CA2510394C - Decahydronaphthalene derivative - Google Patents

Abstract

The present invention discloses a decahydronaphthalene derivative represented by general formula (I): (see formula I) a liquid crystal composition in which it is contained, and a liquid crystal device in which it is used. The novel decahydronaphthalene derivative of the present invention can be produced industrially extremely easily as shown in the examples, and by adding a small amount to a base liquid crystal, it is possible to have effects that expand the nematic phase temperature range, thereby improving its various characteristics as a nematic liquid crystal. Moreover, the novel decahydronaphthalene derivative of the present invention also has superior co-solubility with base liquid crystals generally used at present. Thus, it is suitable for various types of liquid crystal devices requiring a wide operating temperature range, and is extremely useful as a liquid crystal material.

Description

D~TNQ~itiDES OU BREVETS VOLL~~~INEUX
LA PRESENTE PARTIE DE CETTE DEibU~NDE OU CE BREti7ETS
COI'VIPREND PLUS D'UN TOME.

CECI EST LE TONIE j DE 'g NOTE: Pour les tomes additioneis, veillez contacter le Bureau Canadien des Brevets.

.1LTNIBO APPLICATIONS / PATENTS

THIS SECTION OF THE APPLICATION / PATENT CCiNTAt~(S MORE
THAN ONE VOLUME.

THIS IS VOLUIYLE OF ~

NOTE: For additional volumes olease contact the Canadian Patent Office.

DESCRIPTION
DECAHYDRONAPHTHALENE DERIVATIVE
TECHNICAL FIELD

The present invention relates to a decahydronaphthalene derivative, which is a novel liquid crystal compound, and a liquid crystal composition containing said derivative. This derivative is useful as a liquid crystal material for -electrooptical liquid crystal display, and has a wide temperature range in particular.

BACKGROUND ART

Liquid crystal display elements have come to be used in not only clocks and calculators, but also in various types of measuring instruments, automobile instrument panels, word processors, Personal Digital Assistants, printers, computers and televisions. Typical examples of liquid crystal display methods include TN (twisted nematic) types, STN (super twisted nematic) types, DS (dynamic scattering) types, GH (guest host) types and FLC (ferroelectric liquid crystal) types. In addition, multiplex driving instead of the conventional static driving has become the most common type of driving method.
Moreover, simple matrix types, and more recently, active matrix types, have come into practical use.

Liquid crystal materials are required to have various characteristics to accommodate these display and driving methods. Although a wide temperature range is extremely important in nearly all cases, this includes that in which the nematic phase upper limit temperature (TN_I) is sufficiently high, and the melting point (TC-N) or the smectic-nematic transition temperature (TS_N) is sufficiently low.

In addition, co-solubility with other liquid crystal compounds and versatile liquid crystal compositions is also important. If this co-solubility was defective, it became necessary to mix extremely many kinds of liquid crystal compounds in order to avoid the risk of precipitation and phase separation, making compound preparation extremely bothersome and making increased costs unavoidable.

In addition, a sufficiently low driving voltage is also an important characteristic in many cases, and it is necessary for the threshold voltage (Vth) to be low in order to accomplish this.

In addition, rapid response is also an equally important characteristic, and the viscosity of the liquid crystal is required to be as low as possible in order to accomplish this.

In addition, birefringence (On) is also an important characteristic. Although various values are required according to the display method, a low value is frequently required in the case of liquid crystal devices having a large cell thickness for easy manufacturing.

Although an extremely large number of liquid crystal compounds have been synthesized in the past in order to satisfy these requirements, not all of the problems were able to be solved. Thus, there is a need for a liquid crystal compound having superior characteristics with respect to each of the above requirements.

In general, liquid crystal compounds are formed from a central skeleton (core) portion and side groups (side chains and polar groups). There are numerous known examples of the ring structure that composes the core portion, such as a 1,4-phenylene group (which may be substituted with fluorine) and trans-l,4-cyclohexylene group, as well as heterocyclic aromatics such as a pyridine-2,5-diyl group and pyrimidne-2,5-diyl group, and saturated heterocyclic rings such as a dioxane-trans-l,4-diyl group and piperidine-l,4-diyl group.
However, this ring structure is practically limited to a 1,4-phenylene group (which may be substituted with fluorine), trans-l,4-cyclohexylene group and a small number of heterocyclic aromatics. However, liquid crystal compounds composed of these ring structures alone are currently unable to adequately accommodate the characteristics required of increasingly sophisticated liquid crystal compounds.

Since compounds containing a trans-2,6-trans-decahydronaphthalene group are saturated rings that do not contain hetero atoms such as oxygen atoms or nitrogen atoms, in addition to being expected to demonstrate superior stability, they are also expected to improve liquid crystal properties. However, there have been few examples of trans-2,6-trans-decahydronaphthalene derivatives reported thus far (W. Sucrow and H. Wolter, Chimia, 36, 460 (1982); Mol. Cryst.

Lig. Cryst., 95, 63 (1983)), and hardly anything is known regarding their characteristics.

DISCLOSURE OF THE INVENTION
The problem to be solved by the present invention is to provide a novel liquid crystal composition in the form of a decahydronaphthalene derivative, and to provide a liquid crystal composition suitable for STN or TFT driving that uses any of these derivatives, has a wide nematic phase temperature range, has a low birefringence, and is able to be driven at a low voltage and respond rapidly.
In accordance with one aspect of the present invention, there is provided a compound represented by general formula (II) :

m b~=o ' (wherein, R4 represents an alkyl group, alkoxy group, alkenyl group, alkenyloxy group or alkoxyalkyl group, L1 represents -CH2CH2-, -CH (CH3) CHz-, -CHzCH (CH3) -, -CH2O-, -OCH2-, -CFZ0-, -OCF2-, -COO-, -OCO-, -CH=CH-, -CF=CF-, -C=-C-, -O(CHZ)3-, -(CH2)3O-, -(CH2)4- or a single bond, R4 represents an alkenyl group, alkenyloxy group or alkoxyalkyl group when L1 represents a single bond, ring A and m are the same as defined in general formula (I), and the decahydronaphthalene ring has a trans form).
In accordance with another aspect of the present invention, there is provided a compound represented by general formula (V-2):

Ul -a L
U2 (V-2) (wherein, U1 and U2 respectively and independently represent an oxygen atom or the following structure:

(CH2)k % 0 (wherein, k represents an integer from 1 to 7) , L is the same as previously defined in general formula (I), and the decahydronaphthalene ring has a trans form).

5 In accordance with an aspect, there is provided a compound represented by general formula (II):

m O (II) wherein, R4 represents an alkyl group, alkoxy group, alkenyl group, alkenyloxy group or alkoxyalkyl group, L1 represents - CH2CH2 - , - CH ( CH3 ) CHz - , - CH2CH ( CH3 ) - , - CH2O - , - OCH2 - , -CF2 0 - , -OCF2-, -COO-, -OCO-, -CH=CH-, -CF=CF-, -C=C-, -O(CH2)3-, -(CHZ) 30-, -(CH2) 4- or a single bond, wherein R4 represents an alkenyl group, alkenyloxy group or alkoxyalkyl group when L1 represents a single bond, ring A represents a trans-1, 4-cyclohexylene group in which one CH2 group or more than one non-adjacent CH2 groups in the group is optionally replaced by -0- or -S-, a 1,4-phenylene group in which one CH2 group or more than one non-adjacent CH2 groups in the group is optionally replaced by -N=, a 1,4-cyclohexenylene group, a 1,4-bicyclo(2,2,2)octylene group, a piperidine-l,4-diyl group, a naphthalene-2,6-diyl group, a trans-decahydronaphthalene-trans-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and is optionally substituted with a cyano group or halogen, m represents an integer of 1 or 2, and the decahydronaphthalene ring has a trans form.

In accordance with another aspect, there is provided a production method of general formula (II) comprising: reducing a compound represented by general formula (II-A):

R4 E L' O (II-A) m OH

5a wherein, R4 is the same as previously defined in general formula (II), ring E represents a 1,4-phenylene group or trans-1,4-cyclohexylene group, L1 and m are the same as previously defined in general formula (II), and the decahydronaphthalene ring has a trans form, and oxidizing the hydroxyl group as necessary.
In accordance with still another aspect, there is provided a compound represented by general formula (V-2):

U,-a L, U2 (V-2) wherein, U1 and U2 independently represent an oxygen atom or the following structure:

= 0 (CH2)k N O

wherein, k represents an integer from 1 to 7, L1 is the same as previously defined in general formula (II), and the decahydronaphthalene ring has a trans form.
In accordance with a further aspect, there is provided a production method of general formula (V-2) or general formula (V-1) :

Ul U2 (V-1) wherein Ul and U2 independently represent an oxygen atom or the following structure:

=0 (CH2)k , 0 5b wherein, k represents an integer from 1 to 7, L1 is the same as previously defined in general formula (II), and the decahydronaphthalene ring has a trans form the method comprising: reacting a compound represented by general formula (V-lA) or general formula (V-2A):

O
(CH2)k ~~ L -t&O (V-2A) (CH2)O O (V-1 A) O
. O >&

wherein, k is the same as previously defined in general formula (V-2), and Ll is the same as previously defined in general formula (II) with a secondary amine to form an enamine, and reacting said enamine with methyl vinyl ketone to obtain a compound represented by general formula (V-1B) or general formula (V-2B) :

O
O
(CH2)k (CH2)k ~~L.L
`O O (V-1 B) 0 ,~~_,,~_// O (V-26) wherein, k is the same as previously defined in general formula (V-2), and L1 is the same as previously defined in general formula (II) followed by reductive hydrogenation.
In accordance with still a further aspect, there is provided a production method of general formula (V-1) comprising: reducing a compound represented by formula (V-1C) by hydrogenation in the presence of metal catalyst:

HO
OH (V-1 C) oxidizing the hydroxyl groups as necessary, and protecting the carbonyl groups as necessary.
In accordance with still a further aspect, there is provided a production method of general formula (V-2) 5c comprising: reducing a compound represented by general formula (V-2C) F ~' G
(V-2C) wherein, L1 is the same as previously defined in general formula (II), although ring G represents a cyclohexane ring or benzene ring, a single bond(s) of the cyclohexane ring is optionally replaced by double bond(s), and although rings F and H
respectively and independently represent the following structures:

Ui~ HO-{( ) HO-0 wherein, U1 is the same as previously defined in general formula (V-1) or general formula (V-2), a single bond(s) of the cyclohexane ring is optionally replaced by double bond(s), oxidizing the hydroxyl group as necessary, and further protecting the carbonyl group as necessary.
In accordance to still a further aspect, there is provided a production method of general formula (V-la):

O
(CH2)k `O O (V-1 a) wherein, k is the same as previously defined in general formula (V-1) or general formula (V-2), comprising monoacetalation of a compound represented by general formula (V-1D):

o (V-1 D) In order to solve the above problems, the present 5d invention in one aspect provides a novel liquid crystal compound in the form of a decahydronaphthalene derivative represented by general formula (I).

BEST MODE FOR CARRYING OUT THE INVENTION
The following provides a detailed explanation of the present invention. A compound of general formula (I) provided in the present invention is preferably of the form described below.
In general formula (I), although R and Z represent alkyl groups or alkoxy groups having 1-16 carbon atoms, alkenyl groups having 2-16 carbon atoms, alkenyloxy groups having 3-16 carbon atoms, alkyl groups having 1-12 carbon atoms substituted with alkoxy group(s) having 1-10 carbon atoms, hydrogen atoms, fluorine atoms, chlorine atoms, trifluoromethoxy groups, difluoromethoxy groups, trifluoromethyl groups, 2, 2, 2-trifluoroethoxy groups, cyano groups, cyanato groups, hydroxyl groups or carboxyl groups, which may be substituted with halogen(s), a straight chain alkyl group having 1-12 carbon atoms or a straight chain alkenyl group having 2-12 carbon atoms is preferable, a straight chain alkyl group having 1-7 carbon atoms or a straight chain alkenyl group having 2-7 carbon atoms is more preferable and the following structures are particularly preferable for R in the case of a straight chain alkenyl group:
, /-\- ,-X_ ,\\- -/-N-(wherein, the right side is linked to a ring); a structure similar to that in R is preferable for Z in the case the dielectric anisotropy of the compound is near 0 or negative, and a fluorine atom, chlorine atom, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group, 2, 2, 2-trifluoroethoxy group or cyano group is preferable, a fluorine atom, trifluoromethoxy group or cyano group is more preferable, and a fluorine atom or cyano group is particularly preferable for Z in the case the dielectric anisotropy of the compound is positive. Although m and n respectively and independently represent an integer from 0 to 2 and satisfy m+ n<_ 3, they are preferably respectively and independently 0 or 1, and more preferably satisfy 1 S m + n S 2. Ring A and ring B when present may be the same or different, represent a trans-1, 4-cyclohexylene group wherein one CH2 group or more than one adjacent CH2 groups in the group may be replaced by -0- or -S-, or a 1,4-phenylene group, 1,4-cyclohexenylene group, 1, 4-bicylo(2,2,2)octylene group, piperidine-l,4-diyl group, naphthalene-2, 6-diyl group, trans-decahydronaphthalene-trans-2, 6-diyl group or 1,2,3,4-tetrahydronaphthalene-2, 6-diyl group wherein one CH group or more than one adjacent CH groups in the group may be replaced by -N=, and although these may be substituted with a cyano group or halogen, a 1,4-phenylene group or trans-l,4-cyclohexylene group that may be substituted with halogen is preferable, a trans-1,4-cyclohexylene group is more preferable for ring A, and a 1,4-phenylene group, 3-fluoro-l, 4-phenylene group, 3, 5-difluorol-1, 4-phenylene group or trans-1,4-cyclohexylene group is more preferable for ring B. Although L and M when present may be the same or different, and represent different, and represent -CH2CH2-, -CH (CH3) CH2-, -CHzCH (CH3) -, -CHzO-, -OCH2-, -CF2O-, -OCF2-, -COO-, -OCO-, -CH=CH-, -CF=CF-, -C=C-, -0 (CH2) 3-, -(CH2) 30-, -(CHz) 9- or a single bond, -CH2CH2- or a single bond is preferable for L while a single bond is particularly preferable, and -COO-, -OCO-, -CH2CH2-, -C
= C- or a single bond is preferable for M, while a single bond is particularly preferable.

As has been described above, although the compound of general formula (I) includes an extremely large number of types of compounds according to the selection of its R. ring A, ring B, L, M, m, n and Z, each of the compounds represented by general formulas (Iaa) through (Ihx) below is particularly preferable.

R F (laj) R O F (laa) F R F (lak) R O F (lab) F R F (lal) R O F (lac) F
F
R OCF3 (lam) -0 R O OCF3 (lad) F
F OCF3 (Ian) R
O OCF3 (lae) R F

R F OCF3 (lao) ~F3 (la~ R F
F
CN (lap) R' R
O CN (la9) F
F R CN (laq) R
CN (lah) R F CN (lar) CN (lai) R F

F
Rl O
COZ CN (las) F
-(( )}-CN (lat) R C0Z ~/

F
R CO2O CN (lau) F

R O R O F
F (Iba) (Ibj) F
F F (Ibk) R
O F (ibb) R F
R F
R F (ibi) F (IbC) F
F
R R O OCF3 (ibm) O OCF3 (Ibd) F
F
R O R O
OCF3 (Ibe) OCF3 (Ibn) F
R R OCF3 (Ibo) OCF3 (Ibfl F
F

-c ~ I O CN (Ib9) O CN (Ibp) R

F
F
R O CN (Ibh) R CN (Ib4) F
F
R CN O R CN (Ibr) Ibi F
F

COZ--~-CN (Ibs) ~F

R COZ---(( }}-CN (Ibt) ~JF
R
Cp2 4CN (Ibu) F

R R
O O F (Ica) O O OCF3 (Icm) F
R R
O O F (Icb) O O OCF3 (Icn) F F
R R O O (ICO) O --(( )}-F (Icc) OCF3 F F F F
R O O R
F (Icd) O O OCF3 (IcP) F F F F
R O O R
F (Ice) O O OCF3 (Icq) F F F F
R R
O O F (Icfl O O OCF3 (Icr) F F F F

R O O F (Icg) R O O OCF3 (Ics) F F
F F F F
R R
O O F (Ich) O O OCF3 (Ict) F F
F F F F
R
O O F (Ici) O O OCF3 (Icu) F F F F

R O F (Icl) R O OCF3 (Icv) F F
R O R
F (Ick) O pCF3 (Icv,,) F F
R F (ICI) R
OCF3 (ICx) F F

R O O CN (Ida) COz O O CN (Idm) F F
R O O CN (Idb) COz ~ CN (Idn) F F
R O O CN (IdC) R COz O O CN (Ido) F F F F

R O O R CN (Idd) C02 O O CN (idp) F F F F __C) R O O CN (ide) R aC02-6-6-CN (Idq) F F F F
R
O O CN (Idf) aCO2--~O O CN (Idr) F F F F

R
--c R CN (1ds) O O CN (Idg) CO2-0O
F F
F F F

R O O CN (Idh) R C02 6O CN (Idt) F F
R F F F
O O CN (idi) R COZ O O CN (Idu) F F F F

R O CN (Idj) R CO2-{( )}-CN (Idv) F ~F
-"(::) R O CN (Idk) R Cp2_,_(~1~--CN (idw) ~/ F

R CN (Idl) R CO2 4CN (Idx) F F

R O = O F (lea) R O = O OCF3 (1el) -c~
F
O F (leb) R O = O OCF3 (lek) R

F R
R -_ O F (lec) 1l-OCF3 (lel) F F
F F
O = O OCF3 (lem) R O = O F (led) R
-0~
-c~ F
R O O F (lee) R OCFs (len) = t~ _ F F

F
F F
_ O F (lef) R O = O OCFs (leo) F F
F F
R O =
R F (leg) O OCF3 (lep) O __ O
F
-c~
F F F
F F
F (leh) R O = O OCF3 (Ieq) R
F
F F
R O __ O F (lei) R O .- OCF3 (ler) F F O
F
F

R O
R O
F (Ifa) F (Ifj) R
R O O
F (Ifb) F (Ifk) O O
R F O
O O (Ifl) F (Ifc) F
F R F
F F
R O O
OCF3 (Ifd) OCF3 (Ifm) R F
R F O
O O OCF3 (Ife) OCF3 (Ifn) F
R F
OCF3 (Iff) R O O OCF3 (Ifo) F F
F R
R
CN (Ifg) CN (IfP) F
F
R F
-0 CN (Ifh) R O O CN (Ifq) F
R R F
CN (Ifi) O O CN (Ifr) F
F

R R
F (Iga) CF3 (19k) F F
R R F -0 F (Igb) CF3 (191) R F
R
F (Igc) OCF2H (19m) F
R F R

F (Igd) OCF2H (Ign) R F R

OCFa (Ige) OCF2H (Igo) -(:) R F
R F
OCF3 (19~
OCFZH (19P) R F
_ OCF3 (199) R
F CN (Igq) R
O F
OCF3 (Igh) R
CN (Igf) CFa (Igi) CN (19S) F F
R F
cF3 (191) CN (Igt) F

R (Ink) R (Ina) R (Inl) R (Inb) R R (Inc) (Inm) R (Ind) (Inn) R (Ine) R -O~~ (Ino) R (Infl R (Ing) (Inh) (Ini) R (Inl) F
R
R
(toa) (lot) F

R O
(lob) R Q
(lom) F

R O R--( t ) }
(loc) (lon) F
R O R O
(100) (lod) F
R O R O
(loe) --v-- (lop) F F
R O
(lof) R 0 (lo4) F F

(log) R O (lor) F
F F
R O
(loh) R 0 (los) F F
R O
(101) R O
(lot) F F F

b (loj) R O (tou) F F F F

R ~-=- R R O R R O R
(lok) (lov) (low) R O (iPa) R O O R (IPk) F
R O O R (iPi) R (Ipb) F
R F R O O R(Ipm) R (ipC) F F

F R O O R(iPn) R O R (Ipd) F
F
F F R O O R(iPO) R O R (Ipe) F

R O R (iPP) R R (iPfl F
F F (IPq) R O O R
R O R (iP9) F
F
F R O R(ipr) R O R (Iph) F F
F R FO R(iPS) R O R (Ipi) F F
F F
R (Ipt) F F O
R O R (iPJ) R

F
R R(Iqa) R O O R (Iqk) F F

R O R(Iqb) R O O R(Iql) F F F

R (( i}-R (Iqc) R O O R (Iqm) F~/ F F F

R OR (Iqd) R O OR(Iqn) F F F
R R
O R(Iqe) O O R(190) F F

R O O R(Iqf) R O O R(IqP) F F
R O O R (1q9) O R (Iqq) F F F F F
R R
O O R (Iqh) O O R(Iqr) F F F F
R
O O R (Iqi) ~ R (Iqs) F F F F F F F

R R O O R (Iqt) O O R (Iql) F F F

R R (Iqt) R R O F
R (Ira) R (Irm) R R

R(Irb) O O R (Irn) R F R
R(Irc) O O R(Iro) F F
R R
R (Ird) O O R(IrP) F F
R R O F
R (Ire) R (Irq) F F
R
R O
R (Ir~ F
R (irf) F F F F
R ___---O R O F
R (Irg) R (Irs) R O R
R (Irh) O O R (Irt) F
F F
R O R C~
R (Iri) R (Iru) F
R O R
R (IrJ) O R (In1) F F F

R (Irk) O R (Irw) R R O
R O O R (IrI) R O O R (Irx) F
F F F F
R O

R (IrY) F
F

(wherein, although R is the same as previously defined in formula (I), a straight chain alkyl group having 1-7 carbon atoms or a straight chain alkenyl group of the structure shown below is preferable, and although R1 represents an alkenyl 5 group having 2-16 carbon atoms, the following structure is preferable):

(wherein, the right side is linked to a ring).

