruhen, oder auch für TFT- oder STN-Mischungen. Für hochinformative Flüssigkristall-Anzeigeelemente mit besonders kurzen Schaltzeiten werden flüssigkristalline Phasen benötigt, die sehr niedrige Viskositäten und besonders vorteilhafte elastische Konstanten aufweisen.The compounds of formula I can be like similar compounds used as components of liquid crystalline phases , especially for displays based on the principle of twisted cell (TN displays), the guest hoest effect, the ECB effect, the effect of the deformation straightened up Phases, the effect of dynamic scattering or SSFLC principle, or also for TFT or STN mixtures.  For highly informative liquid crystal display elements with particularly short switching times, they become liquid crystalline Phases needed that very low viscosities and particularly advantageous elastic constants exhibit.

Der Erfindung lag die Aufgabe zugrunde, neue stabile flüssigkristalline oder mesogene Verbindungen aufzufinden, die als Komponenten flüssigkristalliner Phasen geeignet sind.The invention was based, new stable task find liquid-crystalline or mesogenic compounds, the as components of liquid crystalline phases are suitable.

Es wurde gefunden, daß die Verbindungen der Formel I als Komponenten flüssigkristalliner Phasen vorzüglich geeignet sind. Insbesondere sind mit der Hilfe stabile flüssigkristalline Phasen für hochinformative Displays mit kurzen Schaltzeiten herstellbar. Ferner eignen sich bestimmte Verbindungen der Formel I, auch als Komponenten ferroelektrischer Flüssigkristallphasen beispielsweise für Displays nach dem SSFLC-Prinzip.It has been found that the compounds of the formula I excellent as components of liquid crystalline phases are suitable. In particular, are stable with the help liquid crystalline phases for high information displays can be produced with short switching times. Are also suitable certain compounds of formula I, also as components ferroelectric liquid crystal phases for example for displays based on the SSFLC principle.

Mit der Bereitstellung der Verbindungen der Formel I wird außerdem ganz allgemein die Palette der flüssigkristallinen Substanzen, die sich unter verschiedenen anwendungstechnischen Gesichtspunkten zur Herstellung flüssigkristalliner Gemische eignen, erheblich ver­ breitert.With the provision of the compounds of formula I is also generally the range of liquid crystalline Substances that are different application aspects for manufacturing liquid crystalline mixtures are suitable, ver broadens.

Die Verbindungen der Formel I besitzen einen breiten Anwendungsbereich. In Abhängigkeit von der Auswahl der Substituenten können die Verbindungen als Basismaterialien dienen, aus denen flüssigkristalline Phasen zum überwiegenden Teil zusammengesetzt sind; es können aber auch Verbindungen der Formel I flüssigkristallinen Basismaterialien aus anderen Verbindungsklassen zugesetzt werden, um beispielsweise die dieelektrische und/oder optische Anisotropie oder andere Parameter eines solchen Dielektrikums zu optimieren. Die Verbindungen der Formel I eignen sich ferner als Zwischenprodukte zur Herstellung anderer Substanzen, die sich als Bestandteile flüssigkristalliner Phasen verwenden lassen.The compounds of formula I have a wide range Scope of application. Depending on the selection of the Substituents can be used as the base materials serve from which liquid crystalline phases are composed for the most part; it can but also compounds of formula I liquid crystalline Base materials from other classes of compounds added be, for example, the electrical and / or  optical anisotropy or other parameters of a to optimize such dielectric. The connections of the formula I are also suitable as intermediates for the production of other substances, which are constituents Allow liquid crystalline phases to be used.

Die Verbindungen der Formel I (m=0) zeigen niedrige Werte für die Viskosität und vorteilhafte Werte der elastischen Konstanten für Anwendung in hochinformativen Displays wie z. B. für STN- oder TFT-Displays.The compounds of the formula I ( m = 0) show low values for the viscosity and advantageous values for the elastic constants for use in high-information displays such as, for. B. for STN or TFT displays.

Weiter sind Verbindungen der Formel, worin m=1, hervorragend als Komponenten ferroelektrischer Flüssigkristallphasen geeignet.Furthermore, compounds of the formula in which m = 1 are outstandingly suitable as components of ferroelectric liquid crystal phases.

Die Verbindungen der Formel I sind in reinem Zustand farblos und bilden flüssigkristalline Mesophasen in einem für die elektrooptische Verwendung günstig gelegenen Temperaturbereich. Chemisch, thermisch und gegen Licht sind sie sehr stabil.The compounds of the formula I are colorless in the pure state and form liquid crystalline mesophases in one for the electro-optical use of conveniently located temperature range. They are chemical, thermal and against light very stable.

Gegenstand der Erfindung sind somit die Verbindungen der Formel I sowie die Verwendung der Verbindungen der Formel I als Komponenten flüssigkristalliner Phasen. Gegenstand der Erfindung sind ferner flüssigkristalline Phasen mit einem Gehalt an mindestens eine Verbindungen der Formel I sowie Flüssigkristallanzeigeelemente, die derartige Phasen enthalten.The invention thus relates to the compounds of Formula I and the use of the compounds of formula I. as components of liquid crystalline phases. object the invention are also liquid crystalline phases containing at least one compound of the formula I. and liquid crystal display elements that such Phases included.

Vor- und nachstehend haben R¹, Z¹, n, Z, A, A¹, m und R² die angegebene Bedeutung, sofern nicht ausdrücklich etwas anderes vermerkt ist. Above and below, R¹, Z¹, n , Z, A, A¹, m and R² have the meaning given, unless expressly stated otherwise.

Die Verbindungen der Formel I umfassen dementsprechend Verbindungen der Teilformel Ia (mit zwei Ringen), Ib bis Id (mit drei Ringen) und Ie bis If (mit vier Ringen):The compounds of formula I accordingly include Compounds of sub-formula Ia (with two rings), Ib to Id (with three rings) and Ie to If (with four rings):

R¹-Cyc-Z-A-R² (Ia)
R¹-Cyc-Cyc-Z-A-R² (Ib)
R¹-Cyc-Z¹-Cyc-Z-A-R² (Ic)
R¹-Cyc-Z-A-A¹-R² (Id)
R¹-Cyc-Cyc-Z-A-A¹-R² (Ie)
R¹-Cyc-Z¹-Cyc-Z-A-A¹-R² (If)R¹-Cyc-ZA-R² (Ia)
R¹-Cyc-Cyc-ZA-R² (Ib)
R¹-Cyc-Z¹-Cyc-ZA-R² (Ic)
R¹-Cyc-ZA-A¹-R² (Id)
R¹-Cyc-Cyc-ZA-A¹-R² (Ie)
R¹-Cyc-Z¹-Cyc-ZA-A¹-R² (If)

Darunter sind diejenigen der Teilformel Ia, Ib, Ic und Id besonders bevorzugt.These include those of sub-formula Ia, Ib, Ic and I'd be particularly preferred.

Die bevorzugten Verbindungen der Teilformel Ia umfassen solche der Teilformeln Iaa bis Iah:The preferred compounds of sub-formula Ia include those of the sub-formulas Iaa to Iah:

Darunter sind diejenigen der Formeln Iaa, Iac, Iae, Iaf und Iah besonders bevorzugt.These include those of the formulas Iaa, Iac, Iae, Iaf and Iah particularly preferred.

Die bevorzugten Verbindungen der Teilformel Ib umfassen solche der Teilformeln Iba bis Ibj:The preferred compounds of sub-formula Ib include those of the sub-formulas Iba to Ibj:

Darunter sind diejenigen der Teilformeln Ibc, Ibd, Ibe, Ibh, Ibi und Ibj bevorzugt.These include those of the sub-formulas Ibc, Ibd, Ibe, Ibh, Ibi and Ibj preferred.

Die bevorzugten Verbindungen der Teilformel Ic umfassen diejenigen der Teilformeln Ica bis Icj:The preferred compounds of sub-formula Ic include those of the sub-formulas Ica to Icj:

Darunter sind diejenigen der Formeln Icc, Icd, Icg und Ich besonders bevorzugt.These include those of the formulas Icc, Icd, Icg and I particularly preferred.

Die bevorzugten Verbindungen der Teilformel Id umfassen diejenigen der Teilformeln Ida bis Idd:The preferred compounds of sub-formula Id include those of the sub-formulas Ida to Idd:

Darunter sind diejenigen der Formeln Ida, Idc und Idd besonders bevorzugt. These include those of the formulas Ida, Idc and Idd particularly preferred.  

Die bevorzugten Verbindungen der Teilformeln Ie und If umfassen diejenigen der Teilformeln Iea bis Iec:The preferred compounds of the sub-formulas Ie and If include those of the sub-formulas Iea to Iec:

Darin bedeutet Z¹ vorzugsweise eine Einfachbindung.Z 1 is preferably a single bond.

In den Verbindungen der vor- und nachstehenden Formeln bedeuten R¹ und R² vorzugsweise Alkyl, -O-Alkyl, -OCO- Alkyl oder Oxaalkyl.In the compounds of the formulas above and below R¹ and R² are preferably alkyl, -O-alkyl, -OCO- Alkyl or oxaalkyl.

