JP2001019648A - Tetrahydronaphthalene derivative and liquid crystal composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide the subject new compound that has a tetrahydronaphthalene ring, shows liquid crystal properties and is useful as an electrooptical liquid crystal display material. SOLUTION: This new compound is represented by formula I [R is a (substituted) alkyl or the like; m and n are 0 or 1; rings A through C are each trans-1,4-cyclohexylene or the like; L, M, Q are each -CH2CH2- or the like or a single bond; X1 through X3 are each H, fluorine; Z is H or a halogen, a (fluorinated) alkyl or the like], typically 2-propyl-6-(3,4-difluorophenyl)-1,2,3,4- tetrahydronaphthalene. The compound of formula I is prepared by effecting the dehydrocondensation reaction between a compound of formula II and pyrrolidine, allowing the product to react with methyl vinyl ketone, oxidizing the resultant compound of formula III, allowing the oxidation product to react with trifluoromethanesulfonic anhydride or the like and allowing the resultant triflate to react with a Grignard reagent prepared from a compound of formula IV (X is a halogen) and magnesium in the presence of a transition metal catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel liquid crystalline compound which is a tetrahydronaphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing the same, and a liquid crystal display device using the same.

[0002]

2. Description of the Related Art Liquid crystal display elements have been used in various measuring instruments such as watches and calculators, panels for automobiles, word processors, electronic organizers, printers, computers, televisions and the like. Typical liquid crystal display systems are TN (twisted nematic) type, STN (super twisted nematic) type, DS (dynamic light scattering) type, GH (guest / host) type or FLC capable of high-speed response. (Ferroelectric liquid crystal). As a driving method, a multiplex driving has been generally used instead of the conventional static driving, and a simple matrix method, more recently, an active matrix method has been put to practical use.

As the liquid crystal material used for these, a great variety of liquid crystal compounds have been synthesized so far, and these are used according to the display system, the driving system, or the application. However, improvement of the performance of liquid crystal display elements (improvement of display quality, enlargement of display screen, etc.)
Is increasing year by year, and new liquid crystal compounds are being developed to satisfy the demand.
The liquid crystal compound is composed of a central skeleton portion usually called a core and terminal portions on both sides. Usually, the ring structure constituting the core portion of the liquid crystal compound includes a 1,4-phenylene group (which may be substituted with one or two halogen atoms, a cyano group, a methyl group, or the like) and trans-1,4 −
Cyclohexylene groups make up the majority. However, liquid crystal compounds composed only of 1,4-phenylene groups and trans-1,4-cyclohexylene groups are limited in their types and characteristics, and cannot satisfy the above requirements by themselves. It is a fact. Examples of the ring structure other than the 1,4-phenylene group and the trans-1,4-cyclohexylene group include a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, and a 1,3-dioxane-trans- Heterocyclic systems such as 2,5-diyl group, transdecalin-2,6-diyl group, naphthalene-2,6
-Fused ring systems such as -diyl group, tetrahydronaphthalene-2,6-diyl group, bicyclo [2,2,2] octane-1,4-diyl group, spiro [3,3] heptane-2,6-diyl group At present, only a few are practically used due to problems in manufacturing (technology, cost, etc.) and stability.

In these condensed ring systems, the tetrahydronaphthalene-2,6-diyl group has properties other than its liquid crystallinity (phase transition temperature), especially nematic liquid crystal, although it has been reported for a long time. Little is known about its properties. (As a smectic liquid crystal,
It has been reported that optically active alcohol esters of tetrahydronaphthalenecarboxylic acid exhibit interesting properties as ferroelectric liquid crystals. In general, in a liquid crystal compound, at least one of the terminal portions is a chain (side chain) group, and in the case of a so-called p-type liquid crystal having a positive dielectric anisotropy, the other is often a polar group.

In order to reduce the driving voltage in the TN or STN display system, a so-called strong p-type (positive and large dielectric anisotropy) compound is required. For such a purpose, a compound having a cyano group at the molecular terminal and further containing one or more fluorine atoms in the same direction of the molecule is usually used. Most of the currently reported tetrahydronaphthalene derivatives are so-called n-type liquid crystals having a dielectric anisotropy of 0 to negative, and a slight phenyltetrahydronaphthalene skeleton is used as a p-type liquid crystal in which a polar group is introduced in the molecular long axis direction. Only the compound (Helv. Chim. Act.
a 65 1318 (1982)-Reference (a))
It does not describe electro-optical characteristics or application examples.

As the P-type compound to be used in the above-mentioned active matrix driving method, a compound having only a fluorine atom, a fluoroalkoxyl group or a fluoroalkyl group as a polar group is used. There is no.

In addition, liquid crystal compounds which are tetrahydronaphthalene derivatives generally have poor compatibility with other liquid crystal compounds in many cases. For improvement, it is considered effective to introduce a lateral substituent (preferably a fluorine atom) into the naphthalene skeleton. In the use in the active matrix system, substitution with a fluorine atom is considered to be effective even when a polar group is directly introduced into a tetrahydronaphthalene ring. There is no example of such a fluorotetrahydronaphthalene derivative actually synthesized, and in fact, it is impossible to estimate what characteristic values such a compound has. Similarly, a compound having a structure in which a fluoroalkoxyl group or a fluoroalkyl group is directly bonded as a polar group is not known.

Further, in a liquid crystal compound, by introducing an alkenyl group in place of an alkyl group usually used as a side chain, improvement in liquid crystallinity, reduction in viscosity,
It is known that excellent effects such as improvement of steepness in display characteristics can be obtained. However, these alkenyl groups are usually introduced in a form directly linked to a cyclohexane ring, and have not been reported as tetrahydronaphthalene derivatives.

Similarly, no tetrahydronaphthalene derivative having an alkoxylalkyl group, fluoroalkyl group, fluoroalkenyl group, fluoroalkenyloxy group or the like as a side chain has been reported.

In the liquid crystal compound, a linking group having a ring structure in the core may be a single bond or an ethylene group (—CH ₂ CH
Many divalent organic groups other than _2- ) are known.

For example, it is known that a liquid crystal compound having a tetramethylene group or a propylene group has a lower melting point and better compatibility with other liquid crystal compounds than a liquid crystal compound having a corresponding single bond or an ethylene group. ing. However, a liquid crystalline compound having a tetramethylene group or a propylene group as a tetrahydronaphthalene derivative is not known. Also, a difluorooxymethylene group (—CF ₂ O
-, - OCF ₂ -) and difluoro ethenyl group (-CF =
It has been reported that a liquid crystal compound having CF-) has a small viscosity and is effective in increasing the response speed, but is not known as a tetrahydronaphthalene derivative.

[0012]

An object of the present invention is to provide a novel liquid crystalline compound having a tetrahydronaphthalene ring, and to provide a practical liquid crystal composition using the compound. It is in.

[0013]

The present invention has been made in order to solve the above problems. General formula (I)

[0014]

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(In the formula, R represents an alkyl group having 1 to 20 carbon atoms, an alkoxyl group, an alkenyl group or an alkenyloxy group. These are represented by an alkoxyl group having 1 to 7 carbon atoms or 1 to 7 halogen atoms. M and n are each independently 0 or 1, and rings A, B and C are each independently trans-1,
4-cyclohexylene group, or 1,4-phenylene group, pyridine-2,5-diyl group, pyrimidine-2,5 which may be substituted by one or more halogen atoms
-Diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diyl group, trans-1,3-dioxane-
2,5-diyl group, transdecahydronaphthalene-
2,6-diyl group, tetrahydronaphthalene-2,6-
L represents a diyl group or a naphthalene-2,6-diyl group;
M and Q are each independently —CH ₂ CH ₂ —, —CH _{2
CH 2 CH 2 CH 2 -,} - CH = CH -, - CH = CHC
_{H 2 CH 2 -, - CH} 2 CH 2 CH = CH -, - CH (CH
_{3) CH 2 -, - CH} 2 CH (CH 3) -, - CF = CF
_{-, - CH 2 O -,} - OCH 2 -, - CF 2 O -, - OC
F ₂ —, —COO—, —OCO—, —C≡C— or a single bond; X ¹ , X ² and X ³ each independently represent a hydrogen atom or a fluorine atom; An atom, a cyano group, a cyanato group, or a group having 1 or more carbon atoms which may be substituted by one or more fluorine atoms.
20 represents an alkyl group, an alkoxyl group, an alkenyl group, or an alkenyloxy group.

However, when m = 0 and R represents an unsubstituted alkyl group or alkoxyl group, 1) at least one of X ¹ , X ² and X ³ represents a fluorine atom, and / or 2) A 1,4-phenylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5 in which at least one of the ring B or the ring C is substituted by one or more halogen atoms A diyl group, pyridazine-3,
6-diyl group, trans-1,3-dioxane-2,5
-Diyl group, transdecahydronaphthalene-2,6-
Represents a diyl group, a tetrahydronaphthalene-2,6-diyl group, a naphthalene-2,6-diyl group, and / or 3) alkyl having 1 to 20 carbon atoms wherein Z is substituted by one or more halogen atoms. group, an alkoxyl group, an alkenyl group, an alkenyloxy group, and / or 4) ₂ Q is -CH when _{n = 0 CH 2 -, -} CF = CF
—, —CF ₂ O—, —OCF ₂ —, —C≡C— and / or 5) When n = 1, at least one of M and Q represents a single bond. A) a tetrahydronaphthalene derivative represented by the formula:

2. 2. The tetrahydronaphthalene derivative according to the above 1, wherein m = 1 in the general formula (I). 3. ^2. The tetrahydronaphthalene derivative according to the above 1, wherein in the general formula (I), at least one of X ¹ , X ² and X ³ is a fluorine atom. 4. 4. The tetrahydronaphthalene derivative according to the above 3, wherein in the general formula (I), at least one of X ¹ and X ² is a fluorine atom. 5. In the above general formula (I), ring C is a 1,4-phenylene group substituted by one or more fluorine atoms.
The tetrahydronaphthalene derivative according to the above. 6. 2. The tetrahydronaphthalene derivative according to the above 1, wherein in formula (I), ring C is a trans-1,4-cyclohexylene group substituted by one or more fluorine atoms. 7. Wherein in general formula (I), Q is -CH ₂ CH ₂ -, - CF
The tetrahydronaphthalene derivative according to the above 1, wherein ＝ CF—, —CF ₂ O—, —OCF ₂ —, —C≡C— or a single bond. 8. In the general formula (I), Z is a fluorine atom or a carbon atom having 1 to 7 carbon atoms substituted by one or more fluorine atoms.
2. The tetrahydronaphthalene derivative according to the above 1, which is an alkyl group, an alkoxyl group, an alkenyl group, or an alkenyloxy group. 9. 2. The tetrahydronaphthalene derivative according to the above 1, wherein in the general formula (I), R is a straight-chain alkyl group or straight-chain alkoxyl group having 1 to 7 carbon atoms.