The following forms are particularly preferable for the compound of general formula (V-1) or general formula (V-2) 10 provided in the present invention:

O
O (V-1 a) 0-3 (V-1 b) ::,:Z: O

O RI

O D (V-1 c) -0& O (V-1 d) (wherein, R' is the same as previously defined, and the decahydronaphthalene ring represents the trans form); and, O (V-2a) O O (V-2e) ~
O O
D (V-2b) (V-2fl C
C
O O (V-2c) (V-2g) O O
~(V-2d) ` O O (V-2h) R O (V-2i) R O (V-2k) R' O (V-2j) R O (V-21) (wherein, although R is the same as previously defined in formula (I), a straight chain alkyl group having 1-7 carbon atoms or a straight chain alkenyl group having the following structure is preferable, R is the same as previously defined, and the decahydronaphthalene ring represents the trans form).
A compound of general formula (I) can be produced based on the steps indicated below. In addition, the production method of the compound of general formula (I) is not limited to the production examples described below.

1. Synthesis of General Formula (I) - 1 1-1 Synthesis of General Formula (Iaf) from General Formula (Iaa) and General Formula (Ibf) from General Formula (Iba) in which R is an Alkyl Group, Alkoxy Group or Alkoxyalkyl Group After reacting a decahydronaphthalene derivative represented by general formula (IIa):

R2--(&L m O (Ila) (wherein, R 2 represents an alkyl group, alkoxy group or alkoxyalkyl group, ring A, m and L are the same as previously defined in general formula (I), and the decahydronaphthaiene ring has a trans form) with organometallic reagent (III):

Za 22 w :0~ zi (u1) (wherein, Z' represents an alkyl group, alkoxy group, alkyl group substituted with an alkoxy group, hydrogen atom, fluorine atom, chlorine atom, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group or 2, 2, 2-trifluoroethoxy group, Z2 Z3 and z 4 respectively and independently represent a hydrogen atom, fluorine atom or chlorine atom, W represents MgX (wherein, X
represents a chlorine atom, bromine atom or iodine atom), a metal atom such as Li, B(OH)2 or SiF(CH3)Z, and these can be easily prepared from the corresponding halogenated benzene derivative), by dehydrating in the presence of acid catalyst, octahydronaphthalene derivative (IV):

~~ ZZ~
R~ ~-t( A r--L m (lv) ~ ~--~

(wherein, R2, L, Z1, Zz, Z3, Z9, ring A and m are the same as previously defined, and the 9,10 positions of the octahydronaphthalene ring have trans forms) is obtained. By hydrogenating the double bond of the octahydronaphthalene ring and isomerizing in the presence of alkaline catalyst as necessary, (IA-1), which includes general formula (Iaf) from general formula (Iaa) and general formula (Ibf) from general formula (Iba):

~/~\ Z4 Z2 R2-{-( A }-L
~ ~! m (wherein, R2, L, Z1, Z2, Z3, Z4, ring A and m are the same as previously defined, and decahydronaphthalene ring has a trans form) can be produced.

1-2 Synthesis of General Formula (Iaf) from General Formula (Iaa) and General Formula (Ibf) from General Formula (Iba) in which R is an Alkenyl Group After reacting a decahydronaphthalene derivative represented by formula (V-lb) or general formula (V-2b):
L
I~X~}-O 0(V-1 b) C~ O(V-2b) (wherein, L is the same as previously defined in general formula (I), and the decahydronaphthalene ring has a trans form) with organometallic reagent (III), by dehydrating in the presence of acid catalyst and re-converting to acetal, general formula (VIa) or general formula (Vib):

c o z4 z2 O Z' (Via) o r (Vib) (wherein, L, ZZ2, Z3 and Z4 are the same as previously defined, and the 9,10 positions of the octahydronaphthalene ring have trans forms) is obtained. After hydrogenating the double bond of the octahydronaphthalene ring and isomerizing in the presence of alkaline catalyst as necessary followed by deacetalization, general formula (VIIa) or general formula (VIIb) :

Z'4 Z2 O
(Vlla) Z" Z2 O=0- L
r (vllb) (wherein, L, Z', Z2, Z3 and Z4 are the same as previously defined, and the 9,10 positions of the octahydronaphthalene ring have trans forms) is obtained. After then reacting this with Wittig's reagent (VIII), Ph3P=CHOCH3 (VIII) it was acid hydrolyzed and isomerized to the trans form using base followed by repeating reaction of (VIII) and acid hydrolysis to obtain alkanal derivative (IX) :

~/~'\ Z'~ Z2 HCO- (CH2i-{{ }-- L
\ ~--/ m 2i (IX) (wherein 1 represents an integer of 0 or greater, m, L, Z1, Zz, Z3 and Z4 are the same as previously defined, and the decahydronaphthalene ring has a trans form). After reacting this with general formula (X):

Ph3P=CHR3 (X) 5 (wherein, R3 represents a hydrogen atom or alkyl group that may be substituted with one or more fluorine atoms or alkoxy groups), by isomerizing the double bond to the trans conformation using a benzene sulfinate and so forth as necessary, decahydronaphthalene derivative (IA-2), in which R

10 of general formula (Iaf) from general formula (Iaa) and general formula (Ibf) from general formula (Iba) represents an alkenyl group:

Z'~ Z2 3-1/ (CH2h~ L m R Z' (IA-2) (wherein, 1 represents an integer of 0 or greater, R3, m, L, Z1, z 2, Z3 and Z4 are the same as previously defined, and the 15 decahydronaphthalene ring has a trans form), can be produced.
In addition, by reducing alkanal derivative (IX) to obtain an alcohol derivative and then converting this to an alkoxide followed by reacting the alkyl halide, a compound can be produced wherein, in general formula (I), n is 1, ring C is a 20 1,4-phenylene group, and R is an alkoxy group, etc.

1-3 Synthesis of General Formula (lao) from General Formula (Iaj) and General Formula (Ibo) from General Formula (Ibj) After reacting Wittig's reagent (VIII) with general formula (IIa), by acid hydrolyzing, isomerizing to the trans form using base, again reacting with (VIII) and repeating acid hydrolysis, and reacting general formula (III) with alkanal derivative (XI):

RZ-~- L CHO
\~J m (XI) (wherein, R2, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), followed by dehydrating in the presence of acid catalyst, decahydronaphthalene derivative (XII):

R2-t~A~...~ ,-L Z, (XII) \

(wherein, R2, L, Z1, ZZ, Z3, Z4 , ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) is obtained. By hydrogenating the double bond, (IA-3), which includes general formula (Iao) from general formula (Iaj) and general formula (Ibo) from general formula (Ibj)=

R2-~-L Z3 r (IA-3) ~~-' (wherein, R2, L, Z1, Z2, Z3, Z4 , ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) can be produced.

1-4 Synthesis of General Formula (Iai) from General Formula (Iag), General Formula (Iar) from General Formula (Iap), General Formula (Ibi) from General Formula (Ibg) and General Formula (Ibr) from General Formula (Ibp) After either direct bromination or iodination or lithionation with alkyl lithium of a phenyldecahydro-naphthalene derivative represented by general formula (XIII) for which the synthesis method has already been described:
e Z2 R~q~-- L
\ ~--J ymcz:~ Ml (XIII) (wherein, R, L, Z2, Z3, Z9, ring A and m are the same as previously defined, M1 represents a single bond or an alkylene group having 1-4 carbon atoms, and the decahydronaphthalene ring has a trans form), by reacting with bromine or iodine, '15 decahydronaphthalene derivative (XIV):
Zd Z2 ~q~
~ ~J m My O Ze (XIV) (wherein, Z5 represents a halogen atom such as bromine or iodine, R, L, Z2, Z3, Z9, ring A and m are the same as previously defined, M1 represents a single bond or alkylene group having 1-4 carbon atoms, and the decahydronaphthalene ring has a trans form) can be produced.
Organometallic reagent (XV):

zz m za R AL
Ml W, (XV) z3 (wherein, W1 represents a metal such as MgBr, MgI or Li or a metal-containing group, R, L, Z2, Z3, Z4 , ring A and m are the same as previously defined, M1 represents a single bond or an alkylene group having 1-4 carbon atoms, and the decahydronaphthalene ring has a trans form) is produced by reacting a metal such as magnesium with general formula (XIV) or by converting general formula (XIII) to the trans-metal using an organometallic reagent such as alkyl lithium. By reacting this with- carbon -dioxide, -a benzoic.acid derivative represented by general formula (XVI):
Z~ Z2 ` ~--1 m MI :OL C02H (XVI) (wherein, R, L, Z2, Z3, Z4, ring A and m are the same as previously defined, M1 represents a single bond or an alkylene group having 1-4 carbon atoms, and the decahydronaphthalene ring has a trans form) is obtained. After converting this to an acid halide with a halogenating agent such as thionyl halide, by reacting with ammonia to convert an acid amide and then dehydrating, general formula (IA-4), which includes general formula (Iai) from general formula (Iag), general formula (Iar) from general formula (Iap), general formula (Ibi) from general formula (Ibg) and general formula (Ibr) from general formula (Ibp):

29~
~ z2 z R-~- L
m M1 CN (IA-4) (wherein, R, L, Z2, Z3, Z9, ring A and m are the same as previously defined, M' represents a single bond or an alkenyl group having 1-4 carbon atoms, and the decahydronaphthalene ring has a trans form) can be produced.

1-5 Production of General Formula (Iau) from General Formula (Ias) and General Formula (Ibu) from General Formula (Ibs) After acid chloridation of general formula (XVIII):
R4-f{ A )--L
~ ~J m CO2H (XVIII) (wherein, R 4 represents an alkyl group, alkenyl group, alkoxy group or alkoxyalkyl group, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), obtained by reacting an oxidant such as silver oxide with general formula (XVII) obtained in the production process of general formula (XI) for which the production method has been already described:
R4--~~-L
~ ~/ m CHO (XVII) (wherein, R 4 represents an alkyl group, alkenyl group, alkoxy group or alkoxyalkyl group, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), by reacting with a compound of general formula (XIX):

HO Z (XIX) (wherein, Z is the same as previously described in general formula (I), and Z2, Z3 and Z4 are the same as previously defined), general formula (IA-5), which includes general formula (Iau) from general formula (Ias) and general formula 5 (Ibu) from general formula (Ibs):
/~' Z4 Z2 R4--K A~--L
\~--J K:t' C02 Z (IA-5) (wherein, R9, L, Z2, Z3, Z9, ring A and m are the same as previously defined, Z is the same as previously described in general formula (I), and the decahydronaphthalene ring has a trans form), can be produced.

10 1-6 Production from General Formula (Ici) from General Formula (Ica) and General Formula (Icu) from General Formula (Icm) General formula (IA-6), which includes general formula 15 (Ici) from general formula (Ica) and general formula (Icu) from general formula (Icm):

R4-~ A ~--L
m O O Z' (IA-6) (wherein, R4, L, Z1, Z2, Z3, Z9, ring A and m are the same as previously defined, Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form), can be produced by reacting general formula (III) with general formula (XIV), for which the production method has already been described, in the presence of transition metal catalyst.

1-7 Synthesis of General Formula (Idi) from General Formula (Ida) General formula (IA-7), which includes general formula (Idi) from general formula (Ida):

/ 21 Z2;K4 R4-A~L
\ \--~ m O O CN (IA-7) (wherein, R9, L, Z2, Z3, Z9, ring A and m are the same as previously defined, Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form), can be produced using the method described in 1-4 and a phenyldecahydronaphthalene derivative represented by general formula (IA-6a) for which the synthesis method has already been described:

~/'~~ ~ Z2Z4 ~
R4-{{ A }-L
O O (IA-6a) ~ ~/ I
DO

(wherein, R9, L, Z', Z2, Z3, Z9, ring A and m are the same as previously defined, Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form).

1-8 Production of General Formula (Idu) from General Formula (Idm) By converting general formula (XVIII), for which the production method has already been described, into an acid chloride followed by reacting with a compound of general formula (XX):

Ho O O z (XX) (wherein, Z, Z2, Z3, Z4 , ring A and m are the same as previously defined, and the plurality of Z2, Z3 and Z4 may be the same or different), general formula (IA-8), which includes general formula (Idu) from general formula (Idm):

/ Z4 z2z4 z2 R4-i~~q~---L
\~,~ C~Z a o z (IA_8) (wherein, R9, L, Z, Z2, Z3, Z9, ring A and m are the same as previously defined, the plurality of Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form) can be produced.

1-9 Production of General Formula (Ier) from General Formula (Iea) General formula (IA-9), which includes general formula (Icr) from general formula (Ica):

~~''\ Z ZZZ¾ Z2 R4-f( A }-L -\\-J (~ Q r (IA-9) z3 Z3 (wherein, R4, L, Z1, Z2, Z3, Z9, ring A and m are the same as previously defined, the plurality of Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form), can be produced by reacting general formula (XXI):

Z~ Z2 HC=C Z' (XXI) (wherein, Z1, Z2, Z3 and Z4 are the same as previously defined) with general formula (XIV), for which the production method has already been described, in the presence of transition metal catalyst.

1-10 Production of General Formula (Iff) from General Formula (Ifa), General Formula (Ifo) from General Formula (Ifj) and General Formula (Iry) from General Formula (Irm) After reacting an organometallic reagent (XXII):

W
X, 0 r (xxll) X"

(wherein, X1, X2, X3, X4 and X5 respectively and independently represent a hydrogen atom, fluorine atom or chlorine atom, and W and Z' are the same as previously defined) with a decahydronaphthalene derivative represented by general formula (IIa), by then dehydrating in the presence of acid catalyst, hydrogenating the double bond of the octahydronaphthalene ring, and isomerizing in the presence of alkaline catalyst as necessary, (IA-10), which includes general formula (Iff) from general formula (Ifa), general formula (Ifo) from general formula (Ifj) and general formula (Iry) from general formula (Irm) R2-i \l-J Kb)~
Z' (IA-10) X
3 Xz (wherein, R2, L, X1, X2, X3, X9, X5, Z1, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced.

1-11 Synthesis of General Formula (Ifi) from General Formula (Ifg) and General Formula (Ifr) from General Formula (Ifp) After demethoxyating general formula (XXIII), for which the synthesis method has already been described:

R2-}{ A }- L
m OCH3 (XXIII) (wherein, R2, L, X1, X2, X3, X4, X5, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) using hydrobromic acid and so forth to obtain phenol derivative (XXIV):

~~''~ X~
R2-F( A }- L
\ \_/ m O
OH (XXIV) X, (wherein, R2, L, X1, X2, X3, X9, X5, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), and converting to an elimination group by allowing p-toluene sulfonyl chloride or trifluoromethane sulfonic acid anhydride to act on this, by reacting with potassium cyanate and so forth in the presence of transition metal catalyst, general formula (IA-il), which includes 5 general formula (Ifi) from general formula (Ifg) and general formula (Ifr) from general formula (Ifp):

~/~~ X5 R~-{-\( A }- Lm k~O Xi ~J
O CN (IA-11) (wherein, R2, L, X1, X2, X3, X9, X5, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced. Here, a palladium complex or 10 nickel complex is preferable for the transition metal catalyst.

1-12 Synthesis of General Formula (Igp) from General Formula (Iga) After reducing decahydronaphthalene derivative (II) to 15 obtain alcohol derivative (XXV):

Rz-~ A ~--L
~ ~/ m pH (XXV) (wherein, R2, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), by either reacting this with a halogenating agent, p-toluene sulfonyl chloride or trifluoromethane sulfonic acid anhydride, 20 a compound represented by general formula (XXVI):

RZ-{-( A ~-- L \ ~/ K)C, (XXVI) (wherein, V represents a bromine or iodine halogen atom or an elimination group such as a p-toluene sulfonyloxy group or a trifluoromethane sulfonyloxy group, R2, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) is obtained. By then reacting this compound with a metal such as magnesium or alkyl lithium and so forth, organometallic reagent (XXVII):

R2-{{ A }- L
~ ~J m W (XXVII) (wherein, W, R2, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) is prepared, and after reacting this with 1,2,3,4-tetrahydronaphthalene-2-one derivative (XXVIII):
X
O O
Zi (XXVIII) X3 Xz (wherein, X1, X2, X3 and Z' are the same as previously defined), by dehydrating in the presence of acid catalyst to obtain 1,2-dihydronaphthalene derivative followed by hydrogenating the double bond of the 1,2-dihydronaphthalene ring, general formula (IA-12), which includes general formula (Igp) from general formula (Iga):

RZ-i~ H r- L X~
m Zl (IA-12) (wherein, R2, L, X', X2, X3, Z1, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced.

1-13 Synthesis of General Formula (Igt) from General Formula (Igq) General formula (IA-13), which includes general formula (Igt) from general formula (Igq):

R2-~-( A }- L
~~J
CN (IA-13) (wherein, R2, L, X1, X2, X3, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced by using the method described in 1-4 and a phenyldecahydronaphthalene derivative represented by general formula (IA-12a), for which the synthesis method has already been described:

R2-t( O (IA-12a) k k (wherein, Rz, L, X1, X2, X3, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form).