Besonders bevorzugt bedeutet R¹ Alkyl und R² Alkyl, Alkoxy oder -OCO-Alkyl.R 1 is particularly preferably alkyl and R 2 is alkyl, alkoxy or -OCO-alkyl.

Ferner sind für R¹ und/oder R² Alkenylgruppen bevorzugt.
Z-A bedeutet in erster Linie bevorzugtFurthermore, alkenyl groups are preferred for R 1 and / or R 2.
ZA primarily means preferred

in zweiter Linie bevorzugtpreferred in the second place

Z¹ bedeutet -CH₂CH- oder eine Einfachbindung, vorzugsweise eine Einfachbindung. Z¹ means -CH₂CH- or a single bond, preferably a single bond.  

FallsIf

ist R² = O-CO-Alkyl und/oder
m = 1 und/oder Z¹ = -CH₂CH₂.
Cyc bedeutet eine trans-1,4-Cyclohexylengruppe und A¹ = -O-CO-Phe.
Phe ist vorzugsweise eine unsubstituierte 1,4-Phenylengruppe, kann aber auch ein- oder mehrfach, vorzugsweise ein- oder zweifach durch F, Cl, CH₃ und/oder CN substituiert vorliegen. Bevorzugt ist eine Mono-Substitution durch Fluor, insbesondere bevorzugt ist eine Di-Substitution in 2,3-Position durch Fluor.
n bedeutet vorzugsweise 1 und m vorzugsweise 0.R² = O-CO-alkyl and / or
m = 1 and / or Z¹ = -CH₂CH₂.
Cyc means a trans-1,4-cyclohexylene group and A¹ = -O-CO-Phe.
Phe is preferably an unsubstituted 1,4-phenylene group, but can also be substituted one or more times, preferably once or twice, by F, Cl, CH₃ and / or CN. Mono substitution by fluorine is preferred, and di-substitution in the 2,3-position by fluorine is particularly preferred.
n is preferably 1 and m is preferably 0.

Die Alkylreste in den Gruppen R¹ und/oder R² können geradkettig oder verzweigt sein. Vorzugsweise sind sie geradkettig, haben 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 oder 12 C-Atome und bedeuten demnach bevorzugt Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Octyl, Nonyl, Decyl, Undecyl oder Dodecyl, ferner Tridecyl, Tetradecyl oder Pentadecyl.The alkyl radicals in the groups R¹ and / or R² can straight chain or branched. They are preferably straight chain, have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and are therefore preferably methyl, Ethyl, propyl, butyl, pentyl, hexyl, octyl, Nonyl, decyl, undecyl or dodecyl, furthermore tridecyl, Tetradecyl or pentadecyl.

Insbesondere bevorzugt sind Verbindungen der Formel I
mit R² = Methyl, m = 0 undCompounds of the formula I are particularly preferred
with R² = methyl, m = 0 and

Falls R¹ und/oder R² Alkylreste bedeuten, in denen eine ("Alkoxy" bzw. "Oxaalkyl") oder zwei ("Alkoxyalkoxy" bzw. "Dioxaalkyl") CH₂-Gruppen durch O-Atome ersetzt sind, so können sie geradkettig, oder verzweigt sein. Vorzugsweise sind sie geradkettig, haben 2, 3, 4, 5, 6 oder 7 C-Atome und bedeuten demnach bervorzugt Ethoxy, Propoxy, Butoxy, Pentoxy, Hexoxy, Heptoxy, 2-Oxapropyl (=Methoxymethyl), 2- (=Ethoxymethyl) oder 3-Oxabutyl (=2-Methoxyethyl), 2-, 3- oder 4-Oxypentyl, 2-, 3-, 4- oder 5-Oxahexyl, 2-, 3-, 4-, 5- oder 6-Oxaheptyl, ferner Methoxy, Octoxy, Nonoxy, Decoxy, 2-, 3-, 4-, 5-, 6- oder 7-Oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- oder 8-Oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- oder 9-Oxadecyl, 1,3-Dioxabutyl (=Methoxymethyl), 1,3-, 1,4- oder 2,4-Dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,4- oder 3,5-Dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- oder 4,6-Dioxaheptyl.If R¹ and / or R² are alkyl radicals in which one ("Alkoxy" or "oxaalkyl") or two ("alkoxyalkoxy" or "Dioxaalkyl") CH₂ groups replaced by O atoms are straight-chain or branched. They are preferably straight-chain, have 2, 3, 4, 5, 6 or 7 carbon atoms and therefore preferably mean ethoxy, Propoxy, butoxy, pentoxy, hexoxy, heptoxy, 2-oxapropyl (= Methoxymethyl), 2- (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxypentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, further Methoxy, octoxy, nonoxy, decoxy, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl, 1,3-dioxabutyl (= Methoxymethyl), 1,3-, 1,4- or 2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,4- or 3,5-dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- or 4,6-dioxaheptyl.

Verbindungen der Formel I sind vor- und nachstehenden Teilformeln mit verzweigten Flügelgruppen R¹ bzw. R² können gelegentlich wegen einer besseren Löslichkeit in den üblichen flüssigkristallinen Basismaterialien von Bedeutung sein. Verzweigte Gruppen dieser Art enthalten in der Regel nicht mehr als eine Kettenverzweigung. Bevorzugte verzweigte Reste R² und R¹ sind Isopropyl, 2-Butyl (=1-Methoxypropyl), Isobutyl (=2-Methylpropyl), 2-Methylbutyl, Isopentyl (=3-Methylbutyl), 2-Methylpentyl, 3-Methylpentyl, 2-Ethylhexyl, 2-Propylpentyl, 2-Octyl, Isopropoxy, 2-Methylpropoxy, 2-Methylbutoxy, 3-Methylbutoxy, 2-Methylpentoxy, 3-Methylpentoxy, 2- Ethylhexoxy, 1-Methylhexoxy, 1-Methylheptoxa, 2-Oxa- 3-methylbutyl, 3-Oxa-4-methylpentyl, 2-Octyloxy, 2-Methyl- 3-oxapentyl, 2-Methyl-3-oxa-hexyl. Compounds of formula I are above and below Partial formulas with branched wing groups R¹ or R² can occasionally be due to better solubility in the usual liquid crystalline base materials from Be meaningful. Branched groups of this type contain usually no more than one chain branch. Preferred branched radicals R² and R¹ are isopropyl, 2-butyl (= 1-methoxypropyl), isobutyl (= 2-methylpropyl), 2-methylbutyl, isopentyl (= 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2- Ethylhexoxy, 1-methylhexoxy, 1-methylheptoxa, 2-oxa- 3-methylbutyl, 3-oxa-4-methylpentyl, 2-octyloxy, 2-methyl 3-oxapentyl, 2-methyl-3-oxa-hexyl.  

Falls R¹ und/oder R² einen Alkenylrest bedeuten, so kann dieser geradkettig oder verzweigt sein. Vorzugsweise ist er geradkettig und hat 2 bis 10 C-Atome. Er bedeutet demnach bevorzugt Vinyl, Prop-1- oder Prop-2-enyl, But-1-, 2- oder But-3-enyl, Pent-1-, 2-, 3- oder Pent-4-enyl, Hex-1-, 2-, 3-, 4- oder Hex-5-enyl, Hept-1-, 2-, 3-, 4-, 5- oder Hept-6-enyl, Oct-1-, 2-, 3-, 4-, 5-, 6- oder Oct-7-enyl, Non-1-, 2-, 3-, 4-, 5-, 6-, 7- oder Non-8- enyl, Dec-1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- oder Dec-9-enyl.If R¹ and / or R² represent an alkenyl radical, then this can be straight-chain or branched. Preferably it is straight-chain and has 2 to 10 carbon atoms. So it means preferably vinyl, prop-1 or prop-2-enyl, but-1-, 2- or but-3-enyl, pent-1-, 2-, 3- or pent-4-enyl, Hex-1-, 2-, 3-, 4- or hex-5-enyl, hept-1-, 2-, 3-, 4-, 5- or hept-6-enyl, oct-1-, 2-, 3-, 4-, 5-, 6- or Oct-7-enyl, non-1-, 2-, 3-, 4-, 5-, 6-, 7- or non-8- enyl, Dec-1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or Dec-9-enyl.

Die Verbindungen der Formel I werden nach an sich bekannten Methoden hergestellt, wie sie in der Literatur (z. B. in den Standardwerken wie Houben Weyl, Methoden der Organischen Chemie, Georg-Thieme-Verlag, Stuttgart) beschrieben sind, und zwar unter Reaktionsbedingungen, die für die genannten Umsetzungen bekannt und geeignet sind. Dabei kann man von an sich bekannten, hier nicht erwähnten Varianten Gebrauch machen.The compounds of formula I are known per se Methods produced as described in the literature (e.g. in the standard works such as Houben Weyl, methods of organic chemistry, Georg-Thieme-Verlag, Stuttgart) are described, namely under reaction conditions, known and suitable for the above-mentioned implementations are. One can of known here, not here make use of the variants mentioned.