10. 2. A liquid crystal composition comprising the compound represented by the general formula (I) as described in 1 above. 11. 11. The liquid crystal composition according to the above item 10, which is used for driving an active matrix.

[12] A liquid crystal device comprising the liquid crystal composition according to the above item 10 as a constituent element. 13. 12. An active matrix driven liquid crystal display device using the liquid crystal composition according to the above item 11. Was found as a means for solving the above-mentioned problem.

[0020]

DESCRIPTION OF THE PREFERRED EMBODIMENTS An example of the present invention will be described below.

In order to solve the above problems, the present invention provides a compound represented by the general formula (I)

[0022]

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A novel liquid crystalline compound which is a tetrahydronaphthalene derivative represented by the formula:

In the formula (I), R is an aralkyl having 1 to 7 carbon atoms.
Alkoxyl or 1 to 7 halogen atoms
An alkyl group having 1 to 20 carbon atoms which may be substituted,
Alkoxyl, alkenyl or alkenyloxy
A carbon atom which may be substituted by a fluorine atom
An alkyl or alkenyl group having 1 to 7 atoms is preferred.
A straight-chain alkyl group having 1 to 7 carbon atoms or a straight-chain alkyl group.
A alkenyl group is more preferred. m and n are each independently
Indicates 0 or 1, but keeps viscosity low and enables high-speed response
For good performance, m = n = 0 is preferable, and excellent liquid crystal properties
At least one must be 1 to get
preferable. Ring A, and Ring B and Ring C, if present
Are each independently trans-1,4-cyclohexylene
Group, or substituted by one or more halogen atoms
1,4-phenylene group, pyridine-2,5-
Diyl group, pyrimidine-2,5-diyl group, pyrazine-
2,5-diyl group, pyridazine-3,6-diyl group,
Lance-1,3-dioxane-2,5-diyl group, tiger
Nsdecahydronaphthalene-2,6-diyl group, tetra
Hydronaphthalene-2,6-diyl group, naphthalene-
Represents a 2,6-diyl group, but trans-1,4-cyclo
Substituted by a hexylene group or one or two fluorine atoms
1,4-phenylene group which may be
Ring A is most preferably a trans-1,4-cyclohexylene group.
Preferably, ring C may be substituted by a fluorine atom
1,4-phenylene groups are most preferred. L, M and
Q is each independently -CH_TwoCH_Two-, -CH_TwoCH_TwoCH
_TwoCH_Two-, -CH = CH-, -CH = CHCH_TwoCH
_Two-, -CH_TwoCH_TwoCH = CH-, -CH (CH_Three) CH
_Two-, -CH_TwoCH (CH_Three)-, -CF = CF-, -C
H_TwoO-, -OCH_Two-, -CF _TwoO-, -OCF_Two−, −
Represents COO-, -OCO-, -C≡C- or a single bond
Is -CH_TwoCH_Two-, -CF = CF-, -CF_TwoO-,
-OCF_Two-, -COO-, -OCO-, -C≡C-,
Or a single bond is preferable, and -CH_TwoCH_Two-Or single bond
Is particularly preferred. When n = 1, the number of M and Q is small.
At least, on the other hand, when m = 1, at least L and Q
One is preferably a single bond. X¹, X^Twoand
X^ThreeEach independently represents a hydrogen atom or a fluorine atom
Is the case where no lateral substituent is present in ring A, ring B and ring C.
In order to improve the compatibility of the compound in
One is preferably a fluorine atom. Also, p-type liquid
When used as a crystalline compound, X¹And X^TwoAt least
One is preferably a fluorine atom, and is an n-type liquid crystal.
X^ThreeOr X^TwoAnd X^ThreeIs a fluorine atom
It is preferred that Z is a hydrogen atom, a halogen atom
Child, cyano group, cyanato group, or one or more fluorine
1 to 20 carbon atoms which may be substituted by an atom
Alkyl, alkoxyl, alkenyl, and alk
Represents an aryloxy group, and when ring C is an aromatic ring,
Atom, chlorine atom, trifluoromethoxy group, difluoro
Toxic group, 2,2,2-trifluoroethoxy group, 1,
1,2,2-tetrafluoroethoxy group, pentafluoro
Roethoxy group, trifluoromethyl group, cyano group, carbon
A linear alkyl group having 1 to 7 atoms and a double bond being a fluorine atom
Linear alkenyl having 2 to 7 carbon atoms which may be substituted
Or a carbon in which a double bond may be substituted by a fluorine atom
A linear alkenyloxy group having 3 to 7 is preferable, and fluorine
Atom, trifluoromethoxy group, cyano group, number of carbon atoms
A linear alkyl group having 2 to 7 carbon atoms, a linear alkyl group having 2 to 7 carbon atoms
Kenyl groups are particularly preferred. Further, ring C is a saturated ring (cyclo
Alkane), linear alkyl having 1 to 7 carbon atoms
Or a carbon in which a double bond may be substituted by a fluorine atom
A straight-chain alkenyl group having 2 to 7 atoms is preferred.

As mentioned above, the compound of the general formula (I)
R, Ring A, Ring B, Ring C, L, M, Q, m, n, Z and the choice of X ¹ , X ² and X ³ can encompass a very wide variety of compounds, but have the following general formula ( Ia) to (Ir).

[0026]

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Of these, more specifically, compounds represented by the following formulas (Iaa-1) to (Ira-1) are preferred.

[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[0034]

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[0035]

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[0036]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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[0054]

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[0055]

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[0057]

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[0058]

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[0059]

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[0060]

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[0062]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

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In the above formula, ^Ra is a linear alkyl group having 1 to 7 carbon atoms or a linear alkenyl group having 2 to 7 carbon atoms, and R ^b is a linear alkyl group having 1 to 7 carbon atoms. Or a straight-chain 3-alkenyl group having 4 to 7 carbon atoms, respectively. Z ^a is a fluorine atom, a chlorine atom, a cyano group, a trifluoromethoxy group, a difluoromethoxy group or a trifluoromethyl group, Z ^b may be substituted by a fluorine atom, a straight-chain alkyl having 1 to 7 carbon atoms Group, straight-chain alkoxyl group, straight-chain alkenyl group or straight-chain alkenyloxy group, Z ^c is a fluorine atom, a chlorine atom, a trifluoromethoxy group, a difluoromethoxy group or a trifluoromethyl group, and Z ^d is a fluorine atom, a chlorine atom. Atom, cyano group, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group, linear alkyl group having 2 to 7 carbon atoms, linear alkoxyl group, linear alkenyl group which may be substituted by fluorine atom or straight-chain alkenyloxy group, Z ^e may be substituted by fluorine atoms, straight of 1 to 7 carbon atoms Represents a chain alkyl group or a linear alkenyl group having 2 to 7 carbon atoms, respectively.

As the linear alkyl group which may be substituted by a fluorine atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a trifluoromethyl group are preferable. As the chain alkoxyl group, a methoxy group, an ethoxy group, a 2-methoxyethoxy group, a trifluoromethoxy group, a difluoromethoxy group are preferable, and as a linear alkenyl group which may be substituted by a fluorine atom, a vinyl group, a trans-1- Propenyl group, 3-butenyl group, trans-3
-A pentenyl group, a 2-fluoroethenyl group and a 2,2-difluoroethenyl group are preferred, and a straight-chain alkenyloxy group optionally substituted by a fluorine atom is 2-
Propenyloxy group, trans-2-butenyloxy group, trans-4-pentenyloxy group, trans-4
-Hexenyloxy groups are preferred.

In the above formula,

[0072]

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Represents a trans-1,4-cyclohexylene residue.

In order to obtain the compound of the general formula (I), which is a feature of the present invention, the compound represented by R, ring A, ring B, ring C, L,
According to M, Q, m, n, X ¹ , X ² , X ³ and Z, for example, it can be produced as follows.

Hereinafter, the method for producing the compound of the general formula (I) will be exemplified and described in detail according to the above (Ia) to (Ir).

(1) Production method of (Ia) (A) (Ia-1)

[0077]

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(Wherein R, rings C and Z have the same meanings as in formula (I))

(A-1) Cyclohexanone derivative (I
Ia)

[0080]

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(Wherein R has the same meaning as in general formula (I)) and pyrrolidine are dehydrated and condensed to give an enamine compound, which is then reacted with methyl vinyl ketone and, if necessary, acid-treated. (IIIa)

[0082]

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(Wherein R has the same meaning as in formula (I)).

(A-2) The above (IIIa) is oxidized with an oxidizing agent such as a mixture of cupric bromide and lithium bromide,
The following (IVa)

[0085]

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(Wherein, R represents the same meaning as in the general formula (I)). This compound is obtained by a Friedel-Crafts reaction between 2-naphthol or 2-methoxynaphthalene and an acyl chloride or an alkyl chloride in the presence of a Lewis acid such as aluminum chloride. It can also be obtained by selectively reducing naphthol, 6-acyl-2-methoxynaphthalene or 6-alkyl-2-methoxynaphthalene. Then, the above (IVa)
Is reacted with trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride in a solvent such as methylene chloride or chloroform in the presence of a base such as pyridine, diethylamine or triethylamine to obtain the following (Va)

[0087]

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(Wherein R has the same meaning as in the general formula (I), and Tf represents a trifluoromethanesulfonyl group).

(A-3) (Va) is converted to the following (VIa)

[0090]

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(Wherein rings C and Z have the same meanings as in general formula (I), X represents a halogen atom and more preferably a bromine atom) and a Grignard reagent prepared from magnesium and tetrakistridium In the presence of a transition metal catalyst (hereinafter abbreviated as catalyst 1) such as phenylphosphine palladium (0) or tetrakistriphenylphosphine nickel (0), tetrahydrofuran (TH
By reacting in a solvent such as F), (Ia-1) which is one form of the above (Ia) is obtained.

In particular, ring C may be optionally substituted 1,4
This method can be preferably used for an aromatic ring group such as -phenylene group or 2,6-naphthalenediyl group.

(A-4) Also, (Ia-1) is (V
Instead of Ia), the following (VIIa) produced from a Grignard reactant prepared from (VIa) and magnesium, and a trialkyl boric acid such as trimethyl boric acid

[0094]

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(Wherein, rings C and Z have the same meanings as in formula (I)).