1-14 Synthesis of General Formula (Icl) from General Formula (Icj) and General Formula (Icx) from General Formula (Icv) After reacting organometallic reagent (XXVII) with formula (XXIX):

C(XXIX) by preparing general formula (XXX):
Rz-K /'~ )- L O
~~--/ OD (XXX) (wherein, R2, L, ring A and m are the same as previously defined, and the octahydronaphthalene ring has a trans form) by dehydrating in the presence of acid catalyst, hydrogenating the double bond and removing the protection of the carbonyl groups under acidic conditions, general formula (XXXI):

R2-{~( H }- L
~ ~1 O (XXXI) (wherein, R2, L, ring A and m are the same as previously defined, and the octahydronaphthalene ring has a trans form) is obtained. After reacting this with organometallic reagent (III), by dehydrating in the presence of acid catalyst, hydrogenating the double bond of the octahydronaphthalene ring and isomerizing in the presence of alkaline catalyst as necessary, (IA-14), which includes general formula (Icl) from general formula (Icj) and general formula (Icx) from general formula (Icv):

/~--~ Z Z2 R2-}( A }- L
~`-J O Z~ (IA-14) (wherein, R2, L, Z1, Z2, Z3, Z4 , ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) can be produced.

1-15 Synthesis of General Formula (Idl) from General Formula (Idj) General formula (IA-15), which includes general formula (Idl) from general formula (Idj):

~/~~ Z4 R2-K /~ }- L ~`--/ CN (IA-15) (wherein, R2, L, Zz, Z3, Z9, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced using the method described in 1-4 and a phenyldecahydronaphthalene derivative represented by general formula (IA-14a), for which the synthesis method has already been described:

R2-(I
A-14a) Zs (wherein,.R2, L, Z2, Z3, Z4 , ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form).

1-16 Synthesis of General Formula (Idx) from General Formula (Idv) With the exception of using for the raw material a phenol derivative that can be produced from general formula (XXXI) or general formula (IA-1), for which the synthesis methods have already been described, general formula (IA-16), which includes general formula (Idx) from general formula (Idv):

// Z'~ Z2 Rz- f{ A~-- L
t`--~ A CO Z (IA-16) (wherein, R2, L, Z2, Z3, Z4, Z, ring A and m are the same as previously defined, the plurality of A may be the same or different, and the decahydronaphthalene ring has a trans form) can be produced using the method described in 1-5.

5 2. Synthesis of General Formula (I) - 2 2-1 Synthesis of General Formula (Inj) from General Formula (Ina) After reacting Wittig's reagent (VIII) with general -__ formula (IIa), by hydrolyzing and isomerizing to the trans 10 form using base and then repeating reaction with (VIII) and hydrolysis, alkanal derivative (L):

Ra-{-( A }-L
~ \_/ m (CH2i-CHO (L) (wherein, 1 represents an integer of 0 or greater, R9, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) is obtained.

15 After reacting this with general formula (X), by isomerizing the double bond to the trans conformation by allowing benzene sulfinic acid to act on the product as necessary, (IB-1), which includes general formula (Inj) from general formula (Ina):

R4-~-L
~ L1 +n (CFhh_A_3 (IB-1) R

(wherein, 1 represents an integer of 0 or greater, R4, R3, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced.
In addition, after reducing alkanal derivative (XXIX) or general formula (IIa) to obtain an alcohol derivative and converting this to an alkoxide, by reacting with alkyl halide, a compound in which n = 0 and Z is an alkoxy group and so forth in general formula (I) can also be produced.

2-2 Synthesis of General Formula (Ino) from General Formula (Ink) (IB-2), which includes general formula (Inj) from general formula (Ina):

R4-~-( A }- L
~~J m (CHZh-% (IB-2) (wherein, R3, R9, L, ring A, 1 and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced in the same manner as 2-1 with the exception of using general formula (XXXI) as the raw material. In addition, after reducing the alkanal derivative or general formula (XXXI) to obtain an alcohol derivative and converting this to an alkoxide in the same manner as 2-1, by reacting with alkyl halide, a compound in which Z is an alkoxy group and so forth in general formula (I) can be produced.
Furthermore, an alkenyl form of general formula (XXXI) can also be produced according to 1-2.

2-3 Synthesis of General Formula (Iow) from General Formula (Ioa), General Formula (Ipe) from General Formula (Ipa) General Formula (Ipi) from General Formula (Ipg) and General Formula (Iqe) from General Formula (Igb) General Formula (XXXII):

~/~'\ Z4 Z2 R4-t( H j-r_ \ 1..~ M' (XXXII) (wherein, ring A, R4, m, n, L, Ml, Z 2, Z3 and Z4 are the same as previously defined, ring D represents a 1,4-phenylene group or trans-l,4-cyclohexylene group, and decahydronaphthalene ring have trans forms, which can be produced by the above methods or their combinations, can be obtained. An organometallic reagent is then produced that is prepared by directly iodinating or brominating this, or lithionating with alkyl lithium, and allowing the bromine or iodine to react, followed by reacting with a metal such as magnesium or transmetalating using an organometallic reagent such as alkyl lithium. By then allowing this to react with dimethylformamide (DNF), general formula (XXXIII) :

~/~\ Z^ Z?
R4-j{ H 1-L
~`.-/ D M' CHO (XXXIII) (wherein, ring A, ring D, R4, m, n, L, M1, Z2, Z3 and Z4 are the same as previously defined, and decahydronaphthalene ring have trans forms is produced. After allowing Wittig's reagent (VIII) to react with this, by hydrolyzing and isomerizing to the trans form using base, and then repeating reaction with (VIII) and hydrolysis, alkanal derivative (XXXIV):

R4--~1 A,--L
~~/ D M' (CH2)i- CHO (XXXIV) n Kb~

(wherein, ring A, ring D, R4, 1, m, n, L. Ml, Z2, Z3 and Z4 are the same as previously defined, and the decahydronaphthalene ring has a trans form) is obtained. After reacting general formula (X) with this, by isomerizing the double bond to the trans conformation by allowing benzene sulfinic acid to act on this as necessary, general formula (IB-3), which includes general formula (Iow) from general formula (Ioa), general formula (Ipe) from general formula (Ipa), general formula (Ipi) from general formula (Ipg) and general formula (Iqe) from general formula (Iqb) R4--~1 A,--L
~tJ KZ:)-&M1;~*(CH2)7-%- (IB-3) (wherein, ring A, ring D, R3, R4, 1, m, n, L. Ml, Z2, Z3 and Z4 are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced. In addition, after reducing alkanal derivative (XXXIV) to obtain an alcohol derivative and converting this to an alkoxide, by reacting with alkyl halide, a compound can also be produced in which R is an alkoxy group and so forth. Furthermore, the production method of a compound that does not contain an alkenyl group has been previously described.
2-4 Synthesis of General Formula (Ira) from General Formula (Ipf) General formula (IB-4), which includes general formula (Ipf) and general formula (Ira):

R2-K r+ r--L ~~! YD&G, M' (CHz h~ R3 (wherein, ring A, ring D, R3, R2, m, n, 1, L and M1 are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced by the same method as 2-1 using general formula (XXXV):

R2-t( /~ j- L
~ ~--J MO (XXXV) n (wherein, ring A, ring D, R2, L, m, n and M1 are the same as previously defined, and the decahydronaphthalene ring has a trans form which can be produced according to the method of 1-13 and 1-14.
2-5 Synthesis of General Formula (Ipt) from General Formula (Ipk) After reacting the following compound:

W R2 (XXXVI) (wherein, R2, Z2, Z3, Z4 and W are the same as previously defined) with general formula (VIIa) or general formula (VIIb), by dehydrating in the presence of acid catalyst, hydrogenating the double bond of general formula (XXXVIIa) or general formula (XXXVIIb):

~

RZ O O
R2 (XXXVia) Z2 ~ 24 Z2 R2 ~ L R2 (XXXVIb) (wherein, R2, Z2, Z3, Z4 and L are the same as previously defined, the plurality of R2, Z2, z 3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans form) and isomerizing in the presence of alkaline catalyst as 5 necessary, general formula-(IB-5), which includes general formula (Ipt) from general formula (Ipk):

Z2 Z4 .

m R2 (IB-5) (wherein, m, R2, Zz, Z3, Z9 and L are the same as previously defined, the plurality of R2, Z2, Z3 and Z4 may be the same or different, and the decahydronaphthalene ring has a trans 10 form), can be produced.

2-6 Production of General Formula (Iqi) from General Formula (Iqf) and General Formula (Iqt) from General Formula (Iqk) General formula (IB-6), which includes general formula 15 (Iqi) from general formula (Iqf) and general formula (Iqt) from general formula (Iqk):

Za Z2Z4 Z2 a R q L m O O R4 (IB-6) (wherein, Ra, L, Z2, Z3, Z4 , ring A and m are the same as previously defined, the plurality of Z2, Z3, Z4 and R4 may be the same or different, and the decahydronaphthalene ring has a trans form), can be produced by reacting general formula (XXXVI) with general formula (XIV), for which the production method has already been described, in the presence of a transition metal catalyst.
2-7 Synthesis of General Formula (Irf) from General Formula (Ira) After reacting organometallic reagent (XXVII) with general formula (IIa) or general formula (XXVIII), by dehydrating in the presence of acid catalyst and then hydrogenating the double bond, general formula (IB-7), which includes general formula (Igp) from general formula (Iga):

R2~L q L-{ A }~-R2 (IB-7) m ~--~ ~

(wherein, R2, L, Z2, Z3, Z4, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form), can be produced.
2-8 Synthesis of General Formula (Irk) from General Formula (Irg) After reacting the following compound:

z, z2 W R2 (XXXVI) z3 (wherein, R2, Z2, Z3, Z4 and W are the same as previously defined) with general formula (XXXI), by dehydrating in the presence of acid catalyst, hydrogenating the double bond of general formula (XXXIX):