Ester der Formel I können durch Veresterung entsprechender Carbonsäuren (oder ihren reaktionsfähigen Derivaten) mit entsprechenden 2-substituierten Pyridin-5-olen (oder den reaktionsfähigen Derivaten) erhalten werden.Esters of the formula I can be correspondingly esterified Carboxylic acids (or their reactive derivatives) with corresponding 2-substituted pyridin-5-ols (or the reactive derivatives) can be obtained.

Als reaktionsfähige Derivate der genannten Carbonsäuren eignen sich insbesondere die Säurehalogenide, vor allem die Chloride und Bromide, ferner die Anhydride, Azide und Ester, insbesondere Alkylester mit 1-4 C-Atomen in der Alkylgruppe.As reactive derivatives of the carboxylic acids mentioned the acid halides are particularly suitable the chlorides and bromides, also the anhydrides, azides and esters, in particular alkyl esters with 1-4 C atoms in the alkyl group.

Als reaktionsfähige Derivate der genannten Pyridin-5-olen kommen insbesondere die entsprechenden Metallalkoholate, vorzugsweise eines Alkalimetalls wie Na oder K, in Betracht. As reactive derivatives of the pyridin-5-ols mentioned come especially the corresponding metal alcoholates, preferably an alkali metal such as Na or K, into consideration.  

Die Umsetzungen werden vorzugsweise in Toluol/Pyridin, ausgehend vom Säurechlorid, oder auch mit DCC (Dicyclohexylcarbodiimid) in Gegenwart katalytischer Mengen DMAP (Dimethylaminopyridin) durchgeführt, ausgehend von der Carbonsäure selbst.The reactions are preferably carried out in toluene / pyridine, starting from acid chloride, or with DCC (dicyclohexylcarbodiimide) in the presence of catalytic amounts of DMAP (Dimethylaminopyridine) carried out starting from the Carboxylic acid itself.

Ether der Formel I (worin Z=-CH₂O-) sind durch Veretherung entsprechender Hydroxyverbindungen herstellbar, wobei die Hydroxyverbindungen zweckmäßig zunächst in ein entsprechendes Metallderivat, z. B. durch Behandeln mit NaH, NaNH₂, NaOH, KOH, Na₂CO₃ oder K₂CO₃, überführt wird. Dieses Metallderivat kann dann mit dem entsprechenden Alkylhalogenid, -sulfonat oder Dialkylsulfonat umgesetzt werden, zweckmäßig in einem inerten Lösungsmittel wie Aceton, 1,2- Dimethoxyethan, DMF oder Dimethylsulfoxid oder auch einem Überschuß an wäßriger oder wäßrig-alkoholischer NaOH oder KOH bei Temperaturen zwischen etwa 20°C und 100°C.Ethers of formula I (wherein Z = -CH₂O-) are etherified corresponding hydroxy compounds can be produced, wherein the hydroxy compounds are appropriate first in a corresponding Metal derivative, e.g. B. by treatment with NaH, NaNH₂, NaOH, KOH, Na₂CO₃ or K₂CO₃, is transferred. This metal derivative can then with the corresponding alkyl halide, sulfonate or dialkyl sulfonate are reacted, expediently in an inert solvent such as acetone, 1,2- Dimethoxyethane, DMF or dimethyl sulfoxide or one Excess of aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 20 ° C and 100 ° C.

Verbindungen der Formel I mitCompounds of formula I with

sind beispielsweise erhältlich durch Umsetzung der entsprechenden 2-Methylpyridine mit dem entsprechenden Alkylierungsmittel in Gegenwart einer Base wie z. B. Lithiumdiisopropylamid.are available, for example, by implementing the corresponding 2-methylpyridines with the corresponding alkylating agent in the presence of a base such as e.g. B. Lithium diisopropylamide.

Die Ethanderivate können auch hergestellt werden durch Hydrierung der entsprechenden Alkene. Die Hydrierungen können nach allgemein bekannten Methoden durchgeführt werden.The ethane derivatives can also be prepared by hydrogenation of the corresponding alkenes. The hydrogenations can be carried out according to generally known methods.

Die Ausgangsverbindungen sind entweder bekannt oder durch einfache, literaturbekannte Reaktionen herstellbar. The starting compounds are either known or by simple reactions known from the literature can be produced.  

Die erfindungsgemäßen flüssigkristallinen Phasen bestehen aus 2 bis 25, vorzugsweise 3 bis 15 Komponenten, darunter mindestens einer Verbindung der Formel I. Die anderen Bestandteile werden vorzugsweise ausgewählt aus den nematischen oder nematogenen Substanzen, insbesondere den bekannten Substanzen, aus den Klassen der Azoxybenzole, Benzylidenaniline, Biphenyle, Terphenyle, Phenyl- oder Cyclohexylbenzoate, Cyclohexancarbonsäurephenyl- oder -cyclohexyl-ester, Phenylcyclohexane, Cyclohexylbiphenyle, Cyclohexylcyclohexane, Cyclohexylnaphtaline, 1,4-Bis- cyclohexylbenzole, 4,4′-Bis-cyclohexylbiphenyle, Phenyl- oder Cyclohexylpyrimidine, Phenyl- oder Cyclohexyldioxane, Phenyl- oder Cyclohexyl-1,3-dithiane, 1,2-Bis-cyclohexylethane, 1,2-Bis-phenylethane, 1-Phenyl-2-cyclohexylethane, gegebenenfalls halogenierten Stilbene, Benzylphenylether, Tolane und substituierten Zimtsäuren.The liquid-crystalline phases according to the invention consist from 2 to 25, preferably 3 to 15 components, including at least one compound of formula I. The other ingredients are preferably selected from the nematic or nematogenic substances, especially the known substances from the classes of azoxybenzenes, Benzylidenanilines, biphenyls, terphenyls, phenyl or Cyclohexylbenzoate, cyclohexane carboxylic acid phenyl or -cyclohexyl esters, phenylcyclohexanes, cyclohexylbiphenyls, Cyclohexylcyclohexane, Cyclohexylnaphtaline, 1,4-Bis- cyclohexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, phenyl or cyclohexylpyrimidines, phenyl- or cyclohexyldioxanes, Phenyl- or cyclohexyl-1,3-dithiane, 1,2-bis-cyclohexylethane, 1,2-bis-phenylethane, 1-phenyl-2-cyclohexylethane, optionally halogenated stilbenes, benzylphenyl ether, Tolanes and substituted cinnamic acids.

Die wichtigsten als Bestandteile derartiger flüssigkristalliner Phasen in Frage kommenden Verbindungen lassen sich durch die Formel II charakterisieren,The most important as components of such liquid crystalline Phases in question connections can be characterized by Formula II,

R′-L-G-E-R′′ (II)R′-L-G-E-R ′ ′ (II)

worin L und E je ein carbo- oder heterocyclisches Ringsystem aus der aus 1,4-disubstituierten Benzol- und Cyclohexanringen, 4,4′-disubstituierten Biphenyl-, Phenylcyclohexan- und Cyclohexylcyclohexansystemen, 2,5-disubstituierten Pyrimidin- und 1,3-Dioxanringen, 2,6-disubstituiertem Naphthalin, Di- und Tetrahydronaphthalin, Chinazolin und Tetrahydrochinazolin gebildeten Gruppe, where L and E each have a carbocyclic or heterocyclic ring system from 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted Pyrimidine and 1,3-dioxane rings, 2,6-disubstituted Naphthalene, di- and tetrahydronaphthalene, quinazoline and Group formed tetrahydroquinazoline,  

oder eine C-C-Einfachbindung, Y Halogen, vorzugsweise Chlor, oder -CN, und R′ und R′′ Alkyl, Alkoxy, Alkanoyloxy oder Alkoxycarbonyloxy mit bis zu 18, vorzugsweise bis zu 8 Kohlenstoffatomen, oder einer dieser Reste aus CN, NC, NO₂, CF₃, F, Cl oder Br bedeuten.or a C-C single bond, Y halogen, preferably Chlorine, or -CN, and R 'and R' 'alkyl, alkoxy, alkanoyloxy or alkoxycarbonyloxy with up to 18, preferably up to to 8 carbon atoms, or one of these residues from CN, NC, NO₂, CF₃, F, Cl or Br mean.

Bei den meisten dieser Verbindungen sind R′ und R′′ voneinander verschieden, wobei einer dieser Reste meist eine Alkyl- oder Alkoxygruppe ist. Aber auch andere Varianten der vorgesehenen Substituenten sind gebräuchlich. Viele solcher Substanzen oder auch Gemische davon sind im Handel erhältlich. Alle dieser Substanzen sind nach literaturbekannten Methoden herstellbar.Most of these compounds are R ′ and R ′ ′ different from one another, one of these residues usually one Is alkyl or alkoxy group. But also other variants the proposed substituents are common. Lots such substances or mixtures thereof are commercially available available. All of these substances are known from the literature Methods can be produced.

Die erfindungsgemäßen Phasen enthalten etwa 0,1 bis 99, vorzugsweise 10 bis 95%, einer oder mehrerer Verbindungen der Formel I. Weiterhin bevorzugt sind erfindungsgemäße Dielektrika enthaltend 0,1 bis 40, vorzugsweise 0,5 bis 30%, einer oder mehrerer Verbindungen der Formel I.The phases according to the invention contain about 0.1 to 99, preferably 10 to 95%, one or more compounds of formula I. Furthermore preferred according to the invention Dielectrics containing 0.1 to 40, preferably 0.5 to 30%, one or more compounds of formula I.