This method can be preferably used particularly when the ring C is an aromatic ring group such as a 1,4-phenylene group or a 2,6-naphthalenediyl group which may have a substituent.

(I-5) Further, (Ia-1) is obtained by reacting the above (IIIa) with the above (VIa) and a Grignard reactant prepared from magnesium, followed by dehydration and the following (VIIIa)

[0098]

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Wherein R, rings C and Z are of the general formula (I)
Has the same meaning as in ) And then 2,3-
It can also be obtained by oxidizing with an oxidizing agent such as dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or bromine.

In particular, this method can be preferably used when the ring C is an aromatic ring group such as a 1,4-phenylene group and a 2,6-naphthalenediyl group which may have a substituent.

(B) (Ia-2) and (Ia-3)

[0102]

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Wherein R, rings C and Z are of the general formula (I)
Has the same meaning as in (IVa) is converted to bis (tetrafluoroborate) N, N'-
By fluorinating with a fluorinating agent such as difluoro-2,2'-dipyridinium or N-fluoro-5-trifluoromethoxypyridinium-2-sulfonate,
(IVb) and (IVc) below

[0104]

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(Wherein R has the same meaning as in formula (I)) is obtained, and then separated and purified by column chromatography, recrystallization and the like to obtain the respective compounds. Next, each compound was converted into the following (Vb) and (Vc) in the same manner as in (a-2).

[0106]

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(Wherein R has the same meaning as in general formula (I)), and then (a-3) or (a-
In the same manner as in 4), (Ia) is an embodiment of (Ia).
-2) and (Ia-3).

(C) The following (Ia)

[0109]

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Wherein R, ring C, X ¹ , X ² , X ³ and Z have the same meanings as in formula (I).

(C-1) The following (IXa)

[0112]

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(Wherein X ^a , X ^b , and X ^c each independently represent a hydrogen atom or a fluorine atom), is reacted with a chlorinating agent such as thionyl chloride to form an acid chloride, and aluminum chloride is present. Under the following reaction with ethylene gas, the following (Xa)

[0114]

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(Wherein X ¹ , X ² and X ³ have the same meanings as in formula (I)), and the carbonyl moiety is appropriately protected to give the following (Xb)

[0116]

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Wherein X ¹ , X ² and X ³ have the same meanings as in formula (I), and Y represents an optionally protected carbonyl group.

(C-2) The above (Xb) is lithiated with an alkyl lithium such as butyl lithium, reacted with a trialkyl boric acid such as trimethyl boric acid, and then oxidized and decomposed with a hydrogen peroxide solution to obtain the following. (XIa)

[0119]

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Wherein X ¹ , X ² and X ³ have the same meanings as in formula (I), and Y represents an optionally protected carbonyl group. Then, (A-
In the same manner as in 2), the following (XIIa)

[0121]

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(Wherein X ¹ , X ² and X ³ have the same meanings as in the general formula (I), Y represents an optionally protected carbonyl group, and Tf has the same meaning as described above. ), And then (XIIIa) in the same manner as in (a-3) or (a-4).

[0123]

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Wherein ring C, X ¹ , X ² , X ³ and Z have the same meanings as in formula (I), and Y represents an optionally protected carbonyl group.

Alternatively, instead of the above (XIIa), the above (Xb) is lithiated with an alkyl lithium such as butyl lithium and reacted with a halogen such as iodine to obtain the following (XIIb)

[0126]

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(Wherein X ¹ , X ² and X ³ have the same meanings as in general formula (I), Y represents an optionally protected carbonyl group, X ′ represents a halogen atom and an iodine atom (XIIIa) can also be obtained by using

(C-3) Y which is an optionally protected carbonyl group of the above (XIIIa) is appropriately deprotected to give a carbonyl compound, and then the following (XIVa)

[0129]

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(In the formula, R represents the same meaning as in the general formula (I), metal represents a metal residue of an organometallic compound, and is preferably magnesium or lithium monobromide.)
Grignard reagents such as ethyl magnesium bromide or 1-propyl magnesium bromide represented by
Alternatively, the above-mentioned (Ia) can be obtained by reacting with a nucleophilic organic metal such as an alkyllithium compound such as butyllithium, and then performing catalytic reduction under a hydrogen atmosphere with a reducing catalyst such as palladium carbon.

(C-4) Further, (Ia) is represented by (XII
In place of (Ia), (XVa)

[0132]

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(Wherein, R, X ¹ , X ² and X ³ have the same meanings as in the general formula (I)), and then, as in (c-2) above, the following (XVIa)

[0134]

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(Wherein, R, X ¹ , X ² and X ³ have the same meaning as in the general formula (I), and Tf has the same meaning as described above) or (XVIb)

[0136]

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(Wherein, R, X ¹ , X ² and X ³ have the same meanings as in the general formula (I), and X ′ has the same meanings as described above). it can.

(2) Production method of (Ib) (A) (Ib-1), (Ib-2) and (Ib-
3)

[0139]

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(Wherein R, ring A, ring C and Z have the same meaning as in general formula (I)) In place of the production method (IIa), the following (IIb)

[0141]

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(Wherein R and ring A have the same meanings as in formula (I)), except that (Ia-
(Ib-1), (Ib-2) and (Ib-3) in the same manner as in the production of 1), (Ia-2) and (Ia-3).
Can be obtained respectively.

(B) (Ib)

[0144]

Embedded image

(Wherein, R, ring A, ring C, X ¹ , X ² , X ³
And Z have the same meaning as in formula (I). )
In place of the above (XIVa), the following (XIVb)

[0146]

Embedded image

(Wherein R and ring A have the same meanings as in general formula (I), and metal has the same meanings as described above). (Ia)
b) can be obtained.

(3) Production method of (Ic) Instead of the above (VIa), the following (VIb)

[0149]

Embedded image

(Wherein, ring B, ring C and Z have the same meaning as in general formula (I), and X has the same meaning as described above), except that (Ia) is used. hand,
The above (Ic) can be obtained.

(4) Production method of (Id).

Instead of (IIa) and (VIa),
Other than using (IIb) and (VIb) respectively,
(Id) can be obtained in the same manner as in the production of (Ia).

(5) Production method of (Ie) (A) (Ie-1)

[0154]

Embedded image

(Wherein R, ring C, X ¹ , X ² , X ³ and Z have the same meanings as in formula (I))

[0156]

Embedded image

(Wherein rings C and Z have the same meanings as in formula (I)) in the presence of catalyst 1 in the presence of (Va)
(Vb), (Vc), (XIIa), (XIIb),
The compound is reacted with (XVIa) or (XVIb), and then, if necessary, in the same manner as in the production of (Ia), (Ie-1) which is a form of (Ie) can be obtained.

(B) (Ie-2)

[0159]

Embedded image

(Wherein R, ring C, X ¹ , X ² , X ³ and Z have the same meanings as in formula (I)).

(B-1) Lithiation of (Xb) or (XVa) with an alkyl lithium such as butyl lithium and the like, followed by reaction with a formylating agent such as DMF,
The following (XVIIIa)

[0162]

Embedded image

(Wherein, R, X ¹ , X ² and X ³ have the same meanings as in formula (I)) or

[0164]

Embedded image

(Wherein X ¹ , X ² and X ³ have the same meaning as in the general formula (I), and Y has the same meaning as described above).

(B-2) Then, each of (XVIIIa) and (XVIIIb) is combined with the following (XIXa)

[0167]

Embedded image

(Wherein, rings C and Z have the same meanings as in formula (I), and G is an oxydialkoxy phosphorus such as oxydiethoxylin, or a halogenated triphenyl such as triphenyl phosphorus bromide. And t-
By reacting with a Wittig reagent prepared from a strong base such as potassium butoxy and then optionally isomerizing a double bond, (Ie-2) and the following (XXa)

[0169]

Embedded image

Wherein ring C, X ¹ , X ² , X ³ and Z have the same meaning as in general formula (I), and Y has the same meaning as described above. (XXa) can be derived to (Ie-2) in the same manner as in the production of (Ia).

(C) (Ie-3)

[0172]

Embedded image

(Wherein R, ring C, X ¹ , X ² , X ³ and Z have the same meanings as in formula (I)).

(C-1) (Ie-3) can be obtained by catalytically reducing (Ie-2) with a reducing catalyst such as palladium carbon in a hydrogen atmosphere.

(C-2) The above (XXa) is catalytically reduced under a hydrogen atmosphere with a reducing catalyst such as palladium carbon or the like, and the following (XXIa)

[0176]

Embedded image

(Wherein, ring C, X ¹ , X ² , X ³ and Z have the same meaning as in general formula (I), and Y has the same meaning as described above), and then (Ia) (Ie-3) can be derived in the same manner as in the production of

(6) Production method of (If) (a) Triflate compound (XXIIa) which is an intermediate obtained in the production of (Ib)

[0179]

Embedded image

Wherein R, ring A, X ¹ , X ² and X ³
Has the same meaning as in formula (I). ), (If) is obtained in the same manner as in the production method of (Ie).

(B) The following intermediate (XVb) which is an intermediate obtained in the production of (Ib)

[0182]

Embedded image

Wherein R, ring A, X ¹ , X ² , and X ³
Has the same meaning as in formula (I). ), (If) is obtained in the same manner as in the production method of (Ie).

(C) In the same manner as in the production of (Ib) from (Xb), the following (XXIIIa)

[0185]

Embedded image

Wherein the rings C, Q, X ¹ , X ² , X ³ and Z have the same meanings as in the general formula (I), and Y has the same meanings as described above. Using (XIVb), (If) is obtained in the same manner as in the production of (Ia).

(7) Production method of (Ig) Instead of the above (VIa), the following (VIc)

[0188]

Embedded image

(Wherein ring B, ring C, Q and Z have the same meaning as in general formula (I), and X has the same meaning as described above), and are the same as in the preparation of the above (Ia). To produce (Ig).

(8) Production method of (Ih) Instead of the above (VIa), using the above (VIc),
(Ih) can be produced in the same manner as in the production of b).

(9) Production method of (Ii) (A) (Ii-1), (Ii-2) and (Ii-
3)

[0192]

Embedded image

(Wherein R, ring A, ring C, L and Z have the same meanings as in formula (I)) Production method (IIc)

[0194]

Embedded image

Wherein R, rings A and L are of the general formula (I)
Has the same meaning as in ) Using the above (Ia-
As in the production of 1), (Ia-2) and (Ia-3), one form of (Ii) (Ii-1), (Ii-
2) and (Ii-3) can be produced respectively.