R2- F+ L
\~J m R2 (XXXIX) k4 (wherein, ring A, m, n, L, X 4 and X5 are the same as previously defined, the plurality of R2 may be the same or different, and the decahydronaphthalene ring has a trans form), and isomerizing in the presence of alkaline catalyst as necessary, general formula (IB-8), which includes general formula (Irk) from general formula (Irg):

~~~
R2-K ~"~ }- L

`~J n Rz (I B-8) X, (wherein, ring A, m, n, L, X4 and X5 are the same as previously defined, the plurality of R2 may be the same or different, and the decahydronaphthalene ring has a trans form), can be produced.

3. Synthesis of General Formula (I) - 3 3-1 By reacting a phenyl lithium reagent represented by general formula (XVa) :

Z, Z2 R4-~- L
m M' Li (XVa) (wherein, R4, L, Z2, Z3, Z9, ring A, M1 and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) with a phenyltrifluoroethylene derivative represented by general formula (XL):

CF2=CF Z (XL) (wherein, Z1, Z2, Z3 and Z 4 are the same as previously defined) and de-protecting the protective groups--as necessary, general formula (IC-Z) :

//~\ Z4 Z2 Z4 Z2 R4-}{ A }-L
\~--J m M~ CF=CF Z' (IC-1) (wherein, R9, L, Z1, Z2, Z3, Z9, ring A, M1 and m are the same as previously defined, the plurality of Z2, Z3 and Z4 may be the same or different, the steric form of the double bonds represents the trans form, and the decahydronaphthalene ring has a trans form) can be produced.

3-2 By reacting a thiocarboxylate-O-ester represented by general formula (XLI):

R2--~~A }--L O O Z (XLI) ~~J

(wherein, R2, L, ) Z2, Z3, Z9, ring A and m are the same as previously defined, the plurality of rings A may be the same or different, and the decahydronaphthalene ring has a trans form) with a fluorinating agent such as DAST, and de-protecting the protective groups as necessary, general formula (IC-2):

Za Z2 R2-~~ A~-- L O Z(i C-2) Kb-(D--(wherein, R2, L, Z2, Z3, Z9, Z, ring A and m are the same as previously defined, the plurality of rings A may be the same or different, and the decahydronaphthalene ring has a trans form) can be produced.

Here, thiocarboxylate-O-ester can be produced by reacting the corresponding carboxylate ester (IA-16) with Lawesson's reagent.

3-3 General formula (IC-3):
R4-~ ( A )-L
\ ~J (CH2)1-CF2H (IC-3) (wherein, 1 is an integer of 0 or greater, R9, L, ring A and m are the same as previously defined, and the decahydronaphthalene ring has a trans form) can be produced by reacting sodium chlorodifluoroacetate with an alkanal derivative (L) to overheating.

4. Synthesis of General Formula (I) Intermediates 4-1 Synthesis of General Formula (II) After reacting general formula (XLIII):

Br Cb OCH3 (XLIII) with general formula (XLIV):
R4~O/mW (XLIV) (wherein, R4, W and m are the same as previously defined) in the presence of a transition metal catalyst, by de-protecting the resulting general formula (XLV):

C-OCH3 (XLV) 5 (wherein, R 4 and m are the same as previously defined), general formula (XLVI):

R4-( O OH (XLVI) (wherein, R9,01W and m are the same as previously defined) is obtained. By then hydrogenating the aromatic rings of this compound, general formula (XLVII):

K)~ O (XLVII) 0 (wherein, R2 and m are the same as previously defined) can be produced. In addition, after reacting general formula (XLVIII):

R40 (XLVIII) (NL~eve~r~; ~~yJJ-S 4-1vc ---~ccv-rC',cf-i, with general formula (XLIIIa):
Wa O OCH3 (XLllla) (wherein, W is the same as previously defined) and dehydrating, general formula (XLIX):
R4 ~C% OCH3 (XLIX) (wherein, R4 and m are the same as previously defined) is obtained. General formula (XLVII) can also be produced by hydrogenating this compound.

4-2 Synthesis of General Formula (V-1) Formula (V-1D) is obtained by hydrogenating formula (V-iC). General formula (V-1) Ul -Cz~>= UZ (V-1) (wherein, U1 and U2 are the same as previously defined) can be produced by acetalation of the carbonyl groups followed by isolation of the diketone, monoacetal and diacetal.
4-3 Synthesis of General Formula (V-2) General formula (LII):
O
(CH2)k ~O O OH (LII) (wherein, k is the same as previously defined) is obtained by reacting general formula (XLIV) with general formula (V-lA), dehydrating, de-protecting the resulting compound and reacetalization. General formula (V-2) in which L is a single bond can then be produced by hydrogenating the aromatic ring of this compound and oxidizing or acetalating as necessary.

In addition, general formula (LI):

O
(CH2)k `O OH (LI) (wherein, k is the same as previously defined) is obtained by reacting general formula (XLIIIa) with general formula (V-lA), dehydrating, de-protecting the resulting compound and reacetalization. General formula (V-2) in which L is a single bond can then be produced by hydrogenating the aromatic rings of this compound and oxidizing or acetalating as necessary.
Furthermore, in cases when L is not a single bond, general formula (LIII) or general formula (LIV):

O
(CH2)k ~ ~! L O
`O OH (LIII) O
(CH2)k /~~
O L--(( )}-OH (LIV) qr~C+ t' a~ E- \~/
(wherein, kJ~9j the same as previously defined) is obtained in 0 accordance with the method described above. This compound can be obtained by hydrogenating using the method described above.

Specific examples of typical examples of compound (I) of the present invention produced in this manner are summarized in Table 1.

Table 1 Compound 1 Represented by General Formula (I):
R-~~q }-L ~--~
~ ~J M-( R }~.. Z ( I ) Compound Formula Phase transition temperature ( C) I-1 n-C3H7 F C 52 (N 46) I
F
1-2 n-C3H7 -0 F o i l F
1-3 n~h O F C 46 I
F

1-4 n-r,H' OOCF3 C 47 I
F

F

F

F
1-8 n-w-y O F -F

(In the table, C indicates the crystal phase, N the nematic phase, and I an isotropic liquid.) Table 2 Compound 2 Represented by General Formula (I) L
R-~- -r-~~-l -vl-( ~ l f- Z t ~) Phase transition Compound Formula temperature ( C) F
1-9 n-CA O -CN

F
I-10 n-C3~h O cN C 86 (N 18) I
F
F
I-11 Q cN C 80 N 129 I

F
F
1-12 Q cN C 88 I

F

F
1-13 c02 4CN -F
F
1-14 ~ (:sHõ& /~( -coz-~r' CN

F
1-15 rO- cN -(In the table, C indicates the crystal phase, N the nematic phase, and I an isotropic liquid.) Table 3 Compound 3 Represented by General Formula (I):
RffA,--L

Compound Formula Phase transition temperature ( C) F
1-17 n-cA C 62 N 188 I
F
F
n-C3H7 F

1-19 "-CA O oGF3 C 94 N 215 I
F
n-C5Hjj 1-20 O ~ F -F
F F
n-C3Fi7 F

(In the table, C indicates the crystal phase, N the nematic phase, and I an isotropic liquid.) Table 4 Compound 4 Represented by General Formula (I) R-Vq, -L /
\`-J
`~~ M-< B )+Z (I) l_J ~n Phase transition Compound Formula temperature ( C) 1-22 oil I-24 nc3H7 C 67 N 139 I
1-25 F n-C~H, C 30 N 99 I
F
I-26 n-C31+i -1-27 nc3-ti O F
-O F

n-Cyli~

-(In the table, C indicates the crystal phase, N the nematic phase, and I an isotropic liquid.) Since many of the compounds represented by general formula (I) exhibit superior co-solubility with other liquid crystal materials, they can be suitably used as materials for liquid crystal display cells in the state of a mixture with other liquid crystal compounds. Although the compound of (I) can be used in any of the various display methods previously described, they are suited for use in simple matrix driving or active matrix driving TN display elements and STN display elements.

In this manner, although compositions provided by the present invention contain at least one type of compound represented by general formula -(I) as their first component for as preferable typical examples of nematic liquid crystal compounds that can be used by mixing with a compound represented by general formula (I), they particularly preferably contain at least one type of the second to fourth components indicated below as other components.

Namely, the second component is a so-called fluorine-based (halogen-based) p type liquid crystal compound that is composed of the compounds indicated in general formulas (Al) through (A3) below.

Rb--( A }-Le--( Z }-Pe (Al) Rb--&La'--&Lb--t [. J-Pa (A2) Re--{ A t-L -&Lb--( C}-L`-( Z r-P8 (A3) In the above formulas, -R--b represents an alkyl group having 1-12 carbon atoms, these may have a straight chain or methyl or ethyl branched structure, a 3-6 membered ring structure, any arbitrary -CH2- present in the group may be replaced by -0-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF- or -C = C-, and any arbitrary hydrogen atom present in the group may be substituted with a fluorine atom or trifluoromethoxy group.
However, a straight chain alkyl group having 2-7 carbon atoms, straight chain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenyl group having 4-7 carbon atoms and an alkyl group having 1-5 carbon atoms in which the terminal is substituted with an alkoxyl group having 1-3 carbon atoms are preferable. In addition, the compound may have optical activity or be a racemic mixture in the case asymmetric carbons are formed as a result of branching.

Rings A, B and C respectively and independently represent a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene group that may be substituted with one or more fluorine atoms, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group. However, a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with a fluorine atom, or 1,4-phenylene group that may be substituted with 1 or 2 fluorine atoms is preferable. In particular, it is preferable that ring A be a trans-1,4-cyclohexylene group in the case ring B is a trans-1,4-cyclohexylene group or trans-decahydronaphthalene-trans-2,6-diyl group, and it is preferable that rings B and A be trans-1,4-cyclohexylene groups in the case ring C is a trans-1,4-cyclohexylene group or trans-decahydronaphthalene-trans-2,6-diyl group. In addition, it is preferable that ring A be a trans-1,4-cyclohexylene group in (A3).

La, Lb and L` are connecting groups that respectively and independently represent a single bond, ethylene group ( -CHZCHZ- ) , 1, 2 -propylene group ( -CH ( CH3 ) CHZ- and -CH2CH ( CH3 ) - ) , 1,4-butylene group, -COO-, -OCO-, -OCF2-, -CF2O-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF-, -C = C- or -CH=NN=CH-. However, a single bond, ethylene group, 1,4-butylene group, -COO-, -OCF2-, -CFzO-, -CH=CF- or -C C- is preferable, and a single bond or ethylene group is particularly preferable. In addition, it is preferable that at least one of these represent a single bond in (A2), and at least two of these represent a single bond in (A3).

Ring Z is an aromatic ring that can be represented by general formulas (La) through (Lc) below.

Y Ya Y9 Yf Yd Yh Y (La) (Lb) (Lc) b o 0 Ye Y' In these formulas, ya through Y5 respectively and independently represent a hydrogen atom or fluorine atom.
However, it is preferable that at least one of Ya and Yb be a fluorine atom in (La), and it is preferable that at least one of y d through Yf be a fluorine atom in (Lb), with Yd particularly 5 preferably being a fluorine atom.
Terminal group Pa represents a fluorine atom, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group or difluoromethyl group, or an alkoxyl group, alkyl group, alkenyl group or alkenyloxy group having 2 or 3 carbon 10 atoms that is replaced by a fluorine atom or more than one fluorine atoms. However, a fluorine atom, trifluoromethoxy group or difluoromethoxy group is preferable, and a fluorine atoms is particularly preferable.
In addition, the compounds of general formula (I) of the 15 present invention are excluded in (A2).
The third component is a so-called cyano-based p type liquid crystal compound, and is composed of the compounds indicated with general formulas (Bl) through (B3) below.
R`--{ D rL"---( Y }-Pb (B1) R -( D}--L --( E}-Le--( Y r-Pb (B2) R`.--( D)-Ld-_E 1-Le-{ F}-Lf-_Y}-pb (B3) ~J \_/ ~_/ ~/
In the above formulas, Rc represents an alkyl group having 1-12 carbon atoms, and these may have a straight chain or methyl or ethyl branched structure, a 3-6 membered ring structure, any arbitrary -CH2- present in the group may be replaced by -0-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF- or -C = C-, and any arbitrary hydrogen atom present in the group may be substituted with a fluorine atom or trifluoromethoxy group.
However, a straight chain alkyl group having 2-7 carbon atoms, straight chain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenyl group having 4-7 carbon atoms and an alkyl group having 1-5 carbon atoms in which the terminal is substituted with an alkoxyl group having 1-3 carbon atoms are preferable. In addition, the compound may have optical activity or be a racemic mixture in the case asymmetric carbons are formed as a result of branching.

Rings D, E and F respectively and independently represent a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene group that may be substituted with one or more fluorine atoms, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group. However, a trans-l,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with a fluorine atom, or 1,4-phenylene group that may be substituted with 1 or 2 fluorine atoms is preferable. In particular, it is preferable that ring D be a trans-l,4-cyclohexylene group in the case ring E is a trans-1,4-cyclohexylene group or trans-decahydronaphthalene-trans-2,6-diyl group, and it is preferable that rings D and E be trans-1,4-cyclohexylene groups in the case ring F is a trans-l,4-cyclohexylene group or trans-decahydronaphthalene-trans-2,6-diyl group. In addition, it is preferable that ring D be a trans-1,4-cyclohexylene group in (B3).

Ld, Le and Lf are connecting groups that respectively and independently represent a single bond, ethylene group ( -CH2CH2- ) , 1, 2 -propylene group ( -CH ( CH3 ) CH2- and -CH2CH ( CH3 ) - ) , l0 1,4-butylene group, -COO-, -OCO-, -OCF2-, -CF20-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF-, -C=C-, -OCH2-, -CH2O- or -CH=NN=CH-. However, a single bond, ethylene group, -COO-, -OCF2-, -CF2O-, -CF=CF- or -C = C- is preferable, and a single bond, ethylene group or -COO- is particularly preferable. In addition, it is preferable that at least one of these represent a single bond in (B2), and at least two of these represent a single bond in (B3).

Ring Y is an aromatic ring that can be represented by general formulas (Ld) through (Lf) below.

yk Y
m (Ld) O Y (Le) Y (Lfl Y, O ~
" YQ
In these formulas, Yk through yq respectively and independently represent a hydrogen atom or fluorine atom. However, Yn and.Y
are preferably hydrogen atoms in (Le). Although terminal group pb represents a cyano group (-CN-), cyanato group (-OCN-) or -C = CCN, a cyano group is preferable.

In addition, the compounds of general formula (I) of the present invention are excluded in (B2).

The fourth component is a non-polar liquid crystal having dielectric anisotropy of near 0, and is composed of the compounds indicated with general formulas (Cl) through (C3) below.

Rd-( G }-L9-{ H }-PQ (Cl) R -G-Lg--&L^--&Pe (C2) Rd--( DrLa-{ H?-L"--j I?--L'-~( J)--P (C3) In the above formulas, Rd and pe respectively and independently represent an alkyl group having 1-12 carbon atoms, and these may have a straight chain or methyl or ethyl branched structure, a 3-6 membered ring structure, any arbitrary -CH2- present in the group may be replaced by -0-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF- or -C=C-, and any arbitrary hydrogen atom present in the group may be substituted with a fluorine atom or trifluoromethoxy group.
However, a straight chain alkyl group having 1-7 carbon atoms, straight chain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenyl group having 4-7 carbon atoms and an alkyl group having 1-5 carbon atoms in which the terminal is substituted with an alkoxyl group having 1-3 carbon atoms are preferable. Moreover, it is more preferable that at least one of these represent a straight chain alkyl group having 1-7 carbon atoms, a straight chain 1-alkenyl group having 2-7 carbon atoms, or a straight chain 3-alkenyl group having 4-7 carbon atoms.

Rings G, H, I and J respectively and independently represent a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene group that may be substituted with one or two fluorine atoms, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with one or two fluorine atoms, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group. However, it is preferable that in each compound there be no more than one trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and that the other rings be a trans-1,4-cyclohexylene group or a 1,4-phenylene group that may be substituted with 1 or 2 fluorine atoms or methyl groups.
L9, Lh and L' are connecting groups that respectively and independently represent a single bond, ethylene group ( -CH2CH2- ) , 1, 2 -propyl ene group ( -CH ( CH3 ) CH2- and -CH2CH ( CH3 ) -) , 1,4-butylene group, -COO-, -OCO-, -OCF2-, -CF20-, -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF-, -C = C- or -CH=NN=CH-. However, a single bond, ethylene group, -COO-, -OCF2-, -CF2O-, -CF=CF- or -C = C- is preferable, and a single bond, ethylene group, 1,4-5 butylene group, -COO-, -OCO-, -OCF2-, -CFZO-, -CF=CF-, -C=
C- or -CH=NN=CH- is particularly preferable. In addition, it is preferable that at least one of these represent a single bond in (C2), and at least two of these represent a single bond in (C3).

10 In addition, the compounds of general formula (I) of the present invention are excluded in (C2).

More preferable forms in (Cl) can be represented by general formulas (Cla) through (Clh) below.

O H2 R9 (C1b) Rf G1 H1 Rg (C1a) Rf G2 R' G2 = H2 Rg (C1c) H2 R9 (C1d) Rf G2 F
H2 Rg (Cle) O H2 Rg (Cl~
R' G2 Rf G2 F FF
R' G2 H2 R9 (C19) Rf G3 N H3 Rs (C1h) In each of the above formulas, Rf and Pg respectively and 15 independently represent a straight chain alkyl group having 1-7 carbon atoms, straight chain 1-alkenyl group having 2-7 carbon atoms, straight chain 3-alkenyl group having 4-7 carbon atoms, straight chain alkoxyl group having 1-3 carbon atoms or a straight chain alkyl group having 1-5 carbon atoms in which the terminal is substituted with an alkoxyl group having 1-3 carbon atoms. However, at least one of these represents a straight chain alkyl group having 1-7 carbon atoms, straight chain 1-alkenyl group having 2-7 carbon atoms or straight chain 3-alkenyl group having 4-7 carbon atoms. However, in the case rings G1 through G3 are aromatic rings, the case of the corresponding Rf being a 1-alkenyl group or alkoxyl group is excluded, and in the case rings H1 through H3 are aromatic rings, the case of the corresponding R9 being a 1-alkenyl group or alkoxyl group is excluded.

Rings G1 and Hi respectively and independently represent a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene group that may be substituted with one or two fluorine atoms, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with one or two fluorine atoms, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group. However, it is preferable that in each compound there be no more than one trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and that the other rings in this case be a trans-l,4-cyclohexylene group or a 1,4-phenylene group that may be substituted with 1 or 2 fluorine atoms or methyl groups. Rings G2 and H2 respectively and independently represent a trans-1,4-cyclohexylene group, trans-decahydronaphthalene-trans-2,6-diyl group, 1,4-phenylene group that may be substituted with one or two fluorine atoms or methyl groups, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, or tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms. However, it is preferable that in each compound there be no more than one trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms or tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, and that the other rings in this case be a trans-1,4-cyclohexylene group or a 1,4-phenylene group that may be substituted with one or two fluorine atoms or methyl groups. Rings G3 and H3 respectively and independently represent a 1,4-phenylene group that may be substituted with one or two fluorine atoms or methyl groups, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms or tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms.

However, it is preferable that in each compound there be no more than one naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms or tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms.

More preferable forms in (C2) can be represented by general formulas (C2a) through (C2m) below.

Rf G1 H1 11 R9 (C2a) R' G3 O !2 Rs (C2h) O
12 Re (C2b) O
R{ G2 H2 Rf G2 O 12 R9 (C2i) O
12 R9 (C2c) O O
R~ G2 H2 Rf G2 12 R9 (C2j) O p H2 O

R~ G2 H2 = 12 R9 (C2d) Rr G2 O O IZ R9 (C2k) O O
R' G2 H2 12 R9 (C2e) Ri G2 H3 13 Rg (C21) 13 R9 (C2t) R' G3 H3 F F O 12 Rg (C2m) 13 R9 (C2g) Rf G3 = H3 Rf G3 H3 O O

In the above formulas, rings G1, G2, G3, H1, H2 and H3 are the same as previously defined, and ring I1 is the same as ring G1, ring 12 is the same as ring G2 and ring 13 is the same as ring G3. In addition, it is preferable that in each compound there be no more than one trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and that the other rings in this case be a trans-1,4-cyclohexylene group or a 1,4-phenylene group that may be substituted with one or two fluorine atoms or methyl groups.

Next, more preferable forms in (C3) can be represented by general formulas (C3a) through (C3f) below.

R' G1 H1 11 J1 R9 (C3a) J2 R9 (C3b) Re G2 H2 12 J2 R9 (C3c) Rf G2 H2 IZ
O
O
J2 R9 (C3d) R' G2 H2 12 o 12 J2 Rg (C3e) Rf G H2 R' G2 H2 J2 R (C3f) In the above formulas, rings G1, G2, H1, H2, I1 and 12 are the same as previously defined, and ring J1 is the same as ring Gi or ring J2 is the same as ring G2. In addition, it is preferable that in each compound there be no more than one trans-decahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group that may be substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group that may be substituted with one or two fluorine atoms, 1,4-cyclohexenylene group that may be substituted with a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, and that the other rings in this case be a trans-1,4-cyclohexylene group or a 1,4-phenylene group that may be substituted with one or two fluorine atoms or methyl groups.
Examples The present invention will be further described with 5 reference to examples of the present invention shown below.
However, the present invention is not limited to these examples.

Example 1: Synthesis of trans-6-propyl-trans-2-(3,4,5-10 trifluorophenyl)-trans-decahydronaphthalene F
BrM ~ F

Pr F p"Ts0 i Pr 14F
O F
H2, Pd/C t-BuOK Pr -~ -~' F
F
3.6 g of magnesium was suspended in 3.5 ml of tetrahydrofuran (THF), and a 110 ml THF solution of 25.8 g of 1-bromo-3,4,5-trifluorobenzene was added dropwise to the suspension over a period of about 30 minutes at such a rate 15 that the THF was moderately refluxed. After further stirring the mixture for 1 hour, a 6 ml THF solution of 20 g of 6-propyl-trans-decahydro-2-naphthalenone, which was obtained according to the above reference example, was added dropwise over a period of 30 minutes. After further stirring the 20 mixture for 2 hours, 50 ml of 10% hydrochloric acid was added.
100 ml of hexane was added, and the organic phase was separated. The aqueous phase was extracted with 100 ml of hexane, and the extracts were combined with the organic phase.
The combined organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and 100 ml of toluene and 2.0 g of p-toluenesulfonic acid monohydrate were added. The mixture was heated at 110 C with stirring while evaporated water was separated and removed. When the evaporation of water was stopped, the temperature was reduced to room temperature. 50 ml of water was added, and the organic phase was separated.
The organic phase was rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the whole amount of the residue was dissolved in 200 ml of ethyl acetate. 2.5 g of palladium-carbon (5%, wet) was added, and the mixture was stirred in an autoclave in hydrogen under a pressure of 400 KPa. After stirring for 5 hours at room temperature, the catalyst was removed by way of filtration through celite; and the solvent was evaporated to obtain a trans/cis mixture of trans-6-propyl-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.
The whole amount of this mixture was dissolved in 55 ml of N,N-dimethylformamide (DMF). 1 g of potassium t-butoxide was added to the solution, and the mixture was stirred for 5 hours at 70 C. After the mixture was cooled to room temperature, 100 ml of water was added, and extraction was performed twice using 100 ml of hexane. Organic phases were combined, and the combined organic phase was rinsed with a diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane), and recrystallized twice from ethanol to obtain 5 g white crystals of trans-6-propyl-trans-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.

IR (neat) 1615, 1530cm- 1 1H NMR(Acetone-d6)87.4-6.8(m,2H),2.5-2.8(m,4H),1.9-0.7(m,18H) 13C NMR (Acetone-d6 ) cS154, 150, 140, 137, 146, 112, 43-34, 21, 15 MS m/z 310,267,247,225,211,197,185,171,158,145,135,123,109,95,81,67,5 The following compounds were prepared in the same manner as mentioned above:

trans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(4-fluorophenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3,4-difluorophenyl)-trans-decahydronaphthalene, trans- 6-propyl-trans-2- (4-trifluoromethoxyphenyl) -trans-decahydronaphthalene, trans-6-propyl-trans-2-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(4-chlorophenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3-fluoro-4-chlorophenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2 -(4-methoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene, trans-6-propyl-trans-2-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene.

Example 2: Synthesis of 6-(trans-4-propylcyclohexyl)-decahydro-2-naphthalenone (2-a) Synthesis of 6-(trans-4-propylcyclohexyl)-4,4a,5,6,7,8-hexahydro-3H-2-naphthalenone Oll n-C3H7 O n-C3H7 -C)-& N
CI
n-C3H Li 410 n"CA
O NHA) O

200 g of 4-(trans-4-propylcyclohexyl)cyclohexanone and 135.2 g of pyrrolidine were dissolved in 800 ml of toluene.
The solution was heated and stirred for 6 hours while water which is evaporated by azeotropic distillation was removed.
Azeotropic distillation of the solution was carried out with toluene so that excessive pyrrolidine was removed, and 1-(4-(trans-4-propylcyclohexyl)-cyclohexen-l-yl)-pyrrolidine was obtained. The product as it was was cooled to room temperature, and 800 ml of toluene was added again. The mixture was cooled in a water bath, and 150 ml toluene solution of 89 ml of methyl vinyl ketone was added dropwise over a period of 2 hours at 20 C or less. After the dropwise addition was completed, the temperature was increased over a period of 2 hours to reach the reflux temperature. The solution was cooled to room temperature, and a buffer solution of pH 5 which was prepared from 85.2 g of sodium acetate, 104.2 ml of acetic acid, and 104.2 ml of water was added.
Reflux was further continued for 5 hours. After the solution was cooled to room temperature, the organic phase was separated and rinsed with water and a saturated saline solution. The organic phase was dried on anhydrous sodium sulfate. The solvent was evaporated, and 313 g of 6-(trans-4-propylcyclohexyl) -4, 4a, 5, 6, 7, 8-hexahydro-2 (3H) -naphthalenone was obtained.

(2-b) Synthesis of 6-(trans-4-propylcyclohexyl)-octahydro-2-naphthalenone 21.8 g of metal lithium was added to 1500 ml of liquid ammonia which is cooled to -40 C. To the mixture, a 1200 ml 10 THF solution of 313 g of 6-(trans-4-propylcyclohexyl)-4, 4 a, 5, 6, 7, 8 -hexahydro- 2 (3H) -naphtha lenone which was obtained in (1-a) and 91 g of t-butanol were added dropwise at -35 C.
Stirring was carried out for 30 minutes, and 50 g of ammonium chloride was added to stop the reaction. The temperature was 15 gradually raised to evaporate ammonia. 200 ml of saturated aqueous solution of ammonium chloride and 400 ml of toluene were added. The organic phase was separated and rinsed with water and a saturated saline solution. The organic phase was dried on anhydrous sodium sulfate. The solvent was 20 evaporated, and distillation was carried out (bp.=180 C, 0.03 Ps) to obtain 96 g of 6-(trans-4-propylcyclohexyl)-octahydro-2-naphthalenone.

IR(nujol)1718cm-1 25 'H NMR(CDC13)02.4-2.2(m,4H),1.8-1.6(m,5H),1.4-1.0(m,20H),0.9(t,3H) 13C NMR(CDC13)0212,48,44,42,40,38,37,35,34,30,29,20,14 MS m/z 276, 258, 232, 152, 135, 125, 110, 95, 83, 69, 55 The following compounds were prepared in the same manner as mentioned above:

6-(trans-4-methylcyclohexyl)-octahydro-2-naphthalenone, 6-(trans-4-ethylcyclohexyl)-octahydro-2-naphthalenone, 6-(trans-4-butylcyclohexyl)-octahydro-2-naphthalenone, 6-(trans-4-pentylcyclohexyl)-octahydro-2-naphthalenone, 6-(trans-4-hexylcyclohexyl)-octahydro-2-naphthalenone, 6-(trans-4-heptylcyclohexyl)-octahydro-2-naphthalenone.
Example 3: Synthesis of trans-6-(trans-4-propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene F
n-C3H7 + BrMg O F
-0-0& O
F
F H2, Pd/C t-BuOK
n-C3H~
F DMF
F

n-C3H
F
F

2.1 g of magnesium was suspended in 4 ml of THF, and a 65 ml THF solution of 16.8 g of 1-bromo-3,4,5-trifluorobenzene was added dropwise to the suspension over a period of about 30 minutes at such a rate that the THF was moderately refluxed.
After further stirring the mixture for 1 hour, an 80 ml THF

solution of 20 g of 6-(trans-4-propylcyclohexyl)-octahydro- 2-naphthalenone, which was obtained Example 1, was added dropwise for 30 minutes. After further stirring the mixture for 2 hours, 50 ml of 10% hydrochloric acid was added. 100 ml of hexane was added, and the organic phase was separated. The aqueous phase was extracted with 100 ml of hexane, and the extracts were combined with the organic phase. The combined organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and 100 ml of toluene and 2.0 g of p-toluenesulfonic acid monohydrate were--added.- The mixture was heated at 110 C with stirring while evaporated water was separated and removed. When the evaporation of water was stopped, the temperature was reduced to room temperature. 50 ml of water was added, and the organic phase was separated.
The organic phase was rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the whole amount of the residue was dissolved in 200 ml of ethyl acetate. 2.5 g of palladium-carbon (5%, wet) was added, and the mixture was stirred in an autoclave in hydrogen under a pressure of 400 KPa. After stirring for 5 hours at room temperature, the catalyst was removed by way of filtration through celite, and the solvent was evaporated to obtain a trans/cis mixture of 6-(trans-4 -propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-.78 decahydronaphthalene. The whole amount of this mixture was dissolved in 55 ml of N,N-dimethylformamide (DMF). 0.7 g of potassium t-butoxide was added to the solution, and the mixture was stirred for 2 hours at 50 C. After the mixture was cooled to room temperature, 100 ml of water was added, and extraction was performed twice using 100 ml of hexane.

Organic phases were combined, and the combined organic phase was rinsed with a diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane), and recrystallized twice from ethanol to obtain 7.2 g white crystals of trans-6-(trans-4-propylcyclohexyl)-2-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene.
IR(nujol) 1615, 1533cm-1 1H NMR(CDC13)07.4-6.8(m,2H),2.5-2.8(m,4H),1.9-0.7(m,28H) 1 3 C NMR (CDC13) 2153, 149, 139, 136, 144, 110, 43-34, 20, 14 MS m/z 392,267,197,185,171,158,145,125,108,95,83,69,55 The following compounds were prepared in the same manner as mentioned above:

trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-fluorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,4-difluorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-chlorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-chiorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(4-methoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene, trans-6-(trans-4-propylcyclohexyl)-trans-2-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene.

Example 4: Synthesis of trans-6-(3,5-difluorophenyl)-trans -decahydronaphthalene-2-carbaldehyde F F
O 1) Ph3P-CHOCH3 OHC
=Cb 2) HCI bo 3) NaOH
F F
13.5 g of inethoxymethyltriphenylphosphonium chloride was suspended in 35 ml of THF. While the suspension was cooled to 5 10 C or lower, a 25 ml THF solution of 5.5 g of potassium t-butoxide was added dropwise. While the cooling was further continued, 25 ml THF solution of 8.5 g of 6-(3,5-difluorophenyl)decahydronaphthalen-2-one was added dropwise over a period of 10 minutes. After the temperature was 10 reduced to room temperature and stirring was carried out for 4 hours, water and hexane were added. The organic phase was separated, and rinsed with water. Then, the solvent was evaporated. 10.1 g of the solid substance obtained was dissolved in 50 ml of THF. 50 ml of 10% hydrochloric acid was 15 added, and the mixture was heated under refluxing for 2 hours.
The temperature was reduced to room temperature. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, and the combined organic phase was rinsed with saturated saline 20 solution. The solvent was then evaporated. 10 g of the oily substance obtained was dissolved in 100 ml of methanol. To the solution, which was cooled to 10 C or lower, 10 ml of 10%
aqueous solution of sodium hydroxide was added. After stirring for 2 hours, the temperature was reduced to room temperature. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic phase was rinsed with a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and 10.5 g of trans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde as an oily substance was obtained.

The following compounds were prepared in the same manner as mentioned above:

trans-6-(4-fluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3-fluoro-4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(4-methoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde, trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene-L0 2-carbaldehyde, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-decahydronaphthalene-2-carbaldehyde.
Example 5: trans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene F
OHC 1) Ph3P=CHOCH3 1) PIr3P=CHOCH3 O F2) HCI 2) HCI )P
F
OHC-(CNZ) O
F

13.5 g of inethoxymethyltriphenylphosphonium chloride was suspended in 35 ml of THF. While the suspension was cooled to 10 C or lower, a 25 ml THF solution of 5.5 g of potassium t-butoxide was added dropwise. While the cooling was further continued, 25 ml THF solution of 10.0 g of trans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in a manner similar to that of Example 1, was added dropwise. After the temperature was reduced to room temperature and stirring was carried out for 4 hours, water and hexane were added. The organic phase was separated, and rinsed with water. Then, the solvent was evaporated. 12.0 g of the solid substance obtained was dissolved in 60 ml of TH F.

60 ml of 10% hydrochloric acid was further added, and the mixture was heated under refluxing for 2 hours. The temperature was reduced to room temperature. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, and the combined organic phase was rinsed with saturated saline solution. The solvent was then evaporated. 11.0 g of trans-6-(3,4-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde obtained was dissolved in 40 ml of THF. The solution was added again dropwise to a 60 ml THF solution of 13.5 g of methoxymethyltriphenylphosphonium chloride and 5.5 g of potassium t-butoxide, which has been cooled. The temperature was reduced to room temperature. After the mixture was stirred for 4 hours, water and hexane were added, and the organic phase was separated. After the organic phase was rinsed with water, the solvent was evaporated. 13.6 g of the solid substance obtained was dissolved in 70 ml of THF. 70 ml of 10% hydrochloric acid was added to the solution, and the mixture was stirred for 2 hours. The temperature was reduced to room temperature, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic phase was rinsed with a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and 12.0 g of trans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene as an oily substance was obtained.

The following compounds were prepared in the same manner as mentioned above:

trans-6-(3,5-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, LO trans-6-(3,4,5-trifluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, 5 trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(2-formylethyl)decahydronaphthalene.

10 Example 6: Synthesis of trans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene F F
OHC
-lb PFr3P=CH2 CH2=CH
0.
F F

24.4 g of methyltriphenylphosphonium iodide was suspended in 75 ml of THF. While the suspension was cooled to 10 C or lower, a 40 ml THF solution of 7.6 g of potassium t-butoxide 15 was added dropwise. While the cooling was further continued, 100 ml THF solution of 20.5 g of trans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in Example 1, was added dropwise. After the temperature was reduced to room temperature and stirring was carried out for 3 20 hours, water and hexane were added. The organic phase was separated, rinsed with water, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. 12.1 g of the oily substance obtained was purified by silica gel column chromatography (hexane), and 4.0 g of trans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene as an oily substance was obtained.

The following compounds were prepared in the same manner as mentioned above:

trans-6-(4-fluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,4-difluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,4,5-trifluorophenyl)-trans-2-vinyldecahydronaphthalene, .0 trans-6-(4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-tr'ifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene.

Example 7: Synthesis of trans-6-(3,4,5-trifluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene F
OHC PhP=CHCH3 CH3-CH=CH
F -~ O F
F F

13.4 g of ethyltriphenylphosphonium bromide was suspended in 30 ml of THF. While the suspension was cooled to 10 C or lower, a 25 ml THF solution of 4.5 g of potassium t-biatoxide was added dropwise. While the cooling was further continued, 50 ml THF solution of 10.1 g of trans-6-(3,4,5-trifluorophenyl)-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in a manner similar to that of Example 1, was added dropwise. After the temperature was reduced to room temperature and stirring was carried out for 3 hours, water and hexane were added. The organic phase was separated, rinsed with water, and dried on anhydrous sodium sulfate.
Then, the solvent was evaporated. 9.1 g of the oily substance obtained was dissolved in 50 ml of toluene. 2.5 g of sodium benzenesulfinate and 10 ml of 10% hydrochloric acid were added to the solution, and the mixture was heated under refluxing for 20 hours. The temperature was reduced to room temperature. The organic phase was extracted using toluene, rinsed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The resultant was purified by silica gel column chromatography (hexane), and recrystallized (in ethanol) to obtain 7.8 g of white solid trans-6-(3,4,5-trifluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene (1-6).

The following compounds were prepared in the same manner as mentioned above:

0 trans-6-(3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,4-difluorophenyl)-trans-2-(1-.5 propenyl)decahydronaphthalene, trans-6-(4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, ?0 trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(l-25 propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,4,5-trifluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,4-difluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, t ran s-6- (3, 5-difluoro-4-trifluoromethoxyphenyl) -trans -2-vinyldecahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-vinyldecahydronaphthalene, 5 trans-6-(4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-vinyldecahydronaphthalene, 10 trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene, 15 trans-6-(3,4,5-trifluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3,5-difluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-(1-20 pentenyl)decahydronaphthalene, trans-6-(3,4-difluorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(4-trifluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, 25 trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6- (3, 5-dif luoro-4-trif luoromethoxyphenyl) -trans-2- (1-.pentenyl)decahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(1-pentenyl)decahydronaphthalene.

Example 8: Synthesis of trans-6- (3, 4 -dif luorophenyl) -trans -2-(3-butenyl)decahydronaphthalene OHC-(CH2 p-3p-CH2 F ---i F
CHZ=CH-(CHZh O
F

16.5 g of inethyltriphenylphosphonium iodide was suspended in a mixture of 17 ml THF and 51 ml toluene. While the suspension was cooled to 10 C or lower, a 4.6 g of potassium t-butoxide was added. While the cooling was further continued, 20 ml toluene solution of 5.0 g of trans-6-(3,4-difluorophenyl)-trans-2-(2-formylethyl)decahydronaphthalene, which was obtained in Example 2, was added dropwise. After the mixture was stirred for 2 hours, 5 ml of water and then 200 ml of hexane were added, and triphenylphosphine oxide was separated by filtration. The organic phase was separated, 0 rinsed with 100 ml of water and 100 ml of water/methanol mixed solvent (1/2), and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The oily substance obtained was purified by silica gel column chromatography (hexane) and recrystallized from ethanol to obtain 3.7 g of white solid .5 trans-6-(3,4-difluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene (1-5).

The following compounds were prepared in the same manner as mentioned above:

trans-6-(3,5-difluorophenyl)-trans-2-(3-?0 butenyl)decahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,4,5-trifluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, 25 trans-6-(4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,4,5-trifluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,5-difluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(4-fluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,4-difluorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-trifluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(4-difluoromethoxyphenyl)-trans-2-(3-L0 pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-difluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-difluoromethoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(4-chiorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-chlorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-chlorophenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methoxyphenyl)-trans-2-(3-pentenyl)decahydronaphthalene.

Example 9: Synthesis of trans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene F

BrM O
F
Pr F p-Ts OH Pr O

F
F F
H2, Pd~ ~--BuoK= Pr 1) BuLi Pr 2) Cp2 COOH
F
F F
soci NH3-- PoCi3 Pr -11 O
CN
F

(9-a) Synthesis of trans-2-propyl-trans-6-(3,5-difluorophenyl)-trans-decahydronaphthalene 5 2.4 g of magnesium was suspended in 5 ml of tetrahydrofuran, and an 80 ml THF solution of 17.6 g of 1-bromo-3,5-difluorobenzene was added dropwise to the suspension over a period of about 30 minutes at such a rate that the THF
was moderately refluxed. After further stirring the mixture 10 for 1 hour, an 80 ml THF solution of 20 g of 6-propyloctahydro-2-naphthalenone was added dropwise over a period of 30 minutes. After further stirring the mixture for 2 hours, 80 ml of 10% hydrochloric acid was added. 100 ml of hexane was added, and the organic phase was separated. The 15 aqueous phase was extracted with 100 ml of hexane, and the extracts were combined with the organic phase. The combined organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and 105 ml of toluene and 1.7 g of p-toluenesulfonic acid monohydrate were added. The mixture was heated at 110 C with stirring while evaporated water was separated and removed. When the evaporation of water was stopped, the temperature was reduced to room temperature. 50 ml of water was added, and the organic phase was separated.
The organic phase was rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent _0 was evaporated, and the whole amount of the residue was dissolved in 100 ml of ethyl acetate. 3.0 g of carbon with 5%
palladium was added, and the mixture was stirred in an autoclave in hydrogen under a pressure of 400 KPa. After stirring for 5 hours at room temperature, the catalyst was removed by way of filtration through celite, and the solvent was evaporated to obtain a trans/cis mixture of trans-6-propyl-2-(3,5-difluorophenyl)-trans-decahydronaphthalene. The whole amount of this mixture was dissolved in 100 ml of N,N -dimethylformamide (DMF). 2.4 g of potassium t-butoxide was added to the solution, and the mixture was stirred for 5 hours at 70 C. After the mixture was cooled to room temperature, 100 ml of water was added, and extraction was performed tw ice using 100 ml of toluene. Organic phases were combined, and the combined organic phase was rinsed with 10% hydrochlori c acid, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane), and recrystallized from ethanol to obtain 16.5 g white crystals of trans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene.

(9-b) Synthesis of trans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene 16.5 of trans-6-propyl-trans-2-(3,5-difluorophenyl)-trans-decahydronaphthalene, which was obtained in (9-a), was dissolved in 70 ml of THF, and the solution was cooled to -78 C. 38.6 ml of 1.6 M butyl lithium-hexane solution was added over a period of 30 minutes in a manner such that the inner temperature does not exceed -50 C. After further stirring for 20 minutes, maintaining the inner temperature under -50 C, carbon dioxide was injected into the mixture.
When generation of heat stopped, the temperature was gradually increased to room temperature. 50 ml of water and 50 ml of hexane was added, and the organic phase was separated. The organic phase was rinsed with water and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the whole amount of the residue was dissolved in 170 ml of 1,2-dichioroethane. 8.1 g of thionyl chloride and 0.1 ml of pyridine were added, and the mixture was stirred for 5 hours. The solvent was evaporated, and the whole amount of the residue was dissolved in 100 ml of dichloromethane. Ammonia gas was injected into the solution while stirring. Two hours later, the solution was filtered.

The residue was dissolved in 100 ml of DMF, and 7.9 g of oxalyl chloride was added dropwise. After further stirring for 1 hour, the mixture was poured onto iced water. 100 ml of toluene was added, and the organic phase was separated. The organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography and recrystallized from ethanol to _0 obtain 9 g white crystals of trans-2-propyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.
The following compounds were prepared in the same manner as mentioned above:

trans-2-methyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-ethyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-butyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-pentyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-hexyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-heptyl-trans-6-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.

Example 10: Synthesis of trans-2-propyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene F
Pr HBr, AcOH Pr OMe -' O OH
F
Tf20 Pr OTf F
KCN, NiBr2(PPh3)2 PPh3, Zn Pr 10 O CN

20 g of trans-2-propyl-trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene (which is a compound obtained in a manner similar to (1-a) except that 1-bromo-3 -fluro-4-methoxybenzene was used instead of 1-bromo-3,5-difluorobenzene) was added to a mixture of 100 ml of acetic acid and 100 ml of 48% aqueous solution of hydrobromic acid, and the mixture was heated for 20 hours under refluxing. The temperature was reduced to room temperature. Water and toluene were added to the mixture, and the organic phase was separated. The organic phase was rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the whole amount of the residue was dissolved in 100 ml of dichloromethane. 19.7 g of trifluromenthanesulfonic anhydride was added to the solution, and the mixture was cooled to 5 C. While the mixture was stirred forcefully, 12 ml of pyridine was added dropwise, and thereafter the mixture was further stirred f o r 1 hour. Water was added to stop the reaction. The organic phase was separated out, and the aqueous phase was extracted with dichloromethane. Organic phases were combined, and the combined organic phase was rinsed with 10% hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, water, and then a saturated saline solution, and dried on anhydrous sodium sulfate. After the solution was purified by silica gel column chromatography (hexane), the solvent was evaporated. The whole amount of the residue was dissolved in 150 ml of acetonitrile. 1.7 g of 0 dibromobis(triphenylphosphine)nickel(II), 1.4 g of triphenylphosphine, 0.3 g of zinc powder, and 8.5 g of potassium cyanide were added to the solution, and the mixture was heated at 80 C for 16 hours while stirring. Water was added to stop the reaction. The organic phase was further 5 rinsed with water, and dried on anhydrous sodium sulfate. The solution was purified by silica gel column chromatography (hexane/dichloromethane), and further recrystallized from ethanol to obtain 12.5 g of white solid 5-fluoro-6-cyano-2-(trans-4-propylcyclohexyl)naphthalene.

'.0 The following compounds were prepared in the same manner as mentioned above:

trans-2-methyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-ethyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-25 decahydronaphthalene, trans-2-butyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-pentyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-hexyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-heptyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-vinyl-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-(1-propenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-(1-pentenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-(3-butenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene, trans-2-(3-pentenyl)-trans-6-(3-fluoro-4-cyanophenyl)-trans-decahydronaphthalene.

Example 11: Synthesis of trans-6-(4-cyano-3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene CH3-CH=CH 1) BuLi 1) SOCIZ POCI3 2)C~g 2)NH ( )=~-F
F CH3-CH=CH
O CN
F
4.8 ml of a 1.5 M hexane solution of n-butyl lithium was added dropwise to a 10 ml THF solution of 1.74 g of trans- 6-(3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene while cooling the solution to -78 C. After stirring for 10 minutes, carbon dioxide was injected into the mixture until saturation. After the mixture was left to stand until the temperature reached room temperature, 10% hydrochloric acid was added. The organic phase was extracted using ethyl acetate, rinsed with water, and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated. 1.9 g of the solid substance obtained was suspended in 12 ml of 1,2-ethylene dichloride. 1.4 g of thionyl chloride, 0.05 ml of pyridine, 0 and 1 ml of N,N-dimethylformamide (DMF) were added to the suspension, and the mixture was stirred for 1 hour at room temperature. The solvent was evaporated, and the oily substance obtained was dissolved in 50 ml of methylene chloride. Ammonia gas was injected into the solution while .5 cooling the solution to 10 C or lower until saturation. After stirring for 1 hour at room temperature, the solvent was evaporated. 2.6 g of the solid substance obtained was suspended in 20 ml of DMF. 1.5 ml of phosphorus oxychloride was added to the suspension while cooling the suspension to ?0 10 C or lower, and the mixture was stirred for 1 hour at room temperature. Water was added to the mixture. The organic phase was extracted using toluene, rinsed with a saturated saline solution, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The residue was purified by 25 silica gel column chromatography (hexane), and recrystallized (ethanol) to obtain 0.3 g of white solid trans-6-(4-cyano-3,5-difluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene (I-12) The following compounds were prepared in the same manner as mentioned above:

trans-2-vinyl-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene, trans-2-(1-propenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene, trans-2-(1-pentenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene, trans-2-(3-butenyl)-trans-6-(4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene, -trans-2-(3-pentenyl)-trans-6--{4-cyano-3,5-difluorophenyl)-trans-decahydronaphthalene.

Example 12: Synthesis of trans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene F
Ph3P~H-{( )}-F F
1) Ph3P=CHOCH3 ` =(F O

O 2) HG - C3 O-s C3 -cb F
3) NaOH
F
~b=Po - C.3 O F

F

(12-a) Synthesis of 6-propyl-trans-decahydronaphthalene-2-carbaldehyde A 100 ml THF solution of 24 g of 6-propyl-trans-decahydro-2-naphthalenone was added dropwise to a Wittig reagent prepared from 38 g of methoxymethyltriphenylphosphonium chloride and 14 g of potassium t-butoxide in 200 ml of THF, while the mixture was cooled 10 C or lower. The temperature was reduced to room temperature. After the mixture was stirred for 4 hours, water and hexane were added. The organic phase was separated and rinsed with water, and the solvent was evaporated. The pale yellow oily substance obtained was dissolved in 180 ml of T H F.
180 ml of 10% hydrochloric acid was added to the solution, and the mixture was heated for 3 hours under refluxing. The temperature was reduced to room temperature, the organic phase .0 was separated, and the aqueous phase was extracted with ethyl acetate. Organic phases were combined, the combined organic phase was rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence, and the solvent was evaporated. The pale yellow L5 solid substance obtained was dissolved in 160 ml of inethano 1.
20 ml of 10% aqueous solution of sodium hydroxide was added to the solution while cooling the solution to 10 C or lower.
After stirring the mixture for 2 hours, the temperature was reduced to room temperature, and the solvent was evaporate d.

?0 The pale yellow solid substance obtained was rinsed with water, and recrystallized from a hexane solution to obtain 18 g of white solid 6-propyl-trans-decahydronaphthalene-2-carbaldehyde.

25 (12-b) Synthesis of 2-[2-(3,4,5-trifluorophenyl)ethenyl]- 6-propyl-trans-decahydronaphthalene A 90 ml THF solution of 18 g of 6-propyl-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in (12-a), was added dropwise to a Wittig reagent prepared from 49 g of 3,4,5-trifluorobenzyltriphenylphosphonium bromide and 12 g of potassium t-butoxide in 250 ml of THF, while the mixture was cooled to 10 C or lower. The temperature was reduced to room temperature. After the mixture was stirred for 4 hours, water and hexane were added. The organic phase was separated and rinsed with water, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane) to obtain 22 g of 2-[2-(3,4,5-trifluorophenyl)ethenyl]-6-propyl-trans-decahydronaphthalene as a colorless--oily substance.

(1-c) Synthesis of trans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene 22 g of 2-[2-(3,4,5-trifluorophenyl)ethenyl]-6-propyl-trans-decahydronaphthalene, which was obtained in (12-b), was dissolved in 120 ml of ethyl acetate. 5 g of carbon with 5%
palladium was added to the solution. Hydrogenation was carried out at room temperature for 6 hours. The catalyst was removed by way of filtration through celite, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane), and recrystallized from ethanol at -70 C or lower to obtain 6 g of white solid trans-6-propyl-2-[2-(3,4,5-trifluorophenyl)ethyl]-trans-decahydronaphthalene.
The following compounds were prepared in the same manner as mentioned above:

trans-6-propyl-2-[2-(3,5-difluorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(4-fluorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3,4-difluorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(4-trifluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl]-L0 trans-decahydronaphthalene, trans-6-propyl-2-[2-(3,5-difluoro-4-trifluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3-fluoro-4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3,5-difluoro-4-difluoromethoxyphenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(4-chlorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3-fluoro-4-chlorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(3,5-difluoro-4-chlorophenyl)ethyl]-trans-decahydronaphthalene, trans-6-propyl-2-[2-(4-methoxyphenyl)ethyl]-trans-decahydronaphthalene, trans -6-propyl-2- [2- (3-fluoro-4-methoxyphenyl) ethyl] -t ran s-decahydronaphthalene, trans-6-propyl-2-[2-(3,5-difluoro-4-methoxyphenyl)ethyl]-trans-decahydronaphthalene.

Example 13: Synthesis of 4-cyano-3-fluorophenyl-6-pentyl-trans-decahydronaphthalene-2-carboxylate (1-14) 1) Ph3P=CHOCH3 KMn04 CSHi~
O 2) HC - CsH, t O-> C5Hjj OH
I
3) NaOH O
1) SOCIZ
im F CsK I CN
2) FrO-6CN O

(13-a) Synthesis of 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde Reaction of 28 g of 6-propyl-trans-decahydro-2-naphthalenone with a Wittig reagent similar to that used in (1-a) was carried out to obtain 19 g of white solid 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde.
(13-b) Synthesis of 6-pentyl-trans-decahydronaphthalene-2-carboxylic acid 19 g of 6-pentyl-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in (13-a), was added dropwise to a 60 ml aqueous solution of 12 g of concentrated sulfuric acid and 6 g of potassium permanganate while the mixture was cooled to 10 C or lower. After stirring the mixture for 30 minutes at room temperature, water and ethyl acetate were added. The organic phase was separated and rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence. After the organic phase was dried on anhydrous sodium sulfate, the solvent was evaporated. The residue was recrystallized from a hexane solution to obtain 8 g white solid 6-pentyl-trans-decahydronaphthalene-2-carboxylic acid.

(13-c) Synthesis of 4-cyano-3-fluorophenyl-6-pentyl-trans-decahydronaphthalene-2-carboxylate l0 8 g of 6-pentyl-trans-decahydronaphthalene-2-carboxylic acid, which was obtained in (13-b), was dissolved in 40 ml of 1,2-dichloroetha-n-e. 5 g of thionyl-chloride, 0.1 ml of pyridine, and 5 ml of DMF were added to the solution, and the mixture was heated for 1 hour under refluxing. After excessive thionyl chloride was evaporated, 50 ml of dichloromethane was added, then 4 g of 3-fluoro-4-cyanophenol and 3 g of pyridine were added, and the mixture was stirred for 8 hours at room temperature. 10% hydrochloric acid was added, and the organic phase was separated and rinsed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. After the solvent was evaporated, the residue was purified by silica gel chromatography (hexane/ethyl acetate), and recrystallized from ethanol to obtain 3 g white crystals of 4-cyano-3-fluorophenyl 6-pentyl-trans-decahydronaphthalene-2-carboxylate.

Example 14: Synthesis of 4-cyano-3,5-difluorophenyl 6-propyl-trans-decahydronaphthalene-2-carboxylate (1-13) 1) Ph3P=CHOCH3 Cr03 C3H7 - O --. ~F-h OH
O 2) HC ~~
-cb- 3) NaOH O

1)S?10 F C3 O CN
2) Fi0-(( )}-CN O F
~=(F

In a manner similar that in (13-c), esterification reaction of 15 g of 6-propyl-trans-decahydronaphthalene-2-carboxylic acid, which was obtained in (13-b), with 11 g of 3,5-difluoro-4-cyanophenol was carried out to obtain 6 g of white solid 4-cyano-3,5-difluorophenyl-6-propyl-trans-decahydronaphthalene-2-carboxylate.

Example 15: Synthesis of 6- (4 -vinyl -trans-cyclohexyl) -2- (3, 5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene (I-15) F
O BrMlg-(( )) CO
O O ~~=-CF CO O ~ -2) Hr Pd-C
3) (HOCIil)2, H' F
CO F F
O O -s O~_< 1)P sFK)CFb 2) HCI
F 3) NaOH
F F
Ph3P=CI42 O 1) M9 O -- -~
2) C02(g) F F F FCN
OH 1}$OC1Z POC13 O
IN rO
0 2) ~(9 ) i F F
(15-a) Synthesis of 4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-ylJcyclohexanone ethyleneacetal Reaction of 29 g of 4-[6-oxo-trans-octahydronaphthalen-2-yl]cyclohexanone monoethyleneacetal with a Grignard reagent prepared from 3,5-difluoro-l-bromobenzene was carried out, and dehydration and re-acetalization were carried out to obtain 33 g of pale yellow solid 4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanone ethyleneacetal.

(15-b) Synthesis of 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone ethyleneacetal Catalytic hydrogenation reduction of 33 g of 4-[2-(3,5-difluorophenyl)-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-6-yl]cyclohexanone ethyleneacetal, which was obtained in (15-a), was carried out to obtain 29 g of pale yellow solid 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone ethyleneacetal.

(15-c) Synthesis of 4-[6-(3,5-difluorophenyl) -trans-decahydronaphthalen-2-yl]cyclohexanone Deacetalization of 29 g of 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone ethyleneacetal, which was obtained in (5-b), was carried out to obtain 20 g of pale yellow solid 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl)cyclohexanone.

(15-d) Synthesis of 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexylcarbaldehyde Reaction of 20 g of 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanone, which was'obtained in (5-c), with a Wittig reagent was carried out to obtain 18 g of pale yellow solid 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanecarbaldehyde.
(15-e) Synthesis of 6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene Reaction of 18 g of 4-[6-(3,5-difluorophenyl)-trans-decahydronaphthalen-2-yl]cyclohexanecarbaldehyde, which was obtained in (15-d), was carried out to obtain 16 g of white solid 6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene.

(15-f) Synthesis of 3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-y1]benzoic acid Reaction of 16 g of 6-(3,5-difluorophenyl)-2-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalene, which was obtained in (15-e), with butyl lithium was carried out, and thereafter reaction of the resultant with carbon dioxide was carried out to obtain 16 g of milky-white solid 3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-yl]benzoic acid.

(15-g) Synthesis of 6-(4-vinyl-trans-cyclohexyl)-2-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene 16 g of 3,5-difluoro-4-[6-(4-vinyl-trans-cyclohexyl)-trans-decahydronaphthalen-2-yl]benzoic acid, which was obtained in (15-f), was dissolved in 80 ml of 1,2-dichloroethane. 6 g of thionyl chloride, 0.1 ml of pyridine, and 3 ml of DMF were added to the solution, and the mixture was stirred for 6 hours at room temperature. After the solvent and excessive thionyl chloride were evaporated, 120 ml of dichloromethane was added, and ammonia gas was injected while the mixture was cooled to 0 C. When generation of heat stopped, the mixture was stirred for 2 hours at room temperature, and crystals which precipitated were separated by precipitation. -The---ye-llow crystals obtained were dissolved in 140 ml of DMF. 11 g of oxalyl chloride was added dropwise to the solution while the mixture was cooled to 0 C. After stirring for 1 hour at room temperature, the mixture was poured-onto iced water, and extraction was carried out using toluene. The organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (toluene) and recrystallized from ethanol to obtain 3 g white crystals of 6-(4-vinyl-trans-cyclohexyl)-2-(3,5-difluoro-4-cyanophenyl)-trans-decahydronaphthalene.
The following compounds were prepared in the same manner as.mentioned above:

6- (trans- 1-propenyl) -2- [trans-4- [3, 5-dif luoro-4- (trans-2-butenyloxy)phenyl]cyclohexyl)-trans-decahydronaphthalene, 6-(trans-3-butenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl)cyclohexyl)-trans-decahydronaphthalene, 6-(trans-3-pentenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene, 6-(trans-l-pentenyl)-2-[trans-4-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]cyclohexyl]-trans-decahydronaphthalene.
Example 16: Synthesis of trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene (1-20) (~~ MgBr CsH~~ ~/ _ _-~ CsHt~ O +CsF.{+1 O
O

Hz 'BuOK CsH,, -~ -i O
F
(HO
)z6 O F
CSHii IZ! HIO4 CSHI1 _IN O I Pd( CSFiit O O F

F

(16-a) Synthesis of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene To a suspension of 23.6 g of metal magnesium in 90 ml of THF, a 700 ml THF solution of 150 g of bromobenzene was added dropwise to obtain a Grignard reagent. A 400 ml THF solution of 217 g of 6-pentyl-trans-decahydro-2-naphthalenone was added dropwise to the reagent over a period of 30 minutes. After further stirring for 2 hours, 400 ml of 10% hydrochloric acid was added. Then, the organic phase was separated, rinsed with water, and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated. 261 g of the oily substance obtained was dissolved in 800 ml of toluene. 13 g of p-toluenesulfonic acid monohydrate was added to the solution, and the mixture was heated for 4 hours under refluxing using an apparatus equipped with a water separator until evaporation of water stopped. Then, the solution was cooled to room temperature.

Water was added to the solution, and the organic phase was separated, rinsed with a saturated saline solution, and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated. 240 g of the oily substance obtained was dissolved in 1 1 of ethyl acetate in an autoclave. 24 g of carbon with 5% palladium was added to the solution. Catalytic hydrogenation reduction was carried out for 5 hours at room temperature. Then, the solution was filtered through celite to separate the catalyst, and the solvent was evaporated to obtain 207 g of cis/trans mixture of 2-phenyl-6-pentyl-tra n s-decahydronaphthalene. The whole amount of this mixture was dissolved in 630 ml of DMF. 45 g of potassium t-butoxide was added to the solution, and the mixture was heated for 2 ho u rs under refluxing. The mixture was cooled to room temperature, water was added to the mixture, and extraction was carried out using hexane. The organic phase was rinsed with a saturat e d saline solution, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by s i l ica gel column chromatography (hexane) and recrystallized from ethanol to obtain 24 white crystals of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentioned above:

trans-2-phenyl-6-methyl-trans-decahydronaphthalene, trans-2-phenyl-6-ethyl-trans-decahydronaphthalene, trans-2-phenyl-6-propyl-trans-decahydronaphthalene, trans-2-phenyl-6-butyl-trans-decahydronaphthalene, trans-2-phenyl-6-hexyl-trans-decahydronaphthalene, trans-2-phenyl-6-heptyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-methyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-ethyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-propyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-butyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-(4-chlorophenyl)-6-hexyl-trans-decahydronaphthalene, trans-2- (4-chlorophenyl) -6-heptyl-trans-decahydronaphthalene, trans-2- (4-methoxyphenyl) -6-methyl-trans-decahydronaphthalene, trans-2-(4-methoxyphenyl)-6-ethyl-trans-decahydronaphthalene, trans-2- (4-methoxyphenyl) -6-propyl-trans-decahydronaphthalene, trans-2-(4-methoxyphenyl)-6-butyl-trans-decahydronaphthalene, trans-2- (4-methoxyphenyl) -6-pentyl-trans-decahydronaphthalene, trans-2-(4-methoxyphenyl)-6-hexyl-trans-decahydronaphthalene, trans-2- (4-methoxyphenyl) -6-heptyl-trans-decahydronaphthalene, trans-2- (4-hydroxyphenyl) -6-methyl-trans-decahydronaphthalene, trans-2- (4-hydroxyphenyl) -6-ethyl-trans-decahydronaphthalene, trans-2-(4-hydroxyphenyl)-6-propyl-trans-decahydronaphthalen e, trans-2-(4-hydroxyphenyl)-6-butyl-trans-decahydronaphthalene, trans-2-(4-hydroxyphenyl)-6-pentyl-trans-decahydronaphthale n e, trans-2-(4-hydroxyphenyl)-6-hexyl-trans-decahydronaphthalen e, trans-2-(4-hydroxyphenyl)-6-heptyl-trans-decahydronaphthale n e, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl)-6-meth yl-trans-decahydronaphthalene, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl)-6-ethy 1-trans-decahydronaphthalene, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-prop yl-trans-decahydronaphthalene, trans-2_-[4=(414-dimethy1-1,3-oxazolidin-2-yl)phenyl)-6-but y 1-trans-decahydronaphthalene, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-pent yl-trans-decahydronaphthalene, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2=y1)phenyl]-6-hept yl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-l,3-oxazolidin-2-yl)phenyl)-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phen y 1)-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phen y 1]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phen y 1]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-l,3-oxazolidin-2-yl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4,4-dimethyl-l,3-oxazolidin-2-yl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-methyl-trans-decahydronaphthalen e, trans-2-(3-fluorophenyl)-6-ethyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-propyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-butyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-hexyl-trans-decahydronaphthalene, trans-2-(3-fluorophenyl)-6-heptyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-methyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-ethyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-propyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-butyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-(3,5-difluorophenyl)-6-hexyl-trans-decahydronaphthalerie, trans-2-(3,5-difluorophenyl)-6-heptyl-trans-decahydronaphthalene, trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-phenyl-6-pentyl-trans-decahydronaphthalene.
(16-b) Synthesis of trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene 227 g of trans-2-phenyl-6-pentyl-trans-decahydronaphthalene, which was obtained in (16-a), was dissolved in 80 ml of 1,2-dichloroethane and 670 ml of acetic acid. 125 g of iodine and 91 g of orthoperiodic acid were added, and then 180 ml of 10% sulfuric acid was added. After the mixture was heated for 1.5 hours under refluxing, the mixture was cooled to room temperature, and extraction was carried out using toluene. Then, the organic phase was rinsed with a saturated aqueous solution of sodium hydrogensulfite and a saturated saline solution, in sequence, and dried on anhydrous magnesium sulfate. After the solvent was evaporated, the residue was recrystallized from ethanol/toluene to obtain 254 g white crystals of trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene.

(16-c) Synthesis of trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene g of trans-2-(4-iodophenyl)-6-pentyl-trans-decahydronaphthalene, which was obtained in (16-b), was 25 dissolved in a mixed solution of 48 ml of toluene and 24 ml of ethanol. 0.8 g of tetrakis(triphenylphosphine)palladium(0) and 48 ml aqueous solution of 2 M sodium carbonate were added to the mixture, and 32 ml ethanol solution of 16 g of 3,4,5-trifluorophenylboric acid was further added dropwise over a period of 10 minutes. After heating the mixture for 24 hours at 70 C while stirring, the mixture was cooled to room temperature, and water was added to the mixture. After extraction was carried out using toluene, the organic phase was rinsed with a saline solution and dried on anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane) and recrystallized from ethanol to obtain 18 g whi t e crystals of trans-2-[4-(3,4,5-trifluorophenyl)phenyl)-6-pentyl-t-rans-decahydronaphthalene. -The following compounds were prepared in the same manner as mentioned above:

trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-methyl-trans-decahydronaph-thalene, trans-2-[4-(3,4,5-trifluorophenyl)phenyl)-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,4,5-trifluorophenyl)phenyl)-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,4,5-trifluorophenyl)phenyl)-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,4,5-trifluorophenyl)phenyl)-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-(4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-l0 decahydronaphthalene, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthale-n-e, trans-2-[4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-.decahydronaphthalene, trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2- [3-fluoro-4- (3, 4-difluorophenyl)phenyl] -6-butyl-t ran s-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans -2- (3-fluoro-4- (3, 4-difluorophenyl) phenyl] -6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2--[3-fluor-o-4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl)-6-butyl-trans-decahydronaphthalene,_..____ trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2 -[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans=decahydronapht-halene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-(3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene;

trans-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl] -6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, -tran-s-2-[3-fluoro-4-(4-chlorophenyl)phenyll-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, , trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl)-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-(4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4--[4-(2,2-,2-trifluoroethoxy).phenyl]phenyl)-6-propyl-trans-decahydronaphthalene, trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl) -6-butyl-trans-decahydronaphthalene, trans-2-[4=44-(2,2;-2=trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl)phenyl)-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)pheny1]-6-ethyl-trans-decahydronaphthalene, trans-2-(4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronapht-halene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)pheny1]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl)-6-heptyl-trans-decahydro.naphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]pheny1]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]--6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-(4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2- [4- [3-fluoro-4- (1, 1,2, 2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2- [4- [3-fiuoro-4- (1, 1, 2, 2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, -trans-2-[_4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2- [4- [3, 5-difluoro-4- (2, 2, 2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2- [4- [3, 5-difluoro-4- (2, 2, 2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2--tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2- [ 4- [3, 5-difluoro-4- (1, 1, 2, 2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-(3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl)-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl)-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene;

trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, .. 142 trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl 6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyi]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, ' trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethox.y)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)phenyl)-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-(3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenylJ-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-methoxyphenyl.)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans -decahydronaphthalene, trans-2-[4-(3-fiuoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans -decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl)-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-(4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-(4-(3-fluoro-4-benzyloxyphenyl)phenyl)-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyll-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4=(3-fluoro-A-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, traris-2-[4-(4-ethoxyphenyl)phenyl)-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-ethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(2,3-difluoro-4-ethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-allyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-methylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-ethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-(4-propylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenylj-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl) -6-methyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl~phenyl]-6-ethyl-trans-decahydronaphthalene, 15~
trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6;hexyl-trans-decahydronaphthalene, trans-2-[4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-l,3-oxazolin-2-yl)phenyl]phenyl] -6-propyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl 6-heptyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-l,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro=4-(4,4=dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2- [4- [3, 5-dif luoro-4- (4, 4-dimethyl-1, 3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-(3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-(3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3-fluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene.

Example 17: Synthesis of trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene (I-21) F
C3Hz F n-BuLi h - GeH7 BrMg-{( )}-F
~/
Pd(PPh3)4 F F
F F

F

(17-a) Synthesis of trans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene 50 ml of 1.5 M hexane solution of n-butyl lithium was added dropwise to a 100 ml THF solution of 17 g of trans-2-(3,5-difluorophenyl)-6-propyl-trans-decahydronaphthalene, which was cooled to -45 C, over a period of 10 minutes. After stirring the mixture for 30 minutes, the temperature was increased to room temperature, and water was added. A 10%
aqueous solution of sodium hydrogen sulfite was added until the color of iodine was not observed. The organic phase was extracted using hexane, rinsed with a saturated saline solution, and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain 23 g of white solid trans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene.

(17-b) Synthesis of trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene 23 g of trans-2-(3,5-difluoro-4-iodophenyl)-6-propyl-trans-decahydronaphthalene, which was obtained in (17-a), was dissolved in a mixed solution of 38 ml of toluene and 20 ml of ethanol. 1.2 g of tetrakis(triphenylphosphine)palladium(0) and 37 ml aqueous solution of 2 M sodium carbonate were added to the mixture, and 10 ml ethanol solution of 11 g of 3,4-difluorophenylboric acid was further added dropwise over a period of 10 minutes. After heating the mixture for 18 hours at 70 C while stirring, the mixture was cooled to room temperature, and water was added to the mixture. After extraction was carried out using toluene, the organic phase was rinsed with a saline solution and dried on anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography and recrystallized three times from ethanol to obtain 11 g white crystals of trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentioned above:

trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-(3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans -2- [3, 5-difluoro-4- (3, 4, 5-trifluorophenyl) phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-pen-tyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, t ran s-2- [ 3, 5-dif luoro-4- (3, 5-difluorophenyl)phenyl] -6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans -2- [3, 5-dif luoro-4- (3-f luorophenyl)phenyl] -6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4=-trifluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans -2- [3, 5-dif luoro-4- (4-difluoromethoxyphenyl) phenyl] -6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-difluor.omethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4--difluoromethoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-ethylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-propylphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2- [3, 5-dif luoro-4- (4-methoxyphenyl) phenyl] -6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, t ran s-2- [3, 5-difluoro-4- (4 -ben zyloxyphenyl) phenyl] -6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans -2- [3, 5-dif luoro-4- (3-fluoro-4 -ben zyloxyphenyl) phenyl] -6-methyl-trans-decahydronaphthalene, trans -2- [3, 5-difluoro-4- (3-fluoro-4 -ben zyloxyphenyl)phenyl] -6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl)-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3-fluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-(3,5-difluoro-4-benzyloxyphenyl)phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(trans-3-pentenyl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans -2- [3, 5-difluoro-4- [4- (4, 4-dimethyl-1, 3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-y1)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3-fluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-methyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-ethyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-propyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-butyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-pentyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-hexyl-trans-decahydronaphthalene, trans-2-[3,5-difluoro-4-[3,5-difluoro-4-(4,4-dimethyl-1,3-oxazolin-2-yl)phenyl]phenyl]-6-heptyl-trans-decahydronaphthalene.

Example 18: Synthesis of 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid C3H7 N~_ HCI _C3H7 O
COOH
O

28 g of trans-2-[4-(4,4-dimethyl-1,3-oxazolidin-2-yl)phenyl]-6-trans-propyldecahydronaphthalene was dissolved in 140 ml of THF. The solution was heated for 4 hours under refluxing, and then the temperature was reduced to room temperature. The organic phase was separated, rinsed with a saturated saline solution and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain 23 g of 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid The following compounds were prepared in the same manner as mentioned above:

4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoic acid, 4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoic acid, 4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoic acid, 4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoic acid, 4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoic acid, 4-(trans-6-heptyl-trans-decahydronaphthalen-2 -yl)benzoic acid, 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoic acid, 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoic acid.

Example 19: Synthesis of 3-fluoro-4-cyanophenyl 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate F
~H7 5~12 HO CN ~~
~/ ~
O COOH - ~ -i O F
COO-~( )}-CN
Pd(PPh3)4 ~/

22 g of 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoic acid, which was obtained in Example 18, was dissolved in 110 ml of dichioromethane. 17 g of thionyl chloride, 0.1 ml of pyridine, and 10 ml of DMF were added to the solution, and the mixture was heated for 1 hour under refluxing. After excessive thionyl chloride was evaporated, 110 ml of dichloromethane was added, then 10 g of 3-fluoro-4-cyanophenol and 10 g of pyridine were added, and the mixture was stirred for 8 hours at room temperature. 10% hydrochloric acid was added, and the organic phase was separated and rinsed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. After the solvent was evaporated, the residue was purified by silica gel chromatography (hexane/ethyl acetate), and recrystallized from ethanol to obtain 23 g white crystals of 3-fluoro-4-cyanophenyl 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate.

The following compounds were prepared in the same manner as mentioned above:

3-fluoro-4-cyanophenyl 4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-methyl-tran s-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-ethyl-trans -decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-butyl-trans -decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3-fluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-cyanophenyl 3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3,5-difluoro-4-cyanophenyl 3,5-difluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-fluorophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethoxyphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethylphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethylphenyl 3-fluora-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethylphenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethylphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethylphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethyiphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-trifluoromethyiphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4-difluorophenyl 3-fluoro-.4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 3,4,5-trifluorophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 3-4-methylphenyl fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methylphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-ethylphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-methoxyphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-(3-butenyl)phenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-phenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-chlorophenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-methyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-ethyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-propyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-butyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-pentyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-hexyl-trans-decahydronaphthalen-2-yl)benzoate, 4-allyloxyphenyl 3-fluoro-4-(trans-6-heptyl-trans-decahydronaphthalen-2-yl)benzoate.

Example 20: Synthesis of 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene (1-27) F
BrMg O O
F
TsOH O F
O --~ -~ O
F
HZ t-BuOK F
Pd-C F

(20-a) Synthesis of 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene Reaction of 12 g of 6-propyldecahydro-2-naphthalenone with a Grignard reagent prepared from 1,2-difluoro-6-bromonaphthalene and dehydration were carried out to obtain 15 g of pale yellow liquid 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene.

(20-b) Synthesis of 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene Catalytic hydrogenation reduction and isomerization of 15 g of 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-1,2,3,4,7,8,9,10-octahydronaphthalene, which was obtained in (20-a), were carried out to obtain 3 g of white solid 6-(1,2-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentioned above:

6-(2-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6- (2-f luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6-(2-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,2-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6- (2, 3-dif luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,2,3-trifluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6- (1, 7-dif luoronaphthalen-3-yl) -2-pentyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,7-difluoronaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2 -methyl -trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2-propyl-trans-decahydronaphthalene, 6-(1,2,8-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2-pentyl-trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2-hexyl-trans-decahydronaphthalene, 6- (1, 2, 8-trif luoronaphthalen-6-yl) -2-heptyl-trans-decahydronaphthalene, 6- (1, 6, 7-trif luoronaphthalen-6-yl) -2-methyl-trans-decahydronaphthalene, 6- (1, 6, 7-trif luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6- (1, 6, 7-trifluoronaphthalen-6-yl) -2-propyl-trans-decahydronaphthalene, 6-(1,6,7-trifluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,6,7-trifluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,6,7-trifluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,6,7-trifluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,2,3,8-tetrafluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6- (1-f luoro-2-trif luoromethoxynaphthalen-6-yl) -2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-ethyl-tran s-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-trifluoromethoxy-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-7-trifluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-5-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-trifluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-2 -difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-difluoromethoxy-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-7-difluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6- (1, 8-dif luoro-2-dif luoromethoxynaphthalen-6-yl) -2-butyl-` CA 02510394 1999-08-23 trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,8-difluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-difluoromethoxynaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6- (1-f luoro-2-chloronaphthalen-6-yl) -2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yi)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-2-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-y1)-2-ethyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-chloro-3-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6- (2-chloro-1, 3-dif luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6- (2-chloro-1, 3-dif luoronaphthalen-6-yl) -2-pentyl-trans-decahydronaphthalene, 6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-chloro-1,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene;

6-(1-fluoro-7-chloronaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-y1)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-7-chloronaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6- (1, 6-difluoro-7-chloronaphthalen-3-yl) -2-ethyl-trans-decahydronaphthalene, 6- (1, 6-dif luoro-7-chloronaphthalen-3-yl) -2-propyl-trans-decahydronaphthalene, 6- (1, 6-dif luoro-7-chloronaphthalen-3-yl) -2-butyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-chloronaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6- (1, 6-dif luoro-7-chloronaphthalen-3-yl) -2-hexyl-trans-decahydronaphthalene, 6- (1, 6-dif luoro-7-chloronaphthalen-3-yl) -2-heptyl-trans-decahydronaphthalene, 6- (1, 3, 8-trif luoro-7-chloronaphthalen-6-yl) -2-methyl-trans-decahydronaphthalene, 6- (1, 3, 8-trif luoro-7-chloronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-chloronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthale ne, 6-(2-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-cyano-l-fluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-cyano-3-fluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6- (2-cyano-3-f luoronaphthalen-6-yl) -2-heptyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-methyl-trans=
decahydronaphthalene, 6- (2-cyano-1, 3-dif luoronaphthalen-6-yl) -2-ethyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(2-cyano-1,3-difluoronaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-y1)-2-butyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6- (1-f luoro-7-cyanonaphthalen-3-yl) -2-hexyl-trans-decahydronaphthalene, 6-(1-fluoro-7-cyanonaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,8-difluoro-7-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-methyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-pentyl-trans-decahydronaphthalene, 6- (1, 6-dif luoro-7-cyanonaphthalen-3-yl) -2-hexyl-trans-decahydronaphthalene, 6-(1,6-difluoro-7-cyanonaphthalen-3-yl)-2-heptyl-trans-decahydronaphthalene, 6- (1, 3, 8-trif luoro-7-cyanonaphthalen-6-yl) -2-methyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-ethyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-propyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-butyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-pentyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-hexyl-trans-decahydronaphthalene, 6-(1,3,8-trifluoro-7-cyanonaphthalen-6-yl)-2-heptyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[3-fluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1,3-difluoro-2-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-methyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-ethyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-propyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-butyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1-fluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-propyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1,8-difluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-methyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-ethyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-propyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-butyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1,6-difluoro-7-(trifluoromethyl)naphthalen-3-yl]-2-heptyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-methyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-ethyl-trans-decahydronaphthalene, 6- [1, 3, 8-trifluoro-7- (trifluoromethyl) naphthalen-6-yl] -2-propyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-butyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-pentyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-hexyl-trans-decahydronaphthalene, 6-[1,3,8-trifluoro-7-(trifluoromethyl)naphthalen-6-yl]-2-heptyl-trans-decahydronaphthalene, methyl-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylatel, methyl-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, _ 212 methyl-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)n.aphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1-fluoro-7-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-7-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2-difluoro-7-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1-fluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,8-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,8-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,6-difluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,6-difluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,3,8-trifluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,3,8-trifluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 3-fluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-fluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-fluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-f luoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-f luoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-fluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 3-fluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-6-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-ethyl-trans=decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,7-difluoro-6-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-2-carboxylate, methyl 1,2-difluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-butyl-trans-decahydronaphthalen-2 -yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-hexyl-trans-decahydronaphthalen-2 -yl)naphthalene-7-carboxylate, methyl 1,2-difluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1,2,8-trifluoro-3-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-7-carboxylate, methyl 1-fluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1-fluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-propyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-butyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-pentyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,7-difluoro-2-(6-heptyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-methyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-ethyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-propyl-trans-decahydronaphthalen-2 -y1)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-butyl-trans-decahydronaphthalen-2 -yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-pentyl-trans-decahydronaphthalen-2 -yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-6-carboxylate, methyl 1,8-difluoro-2-(6-heptyl-trans-decahydronaphthalen-2 -yl)naphthalene-6-carboxylate, methyl 1,2,8-trifluoro-7-(6-methyl-trans-decahydronaphthal en-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-ethyl-trans-decahydronaphthale n-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-propyl-trans-decahydronaphthal en-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-butyl-trans-decahydronaphthale n-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-pentyl-trans-decahydronaphthal en-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-hexyl-trans-decahydronaphthalen-2-yl)naphthalene-3-carboxylate, methyl 1,2,8-trifluoro-7-(6-heptyl-trans-decahydronaphtha 1 en-2-yl)naphthalene-3-carboxylate.

Example 21: Synthesis of 2,6-bis(3-butenyl)-trans-decahydronaphthalene (1-22) O HCOOH O 1) Ph3P=CHOCfi3 CO O' 0 2> FiC1 0 3) NaOH O
1) Ph3O Ph3P=Chl2 2) hlCO
3} 4) HCI

(21-a) Synthesis of trans-decahydronaphthalen-2,6-dione 21 g of trans-decahydronaphthalen-2,6-dione monoethyleneacetal was dissolved in 110 ml of toluene. 50 ml of formic acid was added to the solution, and the mixture was stirred for 1 hour at room temperature. Water was added to the mixture, and the organic phase was separated, rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated to obtain 16 g of pale yellow solid trans-decahydronaphthalen-2,6-dione.

(21-b) Synthesis of trans-decahydronaphthalene-2,6-dicarbaldehyde An 80 ml THF solution of 16 g of trans-decahydronaphthalen-2,6-dione, which was obtained in (21-a), was added dropwise to a Wittig reagent prepared from 72 g of methoxymethyltriphenylphosphonium chloride and 26 g of potassium t-butoxide in 290 ml of THF, while the mixture was cooled to 10 C or lower. The temperature was reduced to room temperature. After the mixture was stirred for 4 hours, water and hexane were added. The organic phase was separated and rinsed with water, and the solvent was evaporated. The pale yellow oily substance obtained was dissolved in 90 ml of THF.

90 ml of 10% hydrochloric acid was added to the solution, and the mixture was heated for 3 hours under refluxing. The temperature was reduced to room temperature, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate. Organic phases were combined, and rinsed with a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence. Then, the solvent was evaporated. The pale yellow solid substance obtained was dissolved in 85 ml of methanol. 10 ml of 10%
aqueous solution of sodium hydroxide was added to the solution while the mixture was cooled to 10 C or lower. After the mixture was stirred for 2.5 hours at room temperature, the temperature was reduced to room temperature. Then, the solvent was evaporated, and the pale yellow solid substance obtained was rinsed with water and recrystallized from a hexane solution to obtain 16 g of white solid trans-decahydronaphthalene-2,6-dicarbaldehyde.
(21-c) Synthesis of 2, 6-bis (3-oxopropyl) -trans-decahydronaphthalene Reaction of 16 g of trans-decahydronaphthalene-2,6-dicarbaldehyde, which was obtained in (21-a), with a Wittig reagent which is similar to that used in (1-b) was repeated twice to obtain 15 g of pale yellow solid 2, 6-bis (3-oxopropyl)-trans-decahydronaphthalene.
(21-d) Synthesis of 2, 6-bis (3-butenyl) -trans-decahydronaphthalene An 85 ml THF solution of 15 g of 2,6-bis(3-oxopropyl)-trans-decahydronaphthalene, which was obtained in (21-c), was added dropwise to a Wittig reagent prepared from 60 g of methyltriphenylphosphonium iodide and 18 g of potassium t-butoxide in 300 ml of THF, while the mixture was cooled to 10 C or lower. The temperature was reduced to room temperature. After the mixture was stirred for 4 hours, water and hexane were added. The organic phase was separated and rinsed with water, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane) to obtain 6 g of 2,6-bis(3-butenyl)-trans-decahydronaphthalene (1-22) a colorless oily substance.