Verbindungen der Formel I, worin m=1 ist, sind hervorragend als Komponenten ferroelektrischer Flüssigkristallphasen beispielsweise für Displays nach dem SSFLC-Prinzip.Compounds of the formula I in which m = 1 are outstanding as components of ferroelectric liquid crystal phases, for example for displays based on the SSFLC principle.

Die Herstellung der erfindungsgemäßen Dielektrika erfolgt in an sich üblicher Weise. In der Regel werden die Komponenten ineinander gelöst, zweckmäßig bei erhöhter Temperatur. The dielectrics according to the invention are produced in the usual way. As a rule, the components dissolved in one another, expediently at elevated temperature.  

Durch geeignete Zusätze können die flüssigkristallinen Dielektrika nach der Erfindung so modifiziert werden, daß sie in allen bisher bekannt gewordenen Arten von Flüssigkristallanzeigeelementen verwendet werden können.By means of suitable additives, the liquid crystalline Dielectrics are modified according to the invention that they are known in all types of Liquid crystal display elements can be used.

Derartige Zusätze sind dem Fachmann bekannt und in der Literatur ausführlich beschrieben. Beispielsweise können Leitsalze, vorzugsweise Ethyl-dimethyl-dodecyl-ammonium- 4-hexyloxybenzoat, Tetrabutylammonium-tetraphenylboranat oder Komplexsalze von Kronenethern (vgl. z. B. I. Haller et al., Mol. Cryst. Liq. Cryst. Band 24, Seiten 249-258 (1973)) zur Verbesserung der Leitfähigkeit, dichroitische Farbstoffe zur Herstellung farbiger Guest-Host-Systeme oder Substanzen zur Veränderung der dielektrischen Anisotropie, der Viskosität und/oder der Orientierung der nematischen Phasen zugesetzt werden. Derartige Substanzen sind z. B. in den DE-OS 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 und 29 02 177 beschrieben.Such additives are known to the expert and in the Literature described in detail. For example, you can Conductive salts, preferably ethyl-dimethyl-dodecyl-ammonium 4-hexyloxybenzoate, tetrabutylammonium tetraphenylboranate or complex salts of crown ethers (cf. e.g. I. Haller et al., Mol. Cryst. Liq. Cryst. Volume 24, pages 249-258 (1973)) to improve conductivity, dichroic Dyes for the production of colored guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases are added. Such substances are z. B. in DE-OS 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 and 29 02 177 described.

Die folgenden Beispiele sollen die Erfindung erläutern, ohne sie zu begrenzen. Fp.=Schmelzpunkt, Kp.=Klärpunkt. Vor- und nachstehend bedeuten Prozentangaben Gewichtsprozent; alle Temperaturangaben sind in Grad Celsius angegeben. "Übliche Aufarbeitung" bedeutet: man gibt Wasser hinzu, extrahiert mit Methylenchlorid, trennt ab, trocknet die organische Phase, dampft ein und reinigt das Produkt durch Kristallisation, Destillation und/oder Chromatographie.The following examples are intended to illustrate the invention, without limiting it. Mp. = Melting point, Kp. = Clearing point. Percentages above and below mean percentages by weight; all temperatures are in degrees Celsius specified. "Usual work-up" means: one gives Add water, extract with methylene chloride, separate, dries the organic phase, evaporates and cleans the product by crystallization, distillation and / or Chromatography.

C, S, N und I bedeuten kristalliner, smektischer, nematischer und isotroper Zustand. Die Zahlen dazwischen stellen die Übergangstemperaturen dar.C, S, N and I mean crystalline, smectic, nematic and isotropic state. Put the numbers in between represent the transition temperatures.

Beispiel 1Example 1

Zu einer Suspension von 22,4 g trans-4-(trans-4-Pentyl­ cyclohexyl)cyclohexancarbonsäure, 13,3 g 2-Pentyl-5-hydroxy­ pyridin (Herstellung: Bei -50°C gibt man zu einer Lösung von 53 g Diisopropylamin in 350 ml THF 320 ml einer 1,6 m Lösung von n-Butyllithium in Hexan, 27,3 g 2-Methyl-5-hydroxypyridin in 750 ml THF und 44,5 g 1-Brombutan. Man rührt noch 30 Min. und läßt das Reaktionsgemisch dann auf Raumtemperatur kommen, hydrolysiert und stellt mit HCl einen pH-Wert von etwa 6,5 ein. Die organische Phase wird abgetrennt und aufgearbeitet. Nach chromatographischer Reinigung (Hexan/ Kieselgel) erhält man 2-Pentyl-5-hydroxypyridin.) und einer katalytischen Menge Dimethylaminopyridin (DMAP) in 200 ml CH₂Cl₂ gibt man bei 0°-5° eine Lösung von 18,2 g DCC in 50 ml CH₂CL₂. Anschließend rührt man 12 Stunden bei Raumtemperatur, filtriert den ausgefallenen Dicyclohexylharnstoff ab und arbeitet das Filtrat wie üblich auf. Nach Reinigung durch Chromatographie oder Kristallisation erhält man trans-4-(trans-4-Pentylcyclohexyl)-cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)-ester mit K 31° SB 181° N 183,1° I.To a suspension of 22.4 g of trans-4- (trans-4-pentyl cyclohexyl) cyclohexane carboxylic acid, 13.3 g of 2-pentyl-5-hydroxy pyridine (preparation: at -50 ° C., a solution of 53 g is added Diisopropylamine in 350 ml THF 320 ml of a 1.6 m solution of n-butyllithium in hexane, 27.3 g 2-methyl-5-hydroxypyridine in 750 ml THF and 44.5 g 1-bromobutane. The reaction mixture is then brought to room temperature, hydrolyzed and adjusted to a pH of about 6.5 with HCl. The organic phase is separated off and worked up. After chromatographic purification (hexane / silica gel), 2-pentyl-5-hydroxypyridine is obtained .) and a catalytic amount of dimethylaminopyridine (DMAP) in 200 ml of CH₂Cl₂ are given at 0 ° -5 ° a solution of 18.2 g DCC in 50 ml of CH₂CL₂. The mixture is then stirred for 12 hours at room temperature, the precipitated dicyclohexylurea is filtered off and the filtrate is worked up as usual. After purification by chromatography or crystallization, trans-4- (trans-4-pentylcyclohexyl) cyclohexanecarboxylic acid (2-pentyl-pyridin-5-yl) ester with K 31 ° S B 181 ° N 183.1 ° I is obtained.

Analog werden hergestellt:The following are produced analogously:

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)ester, K 4° SB 170° N 180.8° I
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)ester, K 20° SB 178° N 179,3° I
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-pentyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester, K 4 ° S B 170 ° N 180.8 ° I
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester, K 20 ° S B 178 ° N 179.3 ° I
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-methyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexanecarboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Proppylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-ethyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-propyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-butyl-pyridin-2-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-butyl-pyridin-2-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-hexyl-pyridin-2-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-hexyl-pyridin-2-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-heptyl-pyridin-2-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-heptyl-pyridin-2-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-methyl-pyridin-5-yl)ester trans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-propyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-butyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-heptyl-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-pentyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-pentyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-ester, Fp. 40°, Kp. 0°
trans-4-Butylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-ester, Fp. 41°, Kp. 20°
trans-4-Pentylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-ester, Fp. 48°, Kp. 39°
trans-4-Hexylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-methyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester, mp. 40 °, bp. 0 °
trans-4-butylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester, mp. 41 °, bp. 20 °
trans-4-pentylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester, mp. 48 °, bp. 39 °
trans-4-hexylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-methyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-ethyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-ethyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-propyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-propyl-pyridin-5-yl) ester
trans-4-heptylcyclohexanecarboxylic acid (2-propyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-butyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-butyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-hexyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-hexyl-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-heptyl-pyridin- 5-yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-heptyl-pyridin-5-yl) ester

Beispiel 2Example 2

Zu 0,1 mol trans-4-Pentylcyclohexancarbonsäure, 0,1 mol 5-Hydroxy-2-methoxy-pyridin (Darstellung analog R. Adams et al., J. Amer. Chem. Soc. 69, 1806-1808 (1947) und L. Rodes et al., Rev. CENIC, Cienc Fis (1973), 4 (1-2), 81-7, CA 84 745050x) und einer katalytischen Menge DMAP in 250 ml CH₂Cl₂ gibt man unter Feuchtigkeitsausschluß bei 0° eine Lösung von 0,1 mol DCC in CH₂Cl₂. Man rührt 12 Stunden bei Raumtemperatur, filtriert den Dicyclohexylharnstoff ab und arbeitet das Filtrat auf. To 0.1 mol of trans-4-pentylcyclohexane carboxylic acid, 0.1 mol 5-Hydroxy-2-methoxy-pyridine (analogous to R. Adams et al., J. Amer. Chem. Soc. 69, 1806-1808 (1947) and L. Rodes et al., Rev. CENIC, Cienc Fis (1973), 4 (1-2), 81-7, CA 84 745050x) and a catalytic amount of DMAP in 250 ml of CH₂Cl₂ there is with exclusion of moisture at 0 ° a solution of 0.1 mol DCC in CH₂Cl₂. You stir 12 hours at room temperature, filter the dicyclohexylurea and works up the filtrate.  