(B) (Ii-4)

[0197]

Embedded image

(Wherein R, ring A, ring C, X ¹ , X ² , X ³
And Z have the same meaning as in formula (I). )
Manufacturing method

(Xa), (Xb), (XIIa),
After optionally deprotecting the optionally protected carbonyl group of (XIIb) or (XIIIa), it is reacted with a Wittig reagent such as methoxymethyltriphenylphosphonium chloride and acid-treated to give the following (XXIVa)

[0200]

Embedded image

(Wherein Tet. Represents a 1,2,3,4-tetrahydronaphthalen-2-yl group which may have a substituent). Then (XIXb)

[0202]

Embedded image

(Wherein R and ring A have the same meanings as in general formula (I), and G has the same meaning as described above) and t
-Reacting with a Wittig reagent prepared from a strong base such as potassium butoxy, and then optionally (Ia)
Is an embodiment of (Ii) in the same manner as in the production of (Ii-
4) can be obtained.

(C) (Ii-5)

[0205]

Embedded image

(Wherein, R, ring A, ring C, X ¹ , X ² , X ³
And Z have the same meaning as in formula (I). )
After the reaction between (XXIVa) and (XIXb), catalytic reduction is carried out in a hydrogen atmosphere with a reducing catalyst such as palladium carbon or the like, and then, if necessary, as in the production of (Ia), One form of (Ii-5) can be obtained.

In addition, (Ij), (Ik), (I
l), (Im), (In), (Io), (Ip), (I
In the production of q) and (Ir), it is possible to produce by appropriately combining and using the production methods described above in detail.

In addition, in obtaining the compound of the general formula (I), examples of a production method which can be preferably used particularly as an introduction method when Z is a cyano group are described.

That is, when the ring C is substituted by a halogen atom such as a chlorine atom, a bromine atom or an iodine atom, copper (I) cyanide is used in the presence of a base such as pyridine, quinoline, DMF or N-methylpyrrolidone. A method of converting to a cyano group by the action of a metal cyanide such as potassium cyanide, sodium cyanide or the like.

[0210]

Embedded image

Alternatively, ring C substituted with a hydroxy group
In the presence of a base, via trifluoromethanesulfonic acid chloride or trifluoromethanesulfonic anhydride or the like, via a conversion to an easily removable sensitive group such as triflate, and then, in the presence of catalyst 1, copper cyanide (I ), A method of converting into a cyano group by the action of a metal cyanide such as potassium cyanide or sodium cyanide as described below.

[0212]

Embedded image

Alternatively, after ring C is converted to an organometallic compound by lithiation or magnesium halide conversion,
After reacting with carbon dioxide or the like to introduce a carboxyl group, and then into an acid chloride compound with thionyl chloride or the like,
The following method for converting to a cyano group through amidation with ammonia or the like and dehydration with phosphorus oxychloride or the like.

[0214]

Embedded image

In addition, in obtaining the compound of the general formula (I), conventionally known methods can be used.

Representative examples of the compound represented by the general formula (I) thus produced are shown in Table 1.

[0219]

[Table 1]

(In the table, C indicates a crystal phase, N indicates a nematic phase, and I indicates an isotropic liquid phase.)

The compound represented by the general formula (I) is easy to obtain a high specific resistance and a high voltage holding ratio, has excellent compatibility with other liquid crystal compositions, and has good compatibility with other liquid crystal compounds. The mixture can be suitably used as a liquid crystal display cell material. The compound (I) can be used in any of the above-mentioned various display methods, but is suitable for use in a simple matrix drive or active matrix drive TN display element and an STN display element.

The composition provided by the present invention contains at least one compound represented by the general formula (I) as a first component, and particularly includes the following second to fourth components as other components. It is preferable to contain at least one kind.

That is, the second component is a so-called fluorine-based (halogen-based) p-type liquid crystal compound and has the following general formula (A)
1) to (A3).

[0222]

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In the above formula, R ^b represents an alkyl group having 1 to 12 carbon atoms, which may be linear or have a methyl or ethyl branch and may be a 3- to 6-membered cyclic group. may have a structure, any -CH present in the group ₂ -
Is -O-, -CH = CH-, -CH = CF-, -CF =
CH—, —CF ＝ CF— or —C≡C— may be replaced, and any hydrogen atom present in the group may be replaced by a fluorine atom or a trifluoromethoxy group, A linear alkyl group of Formulas 2 to 7,
A linear 1-alkenyl group having 2 to 7 carbon atoms, a linear 3-alkenyl group having 4 to 7 carbon atoms, and 1 carbon atom having a terminal substituted by an alkoxyl group having 1 to 3 carbon atoms
~ 5 alkyl groups are preferred. When an asymmetric carbon is generated by branching, the compound may be optically active or racemic.

Ring A, ring B and ring C are each independently substituted with a trans-1,4-cyclohexylene group, a transdecahydronaphthalene-trans-2,6-diyl group and at least one fluorine atom. 1,4-
Phenylene group, naphthalene-2,6-diyl group optionally substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group optionally substituted with one or more fluorine atoms, fluorine atom A 1,4-cyclohexenylene group optionally substituted with 1,3
-Dioxane-trans-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, but trans-1,4-cyclohexylene,
Transdecahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group optionally substituted by a fluorine atom or 1,4-optionally substituted by one or two fluorine atoms Phenylene groups are preferred. In particular, when ring B is a trans-1,4-cyclohexylene group or transdecahydronaphthalene-trans-
When it is a 2,6-diyl group, ring A is trans-1,
It is preferably a 4-cyclohexylene group, and when ring C is a trans-1,4-cyclohexylene group or transdecahydronaphthalene-trans-2,6-diyl group, ring B and ring A are trans-1 , 4-cyclohexylene. In (A3), ring A is preferably a trans-1,4-cyclohexylene group.

L ^a , L ^b and L ^c are linking groups, each independently being a single bond, an ethylene group (—CH ₂ CH
₂ -), 1,2-propylene group (-CH (CH ₃₎ CH ₂
- and _{-CH 2 CH (CH 3) -} ), 1,4- butylene group, -COO -, - OCO -, - OCF 2 -, - CF 2 O
-, -CH = CH-, -CH = CF-, -CF = CH
-, -CF = CF-, -C≡C- or -CH = NN =
CH— represents a single bond, an ethylene group, a 1,4-butylene group, —COO—, —OCF ₂ —, —CF ₂ O—, or —CF.
＝ CF— or —C≡C— is preferred, and a single bond or an ethylene group is particularly preferred. In (A2), at least one of them preferably represents a single bond in (A3).

Ring Z is an aromatic ring and has the following general formula (IX)
a) to (IXc).

[0227]

Embedded image

In the formula, Y ^{a to} Y ^j each independently represent a hydrogen atom or a fluorine atom, and in (IXa),
At least one of Y ^a and Y ^b is preferably a fluorine atom, in (IXb), it is preferable that at least one Y ^d to Y ^f is a fluorine atom, in particular Y ^d is a fluorine atom Is more preferred.

[0229] end group P ^a represents a fluorine atom, a chlorine atom, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group or difluoromethyl group or a carbon atoms substituted by two or more fluorine atoms 2 or 3
Represents an alkoxyl group, an alkyl group, an alkenyl group or an alkenyloxy group, preferably a fluorine atom, a trifluoromethoxy group or a difluoromethoxy group, and particularly preferably a fluorine atom.

In (A2), the compound of the general formula (I) of the present invention is excluded.

The third component is a so-called cyano-based p-type liquid crystal compound, which is a compound represented by the following formulas (B1) to (B3).

[0232]

Embedded image

In the above formula, R ^c represents an alkyl group having 1 to 12 carbon atoms, which may be linear or have a methyl or ethyl branch, and may be a 3- to 6-membered cyclic group. may have a structure, any -CH present in the group ₂ -
Is -O-, -CH = CH-, -CH = CF-, -CF =
CH—, —CF ＝ CF— or —C≡C— may be replaced, and any hydrogen atom present in the group may be replaced by a fluorine atom or a trifluoromethoxy group, A linear alkyl group of Formulas 2 to 7,
A linear 1-alkenyl group having 2 to 7 carbon atoms, a linear 3-alkenyl group having 4 to 7 carbon atoms, and 1 carbon atom having a terminal substituted by an alkoxyl group having 1 to 3 carbon atoms
~ 5 alkyl groups are preferred. When an asymmetric carbon is generated by branching, the compound may be optically active or racemic.

Ring D, ring E and ring F are each independently substituted with a trans-1,4-cyclohexylene group, a transdecahydronaphthalene-trans-2,6-diyl group and at least one fluorine atom. 1,4-
Phenylene group, naphthalene-2,6-diyl group optionally substituted with one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group optionally substituted with one or more fluorine atoms, fluorine atom A 1,4-cyclohexenylene group optionally substituted with 1,3
-Dioxane-trans-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, but trans-1,4-cyclohexylene,
Transdecahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group optionally substituted by a fluorine atom or 1,4-optionally substituted by one or two fluorine atoms Phenylene groups are preferred. In particular, when ring E is a trans-1,4-cyclohexylene group or transdecahydronaphthalene-trans-
When it is a 2,6-diyl group, ring D is trans-1,
It is preferably a 4-cyclohexylene group, and when ring F is a trans-1,4-cyclohexylene group or transdecahydronaphthalene-trans-2,6-diyl group, ring D and ring E are trans-1 , 4-cyclohexylene. In (B3), ring D is preferably a trans-1,4-cyclohexylene group.

[0235] L ^d, L ^e and L ^f is a linking group, are independently a single bond, an ethylene group (-CH ₂ CH
₂ -), 1,2-propylene group (-CH (CH ₃₎ CH ₂
- and _{-CH 2 CH (CH 3) -} ), 1,4- butylene group, -COO -, - OCO -, - OCF 2 -, - CF 2 O
-, -CH = CH-, -CH = CF-, -CF = CH
-, - CF = CF -, - C≡C -, - OCH 2 -, - C
H ₂ O-, or represent a -CH = NN = CH-, a single bond, an ethylene _{group, -COO -, - OCF 2 -} , - CF 2 O
—, —CF ＝ CF— or —C≡C— is preferred, and a single bond, an ethylene group or —COO— is particularly preferred. In (B2), at least one of them is (B2)
In 3), at least two of them preferably represent a single bond.

Ring Y is an aromatic ring represented by the following general formula (IX)
d) to (IXf).

[0237]

Embedded image

In the formula, Y ^{h to} Y ⁿ each independently represent a hydrogen atom or a fluorine atom, and in (IXe),
Y ⁿ and Y ^o are preferably hydrogen atoms. The terminal group Pa represents ^a cyano group (—CN), a cyanato group (—OCN) or —C≡CCN, and a cyano group is preferable.