The following compounds were prepared in the same manner as mentioned above:

2,6-bis(3-pentenyl)-trans-decahydronaphthalene, 2,6-bis(1-pentenyl)-trans-decahydronaphthalene, 2,6-bis(1-propenyl)-trans-decahydronaphthalene, 2,6-divinyl-trans-decahydronaphthalene.

Example 22: Synthesis of 2-(trans-4-propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene (1-23) 22?!.
O 1) Ph3P=CHOCH3 Ph3P=CH2 _Oa_o~
2) HCI-_ , O --~
3) NaOH

r-C

(22-a) Synthesis of 6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde Reaction of 28 g of 6-(trans-4-propylcyclohexyl)-tran s-decahydro-2-naphthalenone with the Wittig reagent described above was carried out to obtain 28 g of white solid 6-(tra ns-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldeh yde.
(22-b) Synthesis of 2- (trans -4 -propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene Reaction of 28 g of 6-(trans-4-propylcyclohexyl)-tran s-decahydronaphthalene-2-carbaldehyde, which was obtained in (22-a), with a Wittig reagent which is similar to that used in (1-d) was carried out to obtain 10 g of white solid 2-(tra ns-4-propylcyclohexyl)-6-vinyl-trans-decahydronaphthalene (I-4).

The following compound was prepared in the same manne r as mentioned above:

2-(trans-4-propylcyclohexyl)-6-(3-butenyl)-trans-decahydronaphthalene.

Example 23: Synthesis of 2-(trans-4-propylcyclohexyl)-6-(trans-l-propenyl)-trans-decahydronaphthalene (1-24) 1) Ph3P=CHCH3 0 2) PhSOZH
17 ' 225.
Reaction of 12 g of 6-(trans-4-propylcyclohexyl)-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in (22-a), with the Wittig reagent described above, and treatment with benzenesulfinic acid were carried out to obtain 4 g of white solid 2-(trans-4-propylcyclohexyl)-6-(trans-l-propenyl)-trans-decahydronaphthalene (1-24).

The following compounds were prepared in the same manner as mentioned above:

2-(trans-4-propylcyclohexyl)-6-(trans-l-pentenyl)-trans-decahydronaphthalene, 2-(trans-4-propylcyclohexyl)-6-(trans-3-pentenyl)-trans-decahydronaphthalene.

Example 24: Synthesis of 2-(trans-4-propylcyclohexyl)-6-(2,2-difluoroethenyl)-trans-decahydronaphthalene (I-25) C12FCCOONa, PPh O
F
To a solution of 8.7 g of 6-(trans-4-propylcyclohexyl)decahydronaphthalene-2-carbaldehyde, which was obtained in (22-a), and 8.7 g of triphenylphosphine in 10 ml of diethyleneglycol dimethylether (Diglyme), the solution being heated at 160 C while stirring, a 20 ml Diglyme solution of 7.1 g of sodium chlorodifluoroacetate was added dropwise over a period of 30 minutes. After the heating was continued under the same conditions for 2 hours, the mixture was left to cool to room temperature. Water and hexane were added to the mixture, and the organic phase was separated, rinsed with 10%

hydrochloric acid, a saturated aqueous solution of sodium carbonate, and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane) and recrystallized from ethanol at C or lower to obtain 0.6 g of 2-(trans-4-propylcyclohexyl)-6-(2,2-difluoroethenyl)-trans-decahydronaphthalene (1-25).
Example 25: Synthesis of trans-6-propyl-2-[4-(4-10 methyiphenyl)ethynylphenyl]-trans-decahydronaphthalene C3Hi HCC--((~~--CH3 (..3H7 O ~ Pd(PPh~4~/ O C=C-(( )}-CH3 23 g of trans-6-propyl-2-(4-iodophenyl)-trans-decahydronaphthalene was dissolved in 45 ml of DMF. 1.3 g of tetrakis(triphenylphosphine)palladium(0), 0.4 g of copper iodide (I), and 6.0 g of (4-methyl)phenylacetylene were added to the mixture. After heating the mixture for 2 hours at 50 C
while stirring, the mixture was cooled to room temperature, and 10% hydrochloric acid was added to the mixture. After extraction was carried out using toluene, the organic phase was rinsed with a saline solution and dried on anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane) and recrystallized once from ethanol to obtain 10 g white crystals of trans-6-propyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene.

The following compounds were prepared in the same manner as mentioned above:

trans-6-methyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[3-fluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynyiphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[3,5-difluoro-4-(4-methyiphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[3,5-difluoro-4-(4-methylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans- 6-pentyl-2- [4- (4-ethylphenyl) ethynylphenyl] -trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-ethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-propyiphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-propylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-methoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-allyloxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-[4-(3-butenyl)phenyl]ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-fluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(3,4-difluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenylJ-trans-decahydronaphthalene, trans-6-propyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(3,4,5-trifluorophenyl)ethynylphenylJ-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl] -trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-trifluoromethoxyphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-trifluoromethylphenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-methyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-ethyl-2-[4-(4-chiorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-propyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-butyl-2- [4- (4-chlorophenyl) ethynylphenyl] -trans-decahydronaphthalene, trans-6-pentyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-hexyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene, trans-6-heptyl-2-[4-(4-chlorophenyl)ethynylphenyl]-trans-decahydronaphthalene.

Example 26: Synthesis of trans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene C3H 1) Ph3P=CHOCH3~H Oa MgBr TSOH H2, Pd-C
2) HCI ~-(F
(HOhB-(( )) h / HIO4 ~-( C,H C.3H i i Pd(PPh3)4 F
O O
C3H 1) BuLi 1)SOG2 POCI3 10 2) C 2(9) 2) NH3(9) F
F
C, O O CN

F

(26-a) Synthesis of trans-6-propyl-2-(2-oxoethyl)-trans-decahydronaphthalene Reaction of 10 g of trans-6-propyl-trans-decahydronaphthalene-2-carbaldehyde, which was obtained in (12-a), with a Wittig reagent which is similar to that used in (12-a) was carried out to obtain 9 g of white solid trans-6-propyl-~-(2-oxoethyl)-trans-decahydronaphthalene.
(26-b) Synthesis of trans- 6-propyl-2- (2-phenylethyl) -trans-decahydronaphthalene Reaction of 9 g of trans-6-propyl-2-(2-oxoethyl)-trans-decahydronaphthalene, which was obtained in (26-a), with a Grignard reagent similar to that used in Example 2 was carried out to obtain 11 g of white solid trans-6-propyl-2-(2-phenylethyl)-trans-decahydronaphthalene.

(26-c) Synthesis of trans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene 11 g of trans-6-propyl-2-(2-phenylethyl)-trans-decahydronaphthalene, which was obtained in (26-b), was iodized in a manner similar to that in (1-a) to obtain 13 g of pale yellow solid trans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene.

(26-d) Synthesis of trans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene Coupling reaction of 13 g of trans-6-propyl-2-[2-(4-iodophenyl)ethyl]-trans-decahydronaphthalene, which was obtained in (26-c), was carried out in a manner similar to that in (1-b) to obtain 7 g of white solid trans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene.

(26-e) Synthesis of trans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene 20 ml of a 1.5 M hexane solution of n-butyl lithium was added dropwise to a 35 ml THF solution of 7 g of trans-6-propyl-2-[2-[4-(3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene, which was obtained in (26-d), while cooling the solution to -78 C. After stirring for 10 minutes, carbon dioxide was injected into the mixture until saturation.

After the mixture was left to stand until the temperature reached room temperature, 10% hydrochloric acid was added.
The organic phase was extracted using ethyl acetate, rinsed with water, and dried on anhydrous magnesium sulfate. Then, the solvent was evaporated. The pale yellow solid substance obtained was suspended in 60 ml of 1,2-dichloroethane. 2 g of thionyl chloride, 0.1 ml of pyridine, and 1 ml of DMF were added to the suspension, and the mixture was stirred for 1 hour at room temperature. The solvent was evaporated, and the yellow oily substance obtained was dissolved in 150 ml of dichloromethane.. Ammonia gas was injected into the solution while cooling the solution to 10 C or lower until saturation.
After stirring for 1 hour at room temperature, the solvent was evaporated. The yellowish brown solid substance obtained was suspended in 50 ml of DMF. 2 ml of phosphorus oxychloride was added to the suspension while cooling the suspension to 10 C
or lower, and the mixture was stirred for 3 hour at room temperature. Water was added to the mixture. The organic phase was extracted using toluene, rinsed with a saturated saline solution, and dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane), and recrystallized from ethanol to obtain 1 g of white solid trans-6-propyl-2-[2-[4-(4-cyano-3,5-difluorophenyl)phenyl]ethyl]-trans-decahydronaphthalene.

Example 27: Synthesis of trans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene CHZ=CH O HBr (CF3SO2)20 CH2=CH(CH2)2MgBr OCH3 -~- P~d NiBr2( dppe?2"
CH2=CH
O (CHZ)z-CH=CHz Trans-6-(4-methoxyphenyl)-trans-2-vinyldecahydronaphthalene obtained in a manner similar to that in Example 1 was dissolved in glacial acetic acid. A 47%
aqueous solution of hydrobromic acid was added to the solution, and the mixture was heated for 20 hours under refluxing. The mixture was cooled to room temperature, and water was added to the mixture. Extraction was carried out using toluene, and the organic phase was rinsed with water and then dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The oily substance obtained, which was trans-6-(4-hydroxyphenyl)-trans-2-vinyldecahydronaphthalene, was dissolved in methylene chloride. Trifluoromethanesulfonic anhydride was added dropwise to the solution while cooling the mixture at 10 C or lower. Subsequently, pyridine was added dropwise, and the mixture was stirred for 1 hour. Water was added, and the mixture was left to stand until the temperature reached room temperature. Then, extraction was carried out using ethyl acetate, and the organic phase was rinsed with water and then dried on anhydrous sodium sulfate. Then, the solvent was evaporated. The oily substance obtained, which was trifluoromethanesulfonate, was dissolved in THF.

Dibromobis(diphenylphosphinoethane)nickel(II) and triphenylphosphine were added to the solution. A Grignard reagent prepared from 3-butenyl bromide (1-bromo-3-butene) was added dropwise to the mixture, and the mixture was heated for 16 hours under refluxing. The mixture was left to stand until the temperature reached room temperature. Then, 10%

hydrochloric acid was added to the mixture, and the organic phase was extracted using ethyl acetate, rinsed with water, and dried on anhydrous sodium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane) and recrystallized (ethanol) to obtain white solid trans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene.
The following compounds were prepared in the same manner as mentioned above:

trans-6-[4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene, trans-6-(4-methylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-ethylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-propylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-methylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-ethyl-3-fluorophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3-fluoro-4-propylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-methylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-vinyldecahydronaphthalene, trans-6-[3,5-difluoro-4-(3-butenyl)phenyl]-trans-2-vinyldecahydronaphthalene, trans-6-(4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-ethylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[4-(3-butenyl)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-ethyl-3-fluorophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3-fluoro-4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-methylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[3,5-difluoro-4-(3-butenyl)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-methylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-ethylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-[4-(3-butenyl)phenyl]-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-methylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-ethyl-3-fluorophenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3-fluoro-4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-[4-(3-butenyl)-3-fluorophenyl]-trans-2-(3-butenyl)decahydronaphthalene, trans-6- (3, 5-dif luoro-4-methylphenyl) -trans-2- (3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-ethylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(3,5-difluoro-4-propylphenyl)-trans-2-(3-butenyl)decahydronaphthalene, trans-6-[3,5-difluoro-4-(3-but*enyl)phenyl]-trans-2-(3-butenyl)decahydronaphthalene, trans-6-(4-cyanophenyl)-trans-2-vinyldecahydronaphthalene, trans-6-(4-cyanophenyl)-trans-2-(1-propenyl)decahydronaphthalene, trans-6-(4-cyanophenyl)-trans-2-(3-butenyl)decahydronaphthalene.
Example 28: Synthesis of trans-6-[4-(2-propenyloxy)phenyl trans-2-vinyldecahydronaphthalene CH2=CH ~ 1) NaH
OH2) CHz-CHCFTyBr CH2=CH
OCHZCH=CH2 A THF solution of trans-6-(4-hydroxyphenyl)-trans-2-vinyldecahydronaphthalene obtained by the method disclosed in Example 7 was added dropwise to a suspension of sodium hydroxide in THF, the suspension being cooled to 10 C or lower. After stirring for 30 minutes at room temperature, a THF solution of 2-propenyl bromide (1-bromo-2-propene) was added dropwise, and the mixture was heated for 1 hour under refluxing. The mixture was left to stand until the temperature reached room temperature, and extraction was carried out using toluene. The organic phase was rinsed with a saturated saline solution and then dried on anhydrous sodium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane) and recrystallized (ethanol) to obtain white solid trans-6-[4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene.
The following compounds were prepared in the same manner as mentioned above:

trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene, trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene, trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-vinyldecahydronaphthalene, trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-vinyidecahydronaphthalene, trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-vinyldecahydronaphthalene, trans-6-[4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-propenyl) decahydronaphthalene, trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-(1-propenyl)decahydronaphthalene, trans-6-[4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene, trans-6-[4-(trans-2-butenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene, trans-6-[3-fluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene, trans-6-[4-(trans-2-butenyloxy)-3-fluorophenyl]-trans-2-(1-butenyl)decahydronaphthalene, trans-6-[3,5-difluoro-4-(2-propenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene, trans-6-[3,5-difluoro-4-(trans-2-butenyloxy)phenyl]-trans-2-(1-butenyl)decahydronaphthalene.

Example 29: Synthesis of trans-2-[3-fluoro-4-(2-propenyloxycarbonyl)phenyl]-trans-6-vinyldecahydronaphthalene F
CH2=CH O CHZ=CHCH2OH
COOH pCC,DMAO' F
CH2=CH
COOCH2CH=CH2 Trans-2-(4-carboxy-3-fluorophenyl)-trans-6-vinyldecahydronaphthalene obtained in a manner similar to that in Example 6, dicyclohexylcarbodiimide, and N,N-dimethyl-4-aminopyridine were dissolved in methylene chloride. To this solution, a methylene chloride solution of 2-propenol was added dropwise. After the mixture was stirred for 20 hours at room temperature, the mixture was filtered, and solvent was evaporated. Thereafter, the residue was purified by silica gel column chromatography (hexane) and recrystallized (ethanol) to obtain white solid trans-2-[3-fluoro-4-(2-propenyloxycarbonyl)phenyl]-trans-6-vinyldecahydronaphthalene Example 30: Synthesis of 2-[6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene (1-26) Brn+g 00 OCH, TsOHs O H2 'BuOK
Q - --T - -- ---i O OC% Pd-C

HBr TfzO
O O OCFi3~~ O O OH Pyridine Br-N, OTf (30-a) Synthesis of 2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene In a manner similar to that in (1-a), reaction of 24 g of 6-propyldecahydro-2-naphthalenone with a Grignard reagent prepared from 6-methoxy-2-bromonaphthalene and dehydration were carried out to obtain 32 g of pale yellow liquid 2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene.
(30-b) Synthesis of 2- (6-methoxynaphthalen-2-yl) -trans-6-propyl-trans-decahydronaphthalene In a manner similar to that in (1-e), catalytic hydrogenation reduction and isomerization of 32 g of 2-(6-methoxynaphthalen-2-yl)-trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene, which was obtained in (30-a), were carried out to obtain 30 g of 2-(6-methoxynaphthalen-2-yi)-trans-6-propyl-trans-decahydronaphthalene as a pale yellow oily substance..
(30-c) Synthesis of 6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol 30 g of trans-2-propyl-trans-6-(3-fluoro-4-methoxyphenyl)-trans-decahydronaphthalene, which was obtained in (30-b), was dissolved in a mixture of 150 ml of glacial acetic acid and 150 ml of 48% hydrobromic acid, and the solution was heated for 8 hours under refluxing. The solution was cooled to room temperature. Water and ethyl acetate were added to the solution. After the organic phase was separated, the organic phase was rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 24 g yellow crystals of 6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol.
(30-d) Synthesis of 2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene A 120 ml dichloromethane solution of 25 g of trifluoromethanesulfonic anhydride was added dropwise to a 100 ml dichloromethane solution of 24 g yellow crystals of 6-(trans-6-propyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl)-2-naphthol, which were obtained in (30-c), while the solution was cooled at 0 . Subsequently, a 70 ml dichloromethane solution of 14 g of pyridine was added dropwise. After the mixture was stirred for 1 hour at room temperature, 10% hydrochloric acid was added, and the organic phase was separated and rinsed with water, a saturated aqueous solution of sodium hydrogencarbonate, water, and a saturated saline solution, in sequence, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane) to obtain 25 g of white solid 2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene.

(30-e) Synthesis of 2-(6-(3-butenyl)naphthalen-2-yl)-6-propyl-trans-decahydronaphthalene A Grignard reagent prepared from 1.5 g of metal magnesium and 9 g of 4-bromo-l-butene was added dropwise to a 130 ml THF
solution of 25 g of 2-(6-trifluoromethanesulfonyloxynaphthalen-2-yl)-trans-6-propyl-trans-decahydronaphthalene, which was obtained in (30-d), and 0.8 g of dichlorobis(diphenylphosphinoethane)nickel(II), the solution being cooled to 10 C or lower. The temperature was reduced to room temperature, and the mixture was stirred for 6 hours. After 10o hydrochloric acid was added, the organic phase was separated, rinsed with water and a saturated saline solution, in sequence, and dried on anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane) and recrystallized from ethanol to obtain 3 g white crystals of 2-[6-(3-butenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene The following compounds were prepared in the same manner as mentioned above:

2-[6-(3-butenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene, 2-[6-(3-butenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene, 2-[6-(3-butenyl)naphthalen-2-yl)-6-butyl-trans-decahydronaphthalene, 2-[6-(3-butenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene, 2-[6-(3-butenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene, 2-[6-(3-butenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-ethyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-propyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-butyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-pentyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-hexyl-trans-decahydronaphthalene, 2-[6-(trans-3-pentenyl)naphthalen-2-yl]-6-heptyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-methyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-ethyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-propyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-butyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-pentyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-hexyl-trans-decahydronaphthalene, 2-(6-methoxynaphthalen-2-yl)-6-heptyl-trans-decahydronaphthalene, 2-[6-(2-propenyloxy)naphthalen-2-yl]-6-methyl-trans-decahydronaphthalene, 2-[6-(2-propenyloxy)naphthalen-2-yl]-6-,ethyl-trans-DETNL-ki~DES OU BREVETS VOLL~~~~INEUX
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Claims (7)

CLAIMS:

1. A compound represented by general formula (II):
wherein, R4 represents an alkyl group, alkoxy group, alkenyl group, alkenyloxy group or alkoxyalkyl group, L1 represents -CH2CH2-, -CH(CH3)CH2-, -CH2CH(CH3)-, -CH2O-, -OCH2-, -CF20-, -OCF2-, -COO-, -OCO-, -CH=CH-, -CF=CF-, -C=C-, -O(CH2)3-, -(CH2) 3O-, -(CH2)4- or a single bond, wherein R4 represents an alkenyl group, alkenyloxy group or alkoxyalkyl group when L1 represents a single bond, ring A represents a trans-1, 4-cyclohexylene group in which one CH2 group or more than one non-adjacent CH2 groups in the group is optionally replaced by -O- or -S-, a 1,4-phenylene group in which one CH2 group or more than one non-adjacent CH2 groups in the group is optionally replaced by -N=, a 1,4-cyclohexenylene group, a 1,4-bicyclo(2,2,2)octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a trans-decahydronaphthalene-trans-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and is optionally substituted with a cyano group or halogen, m represents an integer of 1 or 2, and the decahydronaphthalene ring has a trans form.

2. A production method of general formula (II) as defined in claim 1 comprising: reducing a compound represented by general formula (II-A) :

wherein, R4 is the same as previously defined in claim 1, ring E represents a 1,4-phenylene group or trans-1,4-cyclohexylene group, L1 and m are the same as previously defined in claim 1, and the decahydronaphthalene ring has a trans form, and oxidizing the hydroxyl group as necessary.

3. A compound represented by general formula (V-2):
wherein, U1 and U2 independently represent an oxygen atom or the following structure:

wherein, k represents an integer from 1 to 7, L1 is the same as previously defined in claim 1, and the decahydronaphthalene ring has a trans form.

4. A production method of general formula (V-2) as defined in claim 3 or general formula (V-1):

wherein U1 and U2 independently represent an oxygen atom or the following structure:

wherein, k represents an integer from 1 to 7, L1 is the same as previously defined in claim 1, and the decahydronaphthalene ring has a trans form the method comprising: reacting a compound represented by general formula (V-1A) or general formula (V-2A):
wherein, k is the same as previously defined in claim 3, and L1 is the same as previously defined in claim 1 with a secondary amine to form an enamine, and reacting said enamine with methyl vinyl ketone to obtain a compound represented by general formula (V-1B) or general formula (V-2B) :

wherein, k is the same as previously defined in claim 3, and L1 is the same as previously defined in claim 1 followed by reductive hydrogenation.

5. A production method of general formula (V-l) as defined in claim 4 comprising: reducing a compound represented by formula (V-lC) by hydrogenation in the presence of metal catalyst:

oxidizing the hydroxyl groups, and protecting the carbonyl groups when both U1 and U2 of claim 3 are not an oxygen atom.

6. A production method of general formula (V-2) as defined in claim 3 comprising: reducing a compound represented by general formula (V-2C) wherein, L1 is the same as previously defined in claim 1, ring G represents a cyclohexane ring or benzene ring, a single bond(s) of the cyclohexane ring is optionally replaced by double bond(s), and rings F and H respectively and independently represent the following structures:

wherein, U1 is the same as previously defined in claim 3 or 4, a single bond(s) of the cyclohexane ring is optionally replaced by double bond(s), oxidizing the hydroxyl group, and further protecting the carbonyl group when both U1 and U2 of claim 3 are not an oxygen atom.

7. A production method of general formula (V-la):

wherein, k is the same as previously defined in claim 3 or 4, comprising monoacetalation of a compound represented by general formula (V-lD):