Nach Reinigung durch Chromatographie und/oder Kristallisation erhält man trans-4-Pentylcyclohexancarbonsäure-(2- methoxy-pyridin-5-yl)-ester.After purification by chromatography and / or crystallization is obtained trans-4-pentylcyclohexane carboxylic acid (2- methoxy-pyridin-5-yl) ester.

Analog werden hergestellt:The following are produced analogously:

trans-4-Ethylcyclohexancarbonsäure-(2-methoxypyridin-5- yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-methoxypyridin-5- yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-methoxypyridin-5- yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-ethoxy-pyridin-5- yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-ethoxy-pyridin-5- yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-ethoxy-pyridin-5- yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-ethoxy-pyridin-5- yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-ethoxy-pyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-ethoxy-pyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-ethoxy-pyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-ethoxy-pyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-propoxypyridin-5- yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-propoxypyridin-5- yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-propoxypyridin-5- yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-propoxypyridin-5- yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-butoxypyridin-5- yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester

trans-4-Ethylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-ester
trans-4-Propylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-ester
trans-4-Butylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-ester
trans-4-Pentylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-ester
trans-4-Hexylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-ester
trans-4-Heptylcyclohexancarbonsäure-(2-pentyloxypyridin-5- yl)-estertrans-4-ethylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4-propylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4-butylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4-pentylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4-hexylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4-heptylcyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-pentyloxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylycyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-methoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-butylycyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-ethoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-ethoxy-pyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-propoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-butoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexylethyl)cyclohexancarbon­ säure-(2-hexyloxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexylethyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-pentyloxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-pentyloxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-methoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-methoxy-pyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-methoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-ethoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexanecarboxylic acid (2-ethoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-ethoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-propoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexanecarboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-propoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-butoxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexanecarboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexanecarboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-butoxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexanecarboxylic acid (2-butoxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-hexyloxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-hexyloxypyridin-5-yl) ester

trans-4-(trans-4-Ethylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Pentylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Hexylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)ester
trans-4-(trans-4-Heptylcyclohexyl)cyclohexancarbonsäure- (2-heptyloxy-pyridin-5-yl)estertrans-4- (trans-4-ethylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester
trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester
trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester
trans-4- (trans-4-pentylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester
trans-4- (trans-4-hexylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester
trans-4- (trans-4-heptylcyclohexyl) cyclohexane carboxylic acid (2-heptyloxypyridin-5-yl) ester

Beispiel 3Example 3

  • a) 0,1 mol trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyliodid, 13,8 g wasserfreies K₂CO₃, 0,1 mol 3- Hydroxy-6-methylpyridin und 1,1 g Benzyltriethyl­ ammoniumchlorid werden in 100 ml Methylethylketon 30 Stunden am Rückfluß erhitzt. Das Reaktionsgemisch wird mit Wasser versetzt und die organische Phase wie üblich aufgearbeitet. Nach Reinigung durch Kristallisation erhält man trans-4-(trans-4-Ethylcyclohexycyclohexyllmethyl- (2-methyl-pyridin-5-yl)ether.a) 0.1 mol of trans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl iodide, 13.8 g anhydrous K₂CO₃, 0.1 mol 3- Hydroxy-6-methylpyridine and 1.1 g benzyltriethyl ammonium chloride in 100 ml of methyl ethyl ketone Heated at reflux for 30 hours. The reaction mixture is mixed with water and the organic phase as worked up as usual. After cleaning by crystallization you get  trans-4- (trans-4-ethylcyclohexycyclohexyllmethyl- (2-methyl-pyridin-5-yl) ether.
  • b) Man gibt bei -30°C zu einer Lösung von Lithiumdi­ isopropylamid (1,44 g Diisopropylamin und 3 ml 1,6 N Butyllithium in Hexan) in 25 ml THF 1,83 g 1,3-Di­ methyltetrahydro-2-(1H)-pyrimidinon (DMPU), 5,2 g des in a) hergestellten Pyridinethers und 1,81 g Brombutan. Anschließend rührt man das Reaktionsgemisch 12 Stunden unter langsamer Erwärmung auf Raumtemperatur. Nach üblicher Aufarbeitung erhält man trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl- (2-pentyl-pyridin-5-yl)-ether.b) It is added to a solution of lithium di at -30 ° C. isopropylamide (1.44 g diisopropylamine and 3 ml 1.6 N Butyllithium in hexane) in 25 ml THF 1.83 g 1,3-di methyltetrahydro-2- (1H) pyrimidinone (DMPU), 5.2 g of the pyridine ether prepared in a) and 1.81 g Bromobutane. The reaction mixture is then stirred 12 hours with slow warming up Room temperature. After usual work-up to make trans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether.

Analog werden hergestellt:The following are produced analogously:

trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimid-in- 5-yl)ether, Fp. 92°, Kp. 148°
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimidi-n- 5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimid-in- 5-yl)ether
trans-4-(trans-4-Hexylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimidi-n- 5-yl)ether
trans-4-(trans-4-Heptylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimid-in- 5-yl)ether
trans-4-(trans-4-Octylcyclohexyl)cyclohexylmethyl-(2-methyl-pyrimidi-n- 5-yl)ethertrans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl- (2-methyl-pyrimid-in-5-yl) ether, mp 92 °, bp 148 °
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-methyl-pyrimidi-n-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-methyl-pyrimid-in-5-yl) ether
trans-4- (trans-4-hexylcyclohexyl) cyclohexylmethyl- (2-methyl-pyrimidi-n-5-yl) ether
trans-4- (trans-4-heptylcyclohexyl) cyclohexylmethyl (2-methyl-pyrimid-in-5-yl) ether
trans-4- (trans-4-octylcyclohexyl) cyclohexylmethyl- (2-methyl-pyrimidi-n-5-yl) ether

trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ether
trans-4-(trans-4-Hexylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ether
trans-4-(trans-4-Heptylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ether
trans-4-(trans-4-Octylcyclohexyl)cyclohexylmethyl-(2- pentyl-pyridin-5-yl)ethertrans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether
trans-4- (trans-4-hexylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether
trans-4- (trans-4-heptylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether
trans-4- (trans-4-octylcyclohexyl) cyclohexylmethyl (2-pentyl-pyridin-5-yl) ether

trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl-(2- ethyl-pyridin-5-yl)ether
trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- ethyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- ethyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- ethyl-pyridin-5-yl)ethertrans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-ethyl-pyridin-5-yl) ether

trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl-(2- propyl-pyridin-5-yl)ether
trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- propyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- propyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- propyl-pyridin-5-yl)ethertrans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-propyl-pyridin-5-yl) ether
trans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-propyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-propyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-propyl-pyridin-5-yl) ether

trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl-(2- butyl-pyridin-5-yl)ether
trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- butyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- butyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- butyl-pyridin-5-yl)ethertrans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-butyl-pyridin-5-yl) ether
trans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-butyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-butyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-butyl-pyridin-5-yl) ether

trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl-(2- hexyl-pyridin-5-yl)ether
trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- hexyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- hexyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- hexyl-pyridin-5-yl)ethertrans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-hexyl-pyridin-5-yl) ether
trans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-hexyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-hexyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-hexyl-pyridin-5-yl) ether

trans-4-(trans-4-Ethylcyclohexyl)cyclohexylmethyl-(2- heptyl-pyridin-5-yl)ether
trans-4-(trans-4-Propylcyclohexyl)cyclohexylmethyl-(2- heptyl-pyridin-5-yl)ether
trans-4-(trans-4-Butylcyclohexyl)cyclohexylmethyl-(2- heptyl-pyridin-5-yl)ether
trans-4-(trans-4-Pentylcyclohexyl)cyclohexylmethyl-(2- heptyl-pyridin-5-yl)ethertrans-4- (trans-4-ethylcyclohexyl) cyclohexylmethyl (2-heptyl-pyridin-5-yl) ether
trans-4- (trans-4-propylcyclohexyl) cyclohexylmethyl (2-heptyl-pyridin-5-yl) ether
trans-4- (trans-4-butylcyclohexyl) cyclohexylmethyl (2-heptyl-pyridin-5-yl) ether
trans-4- (trans-4-pentylcyclohexyl) cyclohexylmethyl (2-heptyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-methylpyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-methylpyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-methylpyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-methylpyridin-5-yl)- ether
trans-4-Octylcyclohexylmethyl-(2-methylpyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-methylpyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-methylpyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-methylpyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-methylpyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl (2-methylpyridin-5-yl) ether
trans-4-octylcyclohexylmethyl- (2-methylpyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl- (2-methylpyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-pentyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl- (2-pentyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-ethyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-ethyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl (2-ethyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl (2-ethyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-propyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-propyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-propyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl (2-propyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl (2-propyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-propyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl (2-propyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-butyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl- (2-butyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-hexyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl- (2-hexyl-pyridin-5-yl) ether

trans-4-Ethylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ether
trans-4-Propylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ether
trans-4-Butylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ether
trans-4-Pentylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ether
trans-4-Hexylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ether
trans-4-Heptylcyclohexylmethyl-(2-heptyl-pyridin-5-yl)- ethertrans-4-ethylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether
trans-4-propylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether
trans-4-butylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether
trans-4-pentylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether
trans-4-hexylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether
trans-4-heptylcyclohexylmethyl- (2-heptyl-pyridin-5-yl) ether