In (B2), the compound of the general formula (I) of the present invention is excluded.

The fourth component has a dielectric anisotropy of about 0.
It is a so-called n-type liquid crystal, and has the following general formulas (C1) to (C
It consists of the compound shown in 3).

[0241]

Embedded image

In the above formula, R ^d and R ^e each independently represent an alkyl group having 1 to 12 carbon atoms, which may be linear or have a methyl or ethyl branch; may have a cyclic structure having 3 to 6-membered ring, any -CH ₂ present in the group - is -O -, - CH = CH-,
May be replaced by —CH ＝ CF—, —CF ＝ CH—, —CF ＝ CF— or —C≡C—, and any hydrogen atom present in the group is replaced by a fluorine atom or a trifluoromethoxy group , But may have 1 carbon atom
To 7 linear alkyl groups, 2 to 7 carbon atoms, linear 1
An alkenyl group, a linear 3-alkenyl group having 4 to 7 carbon atoms, a linear alkoxyl group having 1 to 3 carbon atoms, or 1 carbon atom having a terminal substituted by an alkoxyl group having 1 to 3 carbon atoms. 5 to 5 linear alkyl groups are preferred,
Further, at least one is a linear alkyl group having 1 to 7 carbon atoms, a linear 1-alkenyl group having 2 to 7 carbon atoms or a linear 3-alkenyl group having 4 to 7 carbon atoms. Particularly preferred.

Ring G, ring H, ring I and ring J each independently represent a trans-1,4-cyclohexylene group, a transdecahydronaphthalene-trans-2,6-diyl group, 1-2 fluorine atoms. 1,4-phenylene group which may be substituted by an atom or a methyl group, naphthalene-2 which may be substituted by one or more fluorine atoms,
6-diyl group, tetrahydronaphthalene-2,6-diyl group optionally substituted by 1 to 2 fluorine atoms, 1,4-cyclohexenylene optionally substituted by 1 to 2 fluorine atoms Group, 1,3-dioxane-
Represents a trans-2,5-diyl group, a pyrimidine-2,5-diyl group or a pyridine-2,5-diyl group, and in each compound, a trans-decahydronaphthalene-trans-2,6-diyl group; A naphthalene-2,6-diyl group which may be substituted by the above fluorine atom,
Tetrahydronaphthalene-2,6-diyl group optionally substituted by 1 to 2 fluorine atoms, 1,4-cyclohexenylene group optionally substituted by fluorine atom, 1,3-dioxane-trans- 2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-
It is preferred that the number of 2,5-diyl groups is one or less, and the other rings are trans-1,4-cyclohexylene groups or 1,4, which may be substituted by one or two fluorine atoms or methyl groups. -Preferably a phenylene group.

L ^g , L ^h and L ⁱ are linking groups, each independently being a single bond or an ethylene group (—CH ₂ CH
₂ -), 1,2-propylene group (-CH (CH ₃₎ CH ₂
- and _{-CH 2 CH (CH 3) -} ), 1,4- butylene group, -COO -, - OCO -, - OCF 2 -, - CF 2 O
-, -CH = CH-, -CH = CF-, -CF = CH
-, -CF = CF-, -C≡C- or -CH = NN =
It represents a CH-, single bond, ethylene group, 1,4-butylene group, -COO -, - OCO -, - OCF 2 -, - CF 2
O-, -CF = CF-, -C≡C- or -CH = NN
ＣＨCH— is preferred, and in (C2), at least one of them preferably represents a single bond in (C3).

In the compound (C2), the compound of the formula (I) of the present invention is excluded.

The more preferable form of (C1) can be represented by the following general formulas (C1a) to (C1h).

[0247]

Embedded image

In the above formulas, R ^f and R ^g each independently represent a linear alkyl group having 1 to 7 carbon atoms, a linear 1-alkenyl group having 2 to 7 carbon atoms, -C7 straight-chain 3-alkenyl group, C1-C3 straight-chain alkoxyl group or C1-C5 straight-chain alkyl substituted at the terminal with an C1-C3 alkoxyl group At least one of which is a linear alkyl group having 1 to 7 carbon atoms, a linear 1-alkenyl group having 2 to 7 carbon atoms or a linear 3-alkenyl group having 4 to 7 carbon atoms Represents However, when ring G1 to ring G8 are aromatic rings,
The corresponding R ^f is a group represented by the corresponding R ^g when the ring H1 to the ring H8 are an aromatic ring except for a 1-alkenyl group and an alkoxyl group.
Excludes a 1-alkenyl group and an alkoxyl group.

Ring G1 and ring H1 each independently represent a trans-1,4-cyclohexylene group, a transdecahydronaphthalene-trans-2,6-diyl group,
1,4-phenylene group optionally substituted by two fluorine atoms or methyl groups, naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, 1-2 fluorine atoms A tetrahydronaphthalene-2,6-diyl group optionally substituted with 1,4-cyclohexenylene group optionally substituted with 1 to 2 fluorine atoms, 1,3-dioxane-trans-
Represents a 2,5-diyl group, a pyrimidine-2,5-diyl group or a pyridine-2,5-diyl group, and in each compound, transdecahydronaphthalene-trans-2,
6-diyl group, naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, tetrahydronaphthalene-2,6-diyl group optionally substituted by one or two fluorine atoms A 1,4-cyclohexenylene group optionally substituted by a fluorine atom, 1,3
-Dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group is preferably one or less, in which case the other ring is trans-1,2 4-cyclohexylene group or 1
A 1,4-phenylene group which may be substituted by 2 to 2 fluorine atoms or methyl groups. Ring G2 and ring H2 each independently represent a trans-1,4-cyclohexylene group, transdecahydronaphthalene-trans-
2,6-diyl group, 1,4-phenylene group optionally substituted by 1 to 2 fluorine atoms or methyl groups, naphthalene-2,6-optionally substituted by 1 or more fluorine atoms Diyl group, tetrahydronaphthalene which may be substituted by 1 to 2 fluorine atoms
A 2,6-diyl group, a transdecahydronaphthalene-trans-2,6-diyl group, a naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, Tetrahydronaphthalene which may be substituted by 1 to 2 fluorine atoms
The number of 2,6-diyl groups is preferably one or less, in which case the other ring may be substituted by a trans-1,4-cyclohexylene group or one or two fluorine atoms or methyl groups. 1,4-phenylene group.
Ring G3 and ring H3 are each independently a 1,4-phenylene group optionally substituted with 1 to 2 fluorine atoms or a methyl group, and a naphthalene-2 optionally substituted with 1 or more fluorine atoms. , 6-diyl group, 1
Represents a tetrahydronaphthalene-2,6-diyl group which may be substituted by two or more fluorine atoms, and a naphthalene-2,6-diyl group which may be substituted by one or more fluorine atoms in each compound It is preferable that the number of tetrahydronaphthalene-2,6-diyl groups which may be substituted by one or two fluorine atoms is one or less.

A more preferred embodiment of (C2) can be represented by the following general formulas (C2a) to (C2m).

[0251]

Embedded image

In the above formula, ring G1, ring G2, ring G3, ring H
1, ring H2 and ring H3 have the same meanings as described above, ring I1 has the same meaning as ring G1, ring I2 has the same meaning as ring G2, and ring I3 has the same meaning as ring G3. In each of the above compounds, a transdecahydronaphthalene-trans-2,6-diyl group, a naphthalene-2,6-diyl group which may be substituted by one or more fluorine atoms, 1-2 fluorine atoms A tetrahydronaphthalene-2,6-diyl group optionally substituted with a 1,4-cyclohexenylene group optionally substituted with a fluorine atom, a 1,3-dioxane-trans-2,5-diyl group, Pyrimidine-2,
It is preferable that the number of 5-diyl group or pyridine-2,5-diyl group is one or less, and in that case, the other ring is trans-1,4-cyclohexylene group or 1-2 fluorine atoms or methyl group. Is a 1,4-phenylene group which may be substituted by

Next, a more preferred embodiment of (C3) can be represented by the following general formulas (C3a) to (C3f).

[0254]

Embedded image

In the above formula, ring G1, ring G2, ring H1, ring H
2, Ring I1 and Ring I2 have the same meanings as described above, and Ring J1 has the same meaning as Ring G1 and Ring J2 has the same meaning as Ring G2. Further, in each of the above compounds, a transdecahydronaphthalene-trans-2,6-diyl group, a naphthalene which may be substituted with one or more fluorine atoms,
2,6-diyl group, tetrahydronaphthalene-2,6-diyl group optionally substituted by 1 to 2 fluorine atoms, 1,4-optionally substituted by fluorine atom
The number of cyclohexenylene groups, 1,3-dioxane-trans-2,5-diyl groups, pyrimidine-2,5-diyl groups or pyridine-2,5-diyl groups is preferably one or less. The other ring is trans-1,4-
A cyclohexylene group or a 1,4-phenylene group which may be substituted by one or two fluorine atoms or a methyl group.

As is clear from the examples described below, the compounds of the present invention have excellent liquid crystallinity and excellent compatibility with liquid crystal compounds and liquid crystal compositions generally used today. In addition, it can be seen that the compound has an effect superior to conventional compounds in preparing a liquid crystal composition having a wide temperature range showing a liquid crystal phase, a low threshold voltage, and a high-speed response. In particular, the effect of reducing the threshold voltage is great, and it is extremely excellent as a liquid crystal material that can be driven at low voltage.

Therefore, the compound of the general formula (I) is in a mixture with other nematic liquid crystal compounds, and is particularly suitable for TN-type or STN-type field-effect display cells in a wide temperature range and low voltage driving. It can be suitably used as a possible liquid crystal material. Among the compounds of the formula (I), those having no strong polar group in the molecule can easily obtain a large specific resistance and a high voltage holding ratio, and should be used as components of a liquid crystal material for driving an active matrix. Is also possible. The present invention also provides a liquid crystal composition containing at least one compound represented by the general formula (I) as a component thereof.

[0258]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 2-propyl-6- (3,3
4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene (compound of I-1 shown in Table 1 above)
Synthesis of

[0260]

Embedded image

(1-a) 6-propyl-4,4a,
5,6,7,8-hexahydro-3H-naphthalene-2
Synthesis of -one 212 g of 4-propylcyclohexanone and 200 mL of pyrrolidine were dissolved in 600 mL of toluene, and heated with stirring for 3 hours to remove azeotropic water. Excess pyrrolidine was removed by azeotropic distillation with toluene to obtain 1- (4-propylcyclohex-1-en-1-yl) -pyrrolidine. The mixture was cooled to room temperature, and toluene 80
0 mL was added, and under cooling with a water bath, 120 mL of methyl vinyl ketone was added dropwise at 25 ° C or lower over 1 hour. After the completion of the dropwise addition, the mixture was heated immediately and refluxed for 20 hours. After cooling to room temperature, a buffer solution of pH 5 prepared with 63 g of sodium acetate, 120 mL of acetic acid and 140 mL of water was added, and the mixture was further heated under reflux for 4 hours. After cooling to room temperature, the organic layer was separated and washed with water and saturated saline. After drying over anhydrous sodium sulfate and evaporating the solvent, 6-propyl-4,4a, 5,5
320 g of a crude product of 6,7,8-hexahydro-3H-naphthalen-2-one was obtained.

(1-b) 2-propyl-6- (3,4
-Difluorophenyl) -1,2,3,4,8,8a-
Synthesis of hexahydronaphthalene 27.1 g of magnesium was suspended in 70 mL of tetrahydrofuran (THF), and 800 mL of THF was heated under reflux.
Of 3,4-difluorobromobenzene dissolved in
5.7 g was added dropwise. After stirring for an additional hour, under water cooling,
6-propyl-4,4a, 5 obtained in the above (1-a)
150 g of 6,7,8-hexahydro-3H-naphthalen-2-one was dissolved in 600 mL of THF and added dropwise with stirring. After stirring for another 2 hours, the mixture was cooled on ice and 10% hydrochloric acid was added.
000 mL was added dropwise. The mixture was extracted with toluene, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate.
Then, the crude product obtained by distilling off the solvent was dissolved in toluene 1
Dissolved in 200 mL, para-toluenesulfonic acid 14.9
g was added, and the mixture was heated with stirring for 3 hours to remove azeotropic water. After cooling to room temperature, the toluene layer was washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate, and the solvent was distilled off to give 2-propyl-6- (3,4-difluorophenyl) -1,1. 250 g of a crude product of 2,3,4,8,8a-hexahydronaphthalene was obtained.

(1-c) 2-propyl-6- (3,4-
Synthesis of difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (3,4) obtained in the above (1-b)
-Difluorophenyl) -1,2,3,4,8,8a-
The entire amount of the crude product of hexahydronaphthalene was dissolved in 1200 mL of methylene chloride, and the mixture was stirred under ice cooling with bromine 4
4.2 mL was added dropwise, and the mixture was further stirred for 3 hours. Then
An aqueous solution of sodium hydrogen sulfite was added, and after vigorous stirring for 30 minutes, the methylene chloride layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated, and 2-propyl-6- (3,
A crude product of (4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene was obtained. Then, the crude product is subjected to silica gel column chromatography (hexane).
After the purification, the residue was dissolved in 800 mL of ethyl acetate, and stirred with 20 g of 5% palladium carbon in a hydrogen atmosphere of 490 kPa in an autoclave for 6 hours. After filtration and evaporation of the solvent, 20 g of the obtained crude product (230 g) was purified by silica gel column chromatography (hexane), and then recrystallized three times from ethanol to give 2-propyl-6- (3,3). 4-difluorophenyl) -1,2,2
6.5 g of white crystals of 3,4-tetrahydronaphthalene were obtained.

The following compounds were obtained in the same manner. 2-methyl-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2-ethyl-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2-propyl-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2-methyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-methyl-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,4,5 -Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6 (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-methyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-ethyl -6- (4-Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4 -Tetrahydronaphthalene 2-butyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4 -Tetrahydronaphthalene 2-methyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-propyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-butyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene

Example 2 2-propyl-6- (3,
Synthesis of 4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene (compound of I-2 shown in Table 1 above)

[0266]

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(2-a) 2-propyl-1,2,3,
Synthesis of 4-tetrahydro-6-naphthol 6-propyl-4,4a, 5 obtained in (1-a)
5 g of 6,7,8-hexahydro-3H-naphthalen-2-one was dissolved in 10 mL of acetonitrile, and a solution of 11.6 g of copper (II) bromide and 2.3 g of lithium bromide in 50 mL of acetonitrile was added dropwise at room temperature. did. 2 more
After stirring for an hour, the solvent was distilled off, the residue was dissolved again in ethyl acetate, and the insoluble matter was removed by filtration, followed by washing with water and saturated saline. After drying over anhydrous sodium sulfate, the solvent is distilled off,
A crude product of 2-propyl-1,2,3,4-tetrahydro-6-naphthol was obtained.

(2-b) Synthesis of 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate 2-propyl-1,2,3 obtained in (2-a) , 4-
The crude product of tetrahydro-6-naphthol was dissolved in 20 mL of dichloromethane, 4.7 mL of trifluoromethanesulfonic anhydride was added thereto, suspended, and cooled to 5 ° C. While stirring vigorously, 4.6 mL of pyridine was added dropwise, and the mixture was further stirred for 1 hour. 20 mL of water was added to stop the reaction, and the organic layer was separated. The aqueous layer was extracted with 20 mL of dichloromethane, and the organic layers were combined, washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate, water and then saturated brine, and dried over anhydrous sodium sulfate and dried. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane) to obtain 3.8 g of 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate.

(2-c) 2-propyl-6- (3,4
Synthesis of 5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-trifluoromethanesulfonate obtained
3.8 g of 1,2,3,4-tetrahydronaphthalen-6-yl and 3,4,5-trifluorophenylboric acid (this is prepared from 3,4,5-trifluorobromobenzene and magnesium After reacting a Grignard reactant with trimethyl boric acid, the mixture was hydrolyzed with dilute hydrochloric acid (3.0 g), tetrakis (triphenylphosphine) palladium (0) 0.13 g, and potassium phosphate 3.6 g. And dimethylformamide (DMF)
Stirred at 80 ° C. for 10 hours in 20 mL. Thereafter, the mixture was cooled to room temperature, added with 20 mL of water, extracted with toluene, and the organic layer was washed with water and saturated saline in this order, and dried over anhydrous sodium sulfate and dried. The crude product obtained by evaporating the solvent was purified by silica gel column chromatography (hexane), and recrystallized three times from ethanol to give 2-propyl-6- (3,4,5-trifluorophenyl). )-
0.5 g of 1,2,3,4-tetrahydronaphthalene was obtained.

The following compounds were obtained in the same manner. 2-vinyl-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (3,4-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- ( Trans-1-propen-1-yl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-pentene-1 -Yl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene

2-vinyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6 − (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2-vinyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (2,3-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- (3-fluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (Trans-1-propen-1-yl) -6- (3
-Fluoro-4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (3-fluoro-
4-trifluoromethoxyphenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- (3
-Fluoro-4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2-vinyl-6- (3,5-difluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propene- 1-yl) -6
(3,5-difluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (3,5-difluoro-4-trifluoro Methoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6
(3,5-difluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-propyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,4,5 -Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4 -Tetrahydronaphthalene 2-butyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-trifluoromethoxyphenyl) -1,2,3,4 -Tetrahydronaphthalene 2-ethyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-propyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-butyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (3-fluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (3-fluoro- 4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3-fluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl -6- (3-Fluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,5-difluoro-4-trifluoromethoxyphenyl) -1,2 , 3,4-Tetrahydronaphthalene 2-propyl-6- (3,5-difluoro-4-trifluoromethoxyphenyl) -1,2,2 , 4-Tetrahydronaphthalene 2-butyl-6- (3,5-difluoro-4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,5-difluoro-4 -Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

Example 3 2- (trans-4-propylcyclohexyl) -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene (shown in Table 1 above) Of compound I-3)

[0275]

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(3-a) 2- (4-propylcyclohexyl) -6- (3,4,5-trifluorophenyl)
Synthesis of -1,2,3,4,8,8a-Hexahydronaphthalene Except that 4-propylcyclohexanone was replaced with 4- (4-propylcyclohexyl) -cyclohexanone in (1-a) of Example 1, Similarly, 6- (4-propylcyclohexyl) -4,4a, 5,6,7,8-
Hexahydro-3H-naphthalen-2-one was obtained. Next, in the same manner as in (1-b) except that 3,4,5-trifluorobromobenzene was used instead of 3,4-difluorobromobenzene, 2- (4-propylcyclohexyl) -6- (3 , 4,5-trifluorophenyl) -1,2,3,4,8,8a-hexahydronaphthalene was obtained.

(3-b) 2- (4-propylcyclohexyl) -6- (3,4,5-trifluorophenyl)
Synthesis of -1,2,3,4-tetrahydronaphthalene In 80 ml of toluene, 2-
(4-propylcyclohexyl) -6- (3,4,5-
Trifluorophenyl) -1,2,3,4,8,8a-
20 g of hexahydronaphthalene and 14 g of DDQ were stirred at room temperature for 3 hours. Water and toluene were added and the mixture was filtered. The toluene layer was separated, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate. After distilling off the solvent, silica gel column chromatography (hexane) was performed.
1 g of crude product was obtained. Next, the whole amount was dissolved in 80 mL of ethyl acetate, and stirred with 4 g of 5% palladium carbon in a hydrogen atmosphere of 490 kPa in an autoclave for 6 hours. After filtration and evaporation of the solvent, the obtained crude product was purified by silica gel column chromatography (hexane), and then recrystallized three times from ethanol / toluene to give 2- (4-propylcyclohexyl) -6- ( 3,
6.2 g of (4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene were obtained.