Beispiel 4Example 4

0,1 m 5-Hydroxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl) cyclohexyl]ethyl}-pyridin (Darstellung erfolgt z. B. durch Umsetzung von 2-Methyl-5-hydroxypyridin und trans- 4-(trans-4-Pentylcyclohexylethyl)-cyclohexylmethyliodid analog Beispiel 1) werden in Methylethylketon in Gegenwart von 0,12 mol K₂CO₃ (wasserfrei) und 0,1 mol Brompentan 24 Stunden am Rückfluß erhitzt. Man arbeitet wie üblich auf und erhält nach chromatographischer Reinigung 5-Pentyloxy- 2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)cyclohexyl] ethyl}-pyridin.0.1 m 5-hydroxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine (shown for example by reacting 2-methyl-5-hydroxypyridine and trans 4- (trans-4-pentylcyclohexylethyl) cyclohexylmethyl iodide analogously to Example 1) in methyl ethyl ketone in the presence of 0.12 mol K₂CO₃ (anhydrous) and 0.1 mol bromopentane Heated at reflux for 24 hours. You work up as usual and, after chromatographic purification, receives 5-pentyloxy 2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine.

Analog werden hergestellt:The following are produced analogously:

5-Pentyloxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Pentyloxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Pentyloxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Butoxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Butoxy2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Butoxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Butoxy2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-pentyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-pentyloxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-pentyloxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-butoxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-butoxy2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-butoxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-butoxy2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

5-Propoxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Propoxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Propoxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Propoxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-propoxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-propoxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-propoxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-propoxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

5-Ethoxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Ethoxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Ethoxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Ethoxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-ethoxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-ethoxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-ethoxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-ethoxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

5-Methoxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Methoxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Methoxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Methoxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-methoxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-methoxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-methoxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-methoxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

5-Hexyloxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Hexyloxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Hexyloxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Hexyloxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-Hexyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-Hexyloxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-Hexyloxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-Hexyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

5-Heptyloxy-2-{2-[trans-4-(trans-4-ethylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Heptyloxy-2-{2-[trans-4-(trans-4-propylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Heptyloxy-2-{2-[trans-4-(trans-4-butylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin
5-Heptyloxy-2-{2-[trans-4-(trans-4-pentylcyclohexylethyl)- cyclohexyl]ethyl}-pyridin5-heptyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-heptyloxy-2- {2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-heptyloxy-2- {2- [trans-4- (trans-4-butylcyclohexylethyl) cyclohexyl] ethyl} pyridine
5-heptyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclohexyl] ethyl} pyridine

Beispiel 5Example 5

Zu einer Suspension von 0,1 mol 5-Hydroxy-2-[2-(trans-4- pentylcyclohexyl)ethyl]-pyridin (Darstellung analog Beispiel 1) 0,1 mol 4-Pentyloxybenzoesäure und einer katalytischen Menge DMAP in 200 ml Ch₂Cl₂ gibt man bei 0°-5° eine Lösung von 18,2 g DCC in 50 ml CH₂Cl₂.To a suspension of 0.1 mol of 5-hydroxy-2- [2- (trans-4- pentylcyclohexyl) ethyl] pyridine (representation analogous to Example 1) 0.1 mol of 4-pentyloxybenzoic acid and a catalytic Amount of DMAP in 200 ml of Ch₂Cl₂ is given at 0 ° -5 ° a solution of 18.2 g DCC in 50 ml CH₂Cl₂.

Man rührt 12 Stunden bei Raumtemperatur, filtriert ab und arbeitet das Filtrat wie üblich auf. Nach Reinigung durch Kristallisation erhält man 4-Pentyloxy-benzoesäure-{2-[2- (trans-4-pentylcyclohexyl)ethyl]-pyridin-5-yl}ester.The mixture is stirred at room temperature for 12 hours, filtered off and works up the filtrate as usual. After cleaning through Crystallization gives 4-pentyloxybenzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester.

Analog werden hergestellt:The following are produced analogously:

4-Pentyloxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Pentyloxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Pentyloxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Pentyloxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Pentyloxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Pentyloxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Pentyloxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Pentyloxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Pentyloxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Pentyloxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Butoxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Butoxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Butoxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Butoxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Butoxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Butoxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Butoxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Butoxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Butoxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Butoxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Butoxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Butoxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Propoxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Propoxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Propoxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Propoxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Propoxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Propoxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Propoxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Propoxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Propoxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Propoxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Propoxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Propoxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Ethoxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Ethoxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Ethoxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Ethoxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Ethoxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Ethoxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Ethoxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Ethoxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Ethoxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Ethoxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Ethoxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Ethoxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Hexyloxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Hexyloxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Hexyloxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Hexyloxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Hexyloxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Hexyloxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Hexyloxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Hexyloxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Hexyloxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Hexyloxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Hexyloxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Hexyloxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Heptyloxy-benzoesäure-{2-[2-(trans-4-ethylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Heptyloxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Heptyloxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Heptyloxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Heptyloxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Heptyloxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester4-Heptyloxy-benzoic acid {2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Heptyloxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Heptyloxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Heptyloxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Heptyloxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Heptyloxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester

4-Octyloxy-benzoesäure-{2-[2-(trans-4-propylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Octyloxy-benzoesäure-{2-[2-(trans-4-butylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Octyloxy-benzoesäure-{2-[2-(trans-4-pentylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Octyloxy-benzoesäure-{2-[2-(trans-4-hexylcyclohexyl)- ethyl]-pyridin-5-yl}ester
4-Octyloxy-benzoesäure-{2-[2-(trans-4-heptylcyclohexyl)- ethyl]-pyridin-5-yl}ester, K 63°S (54°) SC 112° SA 134° N 144° I4-Octyloxy-benzoic acid {2- [2- (trans-4-propylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Octyloxy-benzoic acid {2- [2- (trans-4-butylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Octyloxy-benzoic acid {2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Octyloxy-benzoic acid {2- [2- (trans-4-hexylcyclohexyl) ethyl] pyridin-5-yl} ester
4-Octyloxy-benzoic acid {2- [2- (trans-4-heptylcyclohexyl) ethyl] pyridin-5-yl} ester, K 63 ° S (54 °) S C 112 ° S A 134 ° N 144 ° I.

Beispiel 6Example 6

Analog Beispiel 5 erhält man durch Umsetzung von 5-Hydroxy- 2-[2-(trans-4-pentylcyclohexyl)ethyl]-pyridin und Propionsäure 5-Propylcarbonyloxy-2-[2-(trans-4-pentylcyclohexyl) ethyl]-pyridin.Analogously to Example 5, the reaction of 5-hydroxy 2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridine and propionic acid 5-propylcarbonyloxy-2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridine.

Analog werden hergestellt:The following are produced analogously:

5-Propylcarbonyloxy-2-[2-(trans-4-ethylcyclohexyl)ethyl]- pyridin
5-Propylcarbonyloxy-2-[2-(trans-4-propylcyclohexyl)ethyl]- pyridin
5-Propylcarbonyl-2-[2-(trans-4-butylcyclohexyl)ethyl]- pyridin
5-Ethylcarbonyloxy-2-[2-(trans-4-ethylcyclohexyl)ethyl]- pyridin
5-Ethylcarbonyloxy-2-[2-(trans-4-propylcyclohexyl)ethyl]- pyridin
5-Ethylcarbonyloxy-2-[2-(trans-4-butylcyclohexyl)ethyl]- pyridin
5-Ethylcarbonyloxy-2-[2-(trans-4-pentylcyclohexyl)ethyl]- pyridin5-propylcarbonyloxy-2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridine
5-propylcarbonyloxy-2- [2- (trans-4-propylcyclohexyl) ethyl] pyridine
5-propylcarbonyl-2- [2- (trans-4-butylcyclohexyl) ethyl] pyridine
5-ethylcarbonyloxy-2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridine
5-ethylcarbonyloxy-2- [2- (trans-4-propylcyclohexyl) ethyl] pyridine
5-ethylcarbonyloxy-2- [2- (trans-4-butylcyclohexyl) ethyl] pyridine
5-ethylcarbonyloxy-2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridine

5-Butylcarbonyloxy-2-[2-(trans-4-ethylcyclohexyl)ethyl]- pyridin
5-Butylcarbonyloxy-2-[2-(trans-4-propylcyclohexyl)ethyl]- pyridin
5-Butylcarbonyloxy-2-[2-(trans-4-butylcyclohexyl)ethyl]- pyridin
5-Butylcarbonyloxy-2-[2-(trans-4-pentylcyclohexyl)ethyl]- pyridin5-butylcarbonyloxy-2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridine
5-butylcarbonyloxy-2- [2- (trans-4-propylcyclohexyl) ethyl] pyridine
5-butylcarbonyloxy-2- [2- (trans-4-butylcyclohexyl) ethyl] pyridine
5-butylcarbonyloxy-2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridine

5-Pentylcarbonyloxy-2-[2-(trans-4-ethylcyclohexyl)ethyl]- pyridin
5-Pentylcarbonyloxy-2-[2-(trans-4-propylcyclohexyl)ethyl]- pyridin
5-Pentylcarbonyloxy-2-[2-(trans-4-butylcyclohexyl)ethyl]- pyridin
5-Pentylcarbonyloxy-2-[2-(trans-4-pentylcyclohexyl)ethyl]- pyridin5-pentylcarbonyloxy-2- [2- (trans-4-ethylcyclohexyl) ethyl] pyridine
5-pentylcarbonyloxy-2- [2- (trans-4-propylcyclohexyl) ethyl] pyridine
5-pentylcarbonyloxy-2- [2- (trans-4-butylcyclohexyl) ethyl] pyridine
5-pentylcarbonyloxy-2- [2- (trans-4-pentylcyclohexyl) ethyl] pyridine

5-Pentylcarbonyloxy-2-{2-[trans-4-(trans-4-ethylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Pentylcarbonyloxy-2-{2-[trans-4-(trans-4-propylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Pentylcarbonyloxy-2-{2-[trans-4-(trans-4-butylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Pentylcarbonyloxy-2-{2-[trans-4-(trans-4-pentylcyclo­ hexyl)cyclohexyl]ethyl}pyridin5-pentylcarbonyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexyl) cyclohexyl] ethyl} pyridine
5-pentylcarbonyloxy-2- {2- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] ethyl} pyridine
5-pentylcarbonyloxy-2- {2- [trans-4- (trans-4-butylcyclohexyl) cyclohexyl] ethyl} pyridine
5-pentylcarbonyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] ethyl} pyridine

5-Butylcarbonyloxy-2-{2-[trans-4-(trans-4-ethylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Butylcarbonyloxy-2-{2-[trans-4-(trans-4-propylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Butylcarbonyloxy-2-{2-[trans-4-(trans-4-butylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Butylcarbonyloxy-2-{2-[trans-4-(trans-4-pentylcyclo­ hexyl)cyclohexyl]ethyl}pyridin5-butylcarbonyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexyl) cyclohexyl] ethyl} pyridine
5-butylcarbonyloxy-2- {2- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] ethyl} pyridine
5-butylcarbonyloxy-2- {2- [trans-4- (trans-4-butylcyclohexyl) cyclohexyl] ethyl} pyridine
5-butylcarbonyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] ethyl} pyridine

5-Propylcarbonyloxy-2-{2-[trans-4-(trans-4-ethylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Propylcarbonyloxy-2-{2-[trans-4-(trans-4-propylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Propylcarbonyloxy-2-{2-[trans-4-(trans-4-butylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Propylcarbonyloxy-2-{2-[trans-4-(trans-4-pentylcyclo­ hexyl)cyclohexyl]ethyl}pyridin5-propylcarbonyloxy-2- {2- [trans-4- (trans-4-ethylcyclohexyl) cyclohexyl] ethyl} pyridine
5-propylcarbonyloxy-2- {2- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] ethyl} pyridine
5-propylcarbonyloxy-2- {2- [trans-4- (trans-4-butylcyclohexyl) cyclohexyl] ethyl} pyridine
5-propylcarbonyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] ethyl} pyridine

5-Ethylcarbonyloxy-2-{2-[trans-4-(trans-4-ethylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Ethylcarbonyloxy-2-{2-[trans-4-(trans-4-propylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Ethylcarbonyloxy-2-{2-[trans-4-(trans-4-butylcyclo­ hexyl)cyclohexyl]ethyl}pyridin
5-Ethylcarbonyloxy-2-{2-[trans-4-(trans-4-pentylcyclo­ hexyl)cyclohexyl]ethyl}pyridin5-ethylcarbonyloxy-2- {2- [trans-4- (trans-4-ethylcyclo hexyl) cyclohexyl] ethyl} pyridine
5-ethylcarbonyloxy-2- {2- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] ethyl} pyridine
5-ethylcarbonyloxy-2- {2- [trans-4- (trans-4-butylcyclohexyl) cyclohexyl] ethyl} pyridine
5-ethylcarbonyloxy-2- {2- [trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] ethyl} pyridine

Beispiel 7Example 7

Durch selektive Alkylierung von 2-Methyl-5-pentyl-pyridin mit Lithiumdiisopropylamid in THF bei -30° (analog Bsp. 3b) mit trans-4-(trans-4-Ethylcyclohexylethyl)-cyclohexyl­ o methyliodid erhält man 5-Pentyl-2-[trans-4-(trans-4-ethyl­ cyclohexylethyl)-cyclohexylethyl]-pyridin.By selective alkylation of 2-methyl-5-pentyl-pyridine with lithium diisopropylamide in THF at -30 ° (as in example 3b) with trans-4- (trans-4-ethylcyclohexylethyl) cyclohexyl o Methyl iodide gives 5-pentyl-2- [trans-4- (trans-4-ethyl cyclohexylethyl) cyclohexylethyl] pyridine.

Analog werden hergestellt:The following are produced analogously:

5-Butyl-2-[trans-4-(trans-4-ethylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Propyl-2-[trans-4-(trans-4-ethylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Ethyl-2-[trans-4-(trans-4-ethylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Hexyl-2-[trans-4-(trans-4-ethylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Heptyl-2-[trans-4-(trans-4-ethylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin5-butyl-2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclo hexylethyl) pyridine
5-propyl-2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclo hexylethyl) pyridine
5-ethyl-2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclo hexylethyl) pyridine
5-Hexyl-2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclo hexylethyl) pyridine
5-heptyl-2- [trans-4- (trans-4-ethylcyclohexylethyl) cyclo hexylethyl) pyridine

5-Ethyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Propyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Butyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Pentyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Hexyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Heptyl-2-[trans-4-(trans-4-propylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin5-ethyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclo hexylethyl) pyridine
5-propyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclo hexylethyl) pyridine
5-butyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclo hexylethyl) pyridine
5-pentyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclohexylethyl) pyridine
5-Hexyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclo hexylethyl) pyridine
5-heptyl-2- [trans-4- (trans-4-propylcyclohexylethyl) cyclo hexylethyl) pyridine

5-Ethyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Propyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Butyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Pentyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Hexyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Heptyl-2-[trans-4-(trans-4-butylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin5-ethyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine
5-propyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine
5-butyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine
5-pentyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine
5-Hexyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine
5-heptyl-2- [trans-4- (trans-4-butylcyclohexylethyl) cyclo hexylethyl) pyridine

5-Ethyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Propyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Butyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Pentyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Hexyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin
5-Heptyl-2-[trans-4-(trans-4-pentylcyclohexylethyl)-cyclo­ hexylethyl)-pyridin5-ethyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine
5-propyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine
5-butyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine
5-pentyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine
5-Hexyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine
5-heptyl-2- [trans-4- (trans-4-pentylcyclohexylethyl) cyclo hexylethyl) pyridine

Folgende Beispiele betreffen erfindungsgemäße flüssigkristalline Phasen.The following examples relate to liquid-crystalline according to the invention Phases.

Beispiel AExample A

Eine flüssigkristalline Phase, bestehend ausA liquid crystalline phase consisting of

12% 4-(trans-4-Propylcyclohexyl)-benzonitril,
 8% 4-(trans-4-Butylcyclohexyl)-benzonitril,
13% trans-4-(4-Ethoxyphenyl)-1-propylcyclohexan,
11% trans-4-(4-Butoxyphenyl)-1-propylcyclohexan,
 8% trans-4-(4-Ethoxyphenyl)-1-butylcyclohexan,
 9% trans-4-(4-Methoxyphenyl)-1-pentylcyclohexan,
 5% trans-4-(4-Ethoxyphenyl)-1-pentylcyclohexan,
 5% trans-4-(trans-4-Propylcyclohexan)cyclohexancarbonsäure- (4-propylphenyl)ester,
 5% trans-4-(trans-4-Propylcyclohexyl)cyclohexancarbonsäure- (2-pentylpyridin-5-yl)ester,
 5% trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (4-propylphenyl)ester,
 5% trans-4-(trans-4-Butylcyclohexyl)cyclohexancarbonsäure- (2-pentylpyridin-5-yl)ester,
 4% 4,4′-Bis-(trans-4-propylcyclohexyl)-biphenyl,
 5% 4,4′-Bis-(trans-4-pentylcyclohexyl)-biphenyl und
 5% 4-(trans-4-Pentylcyclohexyl)-4′-(trans-4-propylcyclohexyl)- biphenyl12% 4- (trans-4-propylcyclohexyl) benzonitrile,
8% 4- (trans-4-butylcyclohexyl) benzonitrile,
13% trans-4- (4-ethoxyphenyl) -1-propylcyclohexane,
11% trans-4- (4-butoxyphenyl) -1-propylcyclohexane,
8% trans-4- (4-ethoxyphenyl) -1-butylcyclohexane,
9% trans-4- (4-methoxyphenyl) -1-pentylcyclohexane,
5% trans-4- (4-ethoxyphenyl) -1-pentylcyclohexane,
5% trans-4- (trans-4-propylcyclohexane) cyclohexane carboxylic acid (4-propylphenyl) ester,
5% trans-4- (trans-4-propylcyclohexyl) cyclohexane carboxylic acid (2-pentylpyridin-5-yl) ester,
5% trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (4-propylphenyl) ester,
5% trans-4- (trans-4-butylcyclohexyl) cyclohexane carboxylic acid (2-pentylpyridin-5-yl) ester,
4% 4,4'-bis (trans-4-propylcyclohexyl) biphenyl,
5% 4,4'-bis (trans-4-pentylcyclohexyl) biphenyl and
5% 4- (trans-4-pentylcyclohexyl) -4 ′ - (trans-4-propylcyclohexyl) biphenyl

hat einen Klärpunkt von 90° und eine Viskosität von 19 mm²/s (bei 20°).has a clearing point of 90 ° and a viscosity of 19 mm² / s (at 20 °).