The following compounds were obtained in the same manner. 2- (trans-4-ethylcyclohexyl) -6
(4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene

2- (trans-4-propylcyclohexyl) -6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-butenyl) cyclohexyl] -6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-butenyl) cyclohexyl] -6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- [trans-4- (3-butenyl) cyclohexyl] -6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2- (trans-4-vinylcyclohexyl) -6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-butenyl) cyclohexyl] -6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-)
Yl) cyclohexyl] -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-butenyl) cyclohexyl] -6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-methylphenyl) -6- (4-fluorophenyl) -1,2,3, 4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-fluorophenyl)- 1,2,3,4-tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl) -6- (4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-methylphenyl) -6- (3,4-difluorophenyl) -1,2,2 , 4-Tetrahydronaphthalene 2- (4-ethylphenyl) -6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3,4 -Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- ( 4-n-pentylphenyl) -6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-methylphenyl) -6- (3,4,5-trifluorophenyl ) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (3 4,5-
(Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl) -6- (3,4,5
-Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2- (4-methylphenyl) -6- (4-
(Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4 -Propylphenyl) -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (4-trifluoromethoxyphenyl) -1, 2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl) -6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-methylphenyl) -6 -(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (2,3-diph (Orophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n- (Butylphenyl) -6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl) -6- (2,3-difluorophenyl) -1,2 , 3,4-Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene

2- (4-ethyl-2-fluorophenyl) -6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene

2- (4-ethyl-2-fluorophenyl) -6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(3,4-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3,4-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3,4-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3,4-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene

2- (4-ethyl-2,6-difluorophenyl) -6- (4-trifluoromethoxyphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(2,3-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (2,3-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(2,3-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (2,3-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene

Example 4 2-propyl-6- (4-
Cyano-3,5-difluorophenyl) -1,2,3
4-tetrahydronaphthalene (I-
Synthesis of compound 4)

[0286]

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(4-a) 2-propyl-6- (3,5
Synthesis of -difluorophenyl) -1,2,3,4-tetrahydronaphthalene In the same manner as in (1-b) except that 3,4-difluorobromobenzene was replaced with 3,5-difluorobromobenzene in Example 1 And 6-propyl-4,4a,
5,6,7,8-hexahydro-3H-naphthalene-2
212.5 g of 2-propyl-6- (3,5-difluorophenyl) -1,2,3,4,8,8a-hexahydronaphthalene was obtained from 200 g of -one. Then, (3
Further, distillation under reduced pressure was performed in the same manner as in -b) to give 2-propyl-6- (3,5-difluorophenyl) -1,2,2.
112 g of 3,4-tetrahydronaphthalene were obtained.

(4-b) 2-propyl-6- (3,5
-Difluoro-4-carbamoylphenyl) -1,2,2
Synthesis of 3,4-tetrahydronaphthalene 27.1 g of 2-propyl-6- (3,5-difluorophenyl) -1,2,3,4-tetrahydronaphthalene obtained in (4-a) was dissolved in 120 mL of THF, -50 ° C
N-butyl lithium 1.51M hexane solution 68.9
mL was added dropwise. Next, after blowing in carbon dioxide gas, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate. After evaporating the solvent, the crude product was dissolved in 80 mL of 1,2-dichloroethane, and 8.2 mL of thionyl chloride was added.
After a catalytic amount of pyridine was added dropwise thereto, the mixture was stirred at 50 ° C. for 2 hours, and then excess thionyl chloride and 1,2-dichloroethane were distilled off. The residue was dissolved in methylene chloride (100 mL), and ammonia gas was blown into the mixture while stirring at room temperature. After the exotherm had subsided, water was added, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline in this order. , And dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a crude product of 2-propyl-6- (3,5-difluoro-4-carbamoylphenyl) -1,2,3,4-tetrahydronaphthalene.

(4-c) 2-propyl-6- (4-cyano-3,5-difluorophenyl) -1,2,3,4
-Synthesis of tetrahydronaphthalene 2-propyl-6- (3,5) obtained in the above (4-b)
-Difluoro-4-carbamoylphenyl) -1,2,2
The total amount of the 3,4-tetrahydronaphthalene crude product was 12
It was dissolved in 0 mL of DMF, 13 mL of phosphorus oxychloride was added, and the mixture was reacted at 25 ° C. for 2 hours. The reaction solution was poured into ice water, diluted hydrochloric acid was added, and the aqueous layer was extracted with toluene. The organic layers were combined, washed with water, a saturated aqueous solution of sodium bicarbonate and saturated saline, and then dried and dried over anhydrous sodium sulfate. Silica gel column chromatography (toluene), then alumina column chromatography (toluene), then acetone solution, purified by activated carbon treatment, and recrystallized seven times from ethanol to give 2-propyl-6- (4-cyano-3,5 -Difluorophenyl)
−1,2,3,4-tetrahydronaphthalene 4.0 g was obtained.

The following compounds were obtained in the same manner. 2-ethyl-6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (3-fluoro-4-cyanophenyl) -1,2,3 4-tetrahydronaphthalene 2-butyl-6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3-fluoro-4-cyanophenyl) -1, 2,3,4-tetrahydronaphthalene 2-ethyl-6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,5-difluoro- 4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaph Len 2- (trans-4-ethyl-cyclohexyl) -6-
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans -4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3,5-difluoro-
4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3,5-difluoro-
4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene

2- (4-ethylphenyl) -6- (3-
Fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3-fluoro-
4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl) -6- (3-fluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (3,5- Difluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (4-n-butylphenyl) -6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-n-pentylphenyl ) -6- (3,5-difluoro-4-cyanophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6- (3
-Fluoro-4-cyanophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6- (3
-Fluoro-4-cyanophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3-fluoro-4-cyanophenyl) -1,2,3
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene

2- (4-ethyl-2,6-difluorophenyl) -6- (3-fluoro-4-cyanophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3-fluoro-4-cyanophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3-Fluoro-4-cyanophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3-fluoro-4-cyanophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3,5-difluoro-4-cyanophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3,5-difluoro-4-cyanophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3,5-difluoro-4-cyanophenyl)-
1,2,3,4-tetrahydronaphthalene

Example 5 2-propyl-5-fluoro-6- (3,4,5-trifluorophenyl) -1,
Synthesis of 2,3,4-tetrahydronaphthalene and 2-propyl-7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene (see Table 1 above) Compound of I-5 shown)

[0294]

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(5-a) 2-propyl-5-fluoro-
Synthesis of 1,2,3,4-tetrahydro-6-naphthol and 2-propyl-7-fluoro-1,2,3,4-tetrahydro-6-naphthol 2-propyl- obtained in (2-a) 1,2,3,4-
200 g of tetrahydro-6-naphthol was dissolved in 1000 mL of dichloromethane, and 5 g of sodium trifluoromethanesulfonate was added, followed by vigorous stirring. to this,
Bistetrafluoroborate N, N'-difluoro-2,
243 g of 2'-dipyridinium was gradually added, and 5
Stirred at room temperature for hours. Water and then a 10% aqueous sodium hydroxide solution were added to decompose the excess fluorinating agent, and after returning to acidic with dilute hydrochloric acid, the organic layer was separated. The aqueous layer was extracted with dichloromethane, and the organic layers were combined, washed with water and then with a saturated saline solution, and dried and dried over anhydrous sodium sulfate. The crude product obtained by evaporating the solvent was separated and purified by silica gel column chromatography (toluene) to give 2-propyl-5.
-Fluoro-1,2,3,4-tetrahydro-6-naphthol 57.0 g and 2-propyl-7-fluoro-
1,2,3,4-tetrahydro-6-naphthol
5 g of each were obtained.

(5-b) 2-propyl-5-fluoro-
6- (3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene and 2-propyl-
Synthesis of 7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene In (2-b), 2-propyl-1,2,3,4-tetrahydro- In place of 6-naphthol, the aforementioned (5-a)
2-propyl-5-fluoro-1,2,3,4- obtained in
Tetrahydro-6-naphthol and 2-propyl-7
-Fluoro-1,2,3,4-tetrahydro-6-naphthol, except that (2-b) and (2
2-propyl-5-fluoro-6 in the same manner as in -c)
-(3,4,5-trifluorophenyl) -1,2,2
35 g of 3,4-tetrahydronaphthalene and 53 g of 2-propyl-7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene were obtained.

The following compounds were obtained in the same manner. 2-ethyl-5-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (4-fluorophenyl) -1,2,3, 4-tetrahydronaphthalene 2-butyl-5-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (4-fluorophenyl) -1, 2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (4-fluorophenyl) -1,2,3 4
-Tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans -4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5 Fluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (3,4-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (3,4-difluorophenyl) -1, 2,
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (3,4-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) -1,2 ,
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydro Naphthalene 2-pentyl-5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6 −
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (3,4,5-trifluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (3,4,5-trifluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (3,4,5-trifluorophenyl) -1,2 , 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (4-trifluoromethoxyphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (4-trifluoromethoxyphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,3 4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5 Fluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (2,3-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (2,3-difluorophenyl) -1, 2,
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (2,3-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) -1,2 ,
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene

2-ethyl-7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (4-fluorophenyl) -1,2 , 3,4-Tetrahydronaphthalene 2-butyl-7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (4-fluorophenyl) -1,2,3 4
-Tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans -4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6- (4
-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3
4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-7- Fluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (3,4-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (3,4-difluorophenyl) -1, 2,
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (3,4-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) -1,2 ,
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene

2-ethyl-7-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydro Naphthalene 2-pentyl-7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6 −
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (3,4,5-trifluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (3,4,5-trifluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (3,4,5-trifluorophenyl) -1,2 , 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6 (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (4-trifluoromethoxyphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (4-trifluoromethoxyphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3 4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-)
Yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6- (4
-Trifluoromethoxyphenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-7- Fluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (2,3-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (2,3-difluorophenyl) -1, 2,
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (2,3-difluorophenyl) -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) -1,2 ,
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene

Example 6 2-propyl-6- (3,3)
4,5-trifluorophenyl) ethynyl-1,2,2
Synthesis of 3,4-tetrahydronaphthalene

[0308]

Embedded image

50 g of 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate obtained in (2-b) and 2- (3,4,5-trifluorophenyl)- 33.9 g of acetylene, tetrakis (triphenylphosphine) palladium (0) 3.
6 g, and 51.4 g of potassium phosphate were added to DMF20.
The mixture was stirred at 0 ° C. for 10 hours in 0 mL. Thereafter, the mixture was cooled to room temperature, water was added, and the mixture was extracted with toluene. The organic layer was washed with water and saturated saline in this order, and dried and dried over anhydrous sodium sulfate. The crude product obtained by evaporating the solvent was purified by silica gel column chromatography (hexane), and further recrystallized three times from ethanol to give 2-propyl-6.
-(3,4,5-trifluorophenyl) ethynyl-
32.6 g of 1,2,3,4-tetrahydronaphthalene was obtained.