Claims (4)

1. Pyridinderivate der Formel I worin
R¹ und R² jeweils unabhängig voneinander einen Alkylrest mit 1-15 C-Atomen oder einen Alkenylrest mit 2-15 C-Atomen, wobei in diesen Resten auch eine CH₂-Gruppe durch -O-, -CO-, -O-CO- oder -CO-O- ersetzt sein kann, Z¹ -CH₂CH₂ oder eine Einfachbindung,
A¹ -O-CO-Phe-,
Phe unsubstituiertes oder ein- oder mehrfach durch F- und/oder Cl-Atome und/oder CH₃- und/oder CN-Gruppen substituiertes 1,4- Phenylen,
n 0 oder 1 und
m 0 oder 1
bedeutet,
mit der Maßgabe, daß im Falle R² = -O-COAlkyl und/oder m = 1 und/oder
Z¹ = -CH₂CH₂- ist.1. Pyridine derivatives of the formula I. wherein
R¹ and R² each independently of one another an alkyl radical with 1-15 C atoms or an alkenyl radical with 2-15 C atoms, in these radicals also a CH₂ group by -O-, -CO-, -O-CO- or -CO-O- can be replaced, Z¹ -CH₂CH₂ or a single bond,
A¹ -O-CO-Phe-,
Phe 1,4-phenylene which is unsubstituted or mono- or polysubstituted by F and / or Cl atoms and / or CH₃ and / or CN groups,
n 0 or 1 and
m 0 or 1
means
with the proviso that in the case R² = -O-COalkyl and / or m = 1 and / or
Z¹ = -CH₂CH₂- is. 2. Verwendung der Verbindungen der Formel I nach Anspruch 1 als Komponenten flüssigkristalliner Phasen.2. Use of the compounds of formula I according to claim 1 as components of liquid crystalline phases. 3. Flüssigkristalline Phase mit mindestens zwei flüssigkristallinen Komponenten, dadurch gekennzeichnet, daß mindestens eine Komponente eine Verbindung der Formel I ist.3. Liquid crystalline phase with at least two liquid crystalline phases Components, characterized in that at least one component connects the Formula I is. 4. Flüssigkristallanzeigeelemente, dadurch gekennzeichnet, daß es eine Phase nach Anspruch 4 enthält.4. liquid crystal display elements, characterized in that it contains a phase according to claim 4.
DE3814346A 1988-04-28 1988-04-28 PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME Withdrawn DE3814346A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE3814346A DE3814346A1 (en) 1988-04-28 1988-04-28 PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME
JP1504480A JPH02504035A (en) 1988-04-28 1989-04-15 Pyridine derivative
PCT/EP1989/000408 WO1989010356A1 (en) 1988-04-28 1989-04-15 Pyridine derivatives
EP89904791A EP0365641A1 (en) 1988-04-28 1989-04-15 Pyridine derivatives
CN89102622A CN1037334A (en) 1988-04-28 1989-04-26 Pyridine derivate
DD89327988A DD283833A5 (en) 1988-04-28 1989-04-26 LIQUID CRYSTALLINE PHASE WITH AT LEAST TWO LIQUID CRYSTALLINE COMPONENTS
KR1019890702461A KR900700453A (en) 1988-04-28 1989-12-27 Pyridine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE3814346A DE3814346A1 (en) 1988-04-28 1988-04-28 PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME

Publications (1)

Publication Number Publication Date
DE3814346A1 true DE3814346A1 (en) 1989-11-09

Family

ID=6353084

Family Applications (1)

Application Number Title Priority Date Filing Date
DE3814346A Withdrawn DE3814346A1 (en) 1988-04-28 1988-04-28 PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME

Country Status (7)

Country Link
EP (1) EP0365641A1 (en)
JP (1) JPH02504035A (en)
KR (1) KR900700453A (en)
CN (1) CN1037334A (en)
DD (1) DD283833A5 (en)
DE (1) DE3814346A1 (en)
WO (1) WO1989010356A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991004249A1 (en) * 1989-09-22 1991-04-04 MERCK Patent Gesellschaft mit beschränkter Haftung Pyridine derivatives and a liquid crystal medium

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5145601A (en) * 1990-06-25 1992-09-08 The University Of Colorado Foundation Inc. Ferroelectric liquid crystals with nicotinic acid cores
CN101130466B (en) 2006-08-23 2011-05-04 中国科学院大连化学物理研究所 Method of start working of fluidization catalytic reaction device for preparing low carbon olefinic hydrocarbon
CN104108726B (en) * 2013-04-16 2017-08-11 中国石油化工股份有限公司 High silica alumina ratio CHA structure silicoaluminophosphamolecular molecular sieves and its synthetic method

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH645664A5 (en) * 1980-12-16 1984-10-15 Merck Patent Gmbh LIQUID CRYSTAL MIXTURE.
EP0056501B1 (en) * 1981-01-19 1984-05-02 MERCK PATENT GmbH Liquid crystal mixture
EP0164721A3 (en) * 1984-06-13 1986-02-26 Chisso Corporation Novel liquid crystal compound and liquid crystal composition containing same
EP0168683B1 (en) * 1984-07-16 1990-11-28 F. Hoffmann-La Roche Ag Liquid crystals with alkenyl or alkenyloxy groups

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991004249A1 (en) * 1989-09-22 1991-04-04 MERCK Patent Gesellschaft mit beschränkter Haftung Pyridine derivatives and a liquid crystal medium

Also Published As

Publication number Publication date
CN1037334A (en) 1989-11-22
EP0365641A1 (en) 1990-05-02
WO1989010356A1 (en) 1989-11-02
DD283833A5 (en) 1990-10-24
KR900700453A (en) 1990-08-13
JPH02504035A (en) 1990-11-22

Similar Documents

Publication Publication Date Title
EP0334911B1 (en) Substituted phenyltrifluormethylethers
EP0264435B1 (en) Smectic liquid crystal phases
EP0364538B1 (en) Difluorobenzol derivatives
EP0313604B1 (en) Electro-optical liquid crystal display element
EP0306521B1 (en) Ethine derivatives as compounds of liquid crystal phases
EP0256097B1 (en) Vinyl compounds and liquid crystal phase
EP0138006A2 (en) Liquid-crystal phase
EP0182054A2 (en) Heterocyclic compounds
EP0168043A2 (en) Liquid crystal phase
EP0362318B1 (en) 2,3-difluorobiphenyls
DD241423A5 (en) LIQUID CRYSTALLINE PHASE CONTAINING PYRIMIDINE
DE3721268A1 (en) ARYL SULFUR PENTAFLUORIDE
EP0373191B1 (en) Heterocyclic 1,2-difluorobenzene derivatives
EP0158137A2 (en) Pyrimidines
DD254590A5 (en) CHIRAL-TREATED SMEKTIC LIQUID CRYSTALLINE PHASE
EP0220254B1 (en) Benzonitriles
DE4409431A1 (en) Cyanophenylpyri(mi)dine derivatives, and liquid-crystalline medium
EP0135062B1 (en) Cyclohexyldioxanes
DE3807957A1 (en) DERIVATIVES OF 2,3-DIFLUORPHENOL
EP0358741A1 (en) Derivatives of 2,3-difluorobenzoic acid.
DE3814346A1 (en) PYRIDE DERIVATIVES, THEIR USE AS COMPONENT LIQUID CRYSTAL PHASES, THE CORRESPONDING LIQUID CRYSTAL PHASES AND THE LIQUID CRYSTAL DISPLAY ELEMENTS CONTAINING THE SAME
EP0441933B1 (en) Difluorobenzonitriles and liquid-crystal medium
DE3443929A1 (en) CARBONITRILE
DE4410606B4 (en) Cyanopyrimidine derivatives and liquid crystalline medium
DE3731619A1 (en) Nitrogen-containing compounds for use in liquid-crystalline mixtures

Legal Events

Date Code Title Description
8139 Disposal/non-payment of the annual fee