In the same manner, the following compound was obtained. 2-ethyl-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4 -Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-fluorophenyl) ethynyl-1,2,3, 4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-fluorophenyl) Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2- Fluorophenyl) -6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(4-Fluorophenyl) ethynyl-1,2,3,4
-Tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (4-fluorophenyl) ethynyl-1,2,3
4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(4-Fluorophenyl) ethynyl-1,2,3,4
-Tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (4-fluorophenyl) ethynyl-1,2,3
4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -6
-(4-Fluorophenyl) ethynyl-1,2,3,4
-Tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
6- (4-fluorophenyl) ethynyl-1,2,3
4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -6
-(4-Fluorophenyl) ethynyl-1,2,3,4
-Tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
6- (4-fluorophenyl) ethynyl-1,2,3
4-tetrahydronaphthalene

2-ethyl-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-6- (3,4-difluorophenyl) ethynyl-1,2,3 , 4-Tetrahydronaphthalene 2-butyl-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,4-difluorophenyl) ethynyl-1,2 , 3,4-Tetrahydronaphthalene 2- (3-buten-1-yl) -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-3-pentene- 1-yl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [ Trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (3,4-difluorophenyl) ethynyl-1, 2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6 (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- (4-ethyl-2-fluorophenyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3,4-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3,4-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -6
-(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
6- (3,4-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -6
-(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
6- (3,4-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene

2-ethyl-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-6- (3,4,5-trifluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl ) -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (3,4,5-trifluoro Phenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (3,4,5- (Trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -6
-(3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
6- (3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -6
-(3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
6- (3,4,5-trifluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene

2-ethyl-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3 , 4-Tetrahydronaphthalene 2-butyl-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-trifluoromethoxyphenyl) ethynyl-1,2 , 3,4-Tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-3-pentene- 1-yl) -6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -[Trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-trifluoromethoxyphenyl) ethynyl-1, 2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6 (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- (4-ethyl-2-fluorophenyl) -6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -6
-(4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -6
-(4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
6- (4-trifluoromethoxyphenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene

2-ethyl-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-6- (2,3-difluorophenyl) ethynyl-1,2,3 , 4-Tetrahydronaphthalene 2-butyl-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-6- (2,3-difluorophenyl) ethynyl-1,2 , 3,4-Tetrahydronaphthalene 2- (3-buten-1-yl) -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-3-pentene- 1-yl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [ Trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (2,3-difluorophenyl) ethynyl-1, 2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6 (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- (4-ethyl-2-fluorophenyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -6
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -6
-(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
6- (2,3-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -6
-(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
6- (2,3-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -6
-(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
6- (2,3-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -6
-(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
6- (2,3-difluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene

2-ethyl-5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (4-fluorophenyl) ethynyl-1 , 2,3,4-Tetrahydronaphthalene 2-butyl-5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (4- Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl- 5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( Trans-4-propylcyclohexyl) -5
Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-butyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-5-fluoro-6- ( 3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3 , 4-Tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2-
(Trans-4-ethylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5 −
Fluoro-6- (3,4,5-trifluorophenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4- Tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (3,4,5-trifluorophenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2 -Fluorophenyl) -5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3
4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-5-fluoro-6- (4-trifluoromethoxy Phenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-butene -1-yl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (Trans-4-ethylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -5
Fluoro-6- (4-trifluoromethoxyphenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(Trans-4-pentylcyclohexyl) -5-
Fluoro-6- (4-trifluoromethoxyphenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -[Trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4 -(Trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,
4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,
4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( 4-propyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5 -Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (4-trifluoromethoxy Phenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-5-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl- 5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -5-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( Trans-4-propylcyclohexyl) -5
Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -5
Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -5-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -5-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-butyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-ethyl-2,6-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene2-
(4-pentyl-2,6-difluorophenyl) -5
Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -5
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (4-fluorophenyl) ethynyl-1 , 2,3,4-Tetrahydronaphthalene 2-butyl-7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (4- Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6- (4
-Fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(4-fluorophenyl) ethynyl-1,2,3,4-
Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (4-fluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-fluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (4-fluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl- 7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( Trans-4-propylcyclohexyl) -7-
Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,4
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(3,4-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-butyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-7-fluoro-6- ( 3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3 , 4-Tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydro Naphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) ) -7-
Fluoro-6- (3,4,5-trifluorophenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4- Tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (3,4,5-trifluorophenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (3,
4,5-trifluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(3,4,5-trifluorophenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2 -Fluorophenyl) -7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro -6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (3,4,5-trifluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3
4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl-7-fluoro-6- (4-trifluoromethoxy Phenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (3-butene -1-yl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (Trans-4-ethylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) -7-
Fluoro-6- (4-trifluoromethoxyphenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(Trans-4-pentylcyclohexyl) -7-
Fluoro-6- (4-trifluoromethoxyphenyl)
Ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -[Trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4 -(Trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,
4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,
4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6- (4
-Trifluoromethoxyphenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(4-trifluoromethoxyphenyl) ethynyl-1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( 4-propyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -7 -Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (4-trifluoromethoxy Phenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (4-trifluoromethoxyphenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

2-Ethyl-7-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-propyl-7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-butyl- 7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2-pentyl-7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -7-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- ( Trans-4-propylcyclohexyl) -7-
Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -7-
Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,2 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -7-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -7-fluoro-6- (2,3
-Difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -7-fluoro-6-
(2,3-difluorophenyl) ethynyl-1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-butyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2 -(4-ethyl-2,6-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl) -7
-Fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
7-fluoro-6- (2,3-difluorophenyl) ethynyl-1,2,3,4-tetrahydronaphthalene

Example 7 2- (4-propylphenyl) -6- (3,4,5-trifluorophenyl)-
Synthesis of 5,7-difluoro-1,2,3,4-tetrahydronaphthalene

[0326]

Embedded image

(7-a) 5,7-difluoro-1,
Synthesis of 2,3,4-tetrahydronaphthalen-2-one A catalytic amount of pyridine was added to a solution of 200 g of 5,7-difluorophenylacetic acid and 300 g of thionyl chloride in 400 mL of 1,2-dichloroethane, and the mixture was heated and refluxed for 5 hours in a nitrogen atmosphere. Thereafter, 1,2-dichloroethane and excess thionyl chloride were distilled off. The obtained residue was cooled under −20 ° C., dichloromethane 1000 mL, aluminum chloride 3
Add dropwise to 20 g. After stirring for 30 minutes, ethylene gas was blown in, and the mixture was further stirred for 5 hours. Dilute hydrochloric acid was added, the organic layer was separated, and the aqueous layer was extracted with toluene. The organic layers were combined, washed sequentially with water, saturated aqueous sodium bicarbonate, water and saturated saline, dried over anhydrous sodium sulfate and dried, and the solvent was distilled off.
17 of 2,3,4-tetrahydronaphthalen-2-one
0 g was obtained.

(7-b) Synthesis of 2- (4-propylphenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalene 9.5 g of magnesium was suspended in 30 mL of THF, and the suspension was heated under reflux. 68.9 g of 4-propylbromobenzene dissolved in 270 mL of THF was added dropwise. After further stirring for 1 hour, the 5,6-difluoro-1,2,3,4-tetrahydroxy-2-one 6 obtained in the above (7-a) was cooled with water.
0 g was dissolved in 120 mL of THF and added dropwise with stirring.
After further stirring for 2 hours, the mixture was cooled on ice and 10% hydrochloric acid 100m
L was added dropwise. The organic layer was extracted with toluene, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate.
Then, the crude product obtained by distilling off the solvent was dissolved in toluene 2
The mixture was dissolved in 50 mL, 5 g of paratoluenesulfonic acid was added, and the mixture was heated with stirring for 3 hours to remove azeotropic water. After cooling to room temperature, the toluene layer was washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a crude product. Then, ethyl acetate 280
Then, 11 g of 5% palladium carbon was added in a hydrogen atmosphere of 490 kPa in an autoclave, and the mixture was stirred for 6 hours. After filtration and evaporation of the solvent, the resulting crude product was purified by silica gel column chromatography (hexane),
2- (4-propylphenyl) -5,7-difluoro-
64.4 g of 1,2,3,4-tetrahydronaphthalene was obtained.

(7-c) 2- (4-propylphenyl) -6-iodo-5,7-difluoro-1,2,3
Synthesis of 4-tetrahydronaphthalene 2- (4-propylphenyl)-obtained in the above (7-b)
64.4 g of 5,7-difluoro-1,2,3,4-tetrahydronaphthalene was dissolved in 260 mL of THF, and -5
While cooling to 0 ° C., 164 mL of a 1.51 M hexane solution of n-butyllithium was added dropwise. Then, THF200mL
68.5 g of iodine dissolved in was added dropwise, and after stirring for 2 hours,
The reaction was stopped by adding 200 mL of water. After returning to room temperature, the organic layer was washed with an aqueous sodium hydrogen sulfite solution and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 95 g of a crude product of 2- (4-propylphenyl) -6-iodo-5,7-difluoro-1,2,3,4-tetrahydronaphthalene.

(7-d) 2- (4-propylphenyl) -6- (3,4,5-trifluorophenyl)-
Synthesis of 5,7-difluoro-1,2,3,4-tetrahydronaphthalene 2-propyl-1,2,2,2-trifluoromethanesulfonate
2- (4-propylphenyl) -6 obtained in the above (7-c) in place of 3,4-tetrahydronaphthalen-6-yl
-Iodo-5,7-difluoro-1,2,3,4-tetrahydronaphthalene was used and reacted with 3,4,5-trifluorophenylboric acid in the same manner as in (2-c), to obtain 2 -(4-propylphenyl) -6- (3,4,
5-trifluorophenyl) -5,7-difluoro-
58.1 g of 1,2,3,4-tetrahydronaphthalene was obtained.

In the same manner, the following compound was obtained. 2-ethyl-5,7-difluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5,7-difluoro-6- (4-fluorophenyl) -1, 2,3,4-tetrahydronaphthalene 2-butyl-5,7-difluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7-difluoro-6- ( 4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7-difluoro-6
-(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7-difluoro-
6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7-difluoro-6
-(4-Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7-difluoro-
6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7-
Difluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5,7
-Difluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7-
Difluoro-6- (4-fluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5,7
-Difluoro-6- (4-fluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7-difluoro-6
(3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7-difluoro-6- (3,4-difluorophenyl ) -1,2,3,4-Tetrahydronaphthalene 2- (4-ethylphenyl) -5,7-difluoro-6
-(3,4-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propylphenyl) -5,7-difluoro-
6- (3,4-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-butylphenyl) -5,7-difluoro-6
-(3,4-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentylphenyl) -5,7-difluoro-
6- (3,4-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7-
Difluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5,7
-Difluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7-
Difluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5,7
-Difluoro-6- (3,4-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7-difluoro-6
(3,4,5-trifluorophenyl) -1,2,3,
4-tetrahydronaphthalene 2-propyl-5,7-difluoro-6- (3,4,5
-Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7-difluoro-6- (3,4,5-
(Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7-difluoro-6- (3,4,5
-Trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7-difluoro-6
-(3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7-difluoro-6
-(3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7-difluoro-
6- (3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7-
Difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5,7
-Difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7-
Difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5,7
-Difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7-difluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7-difluoro-6
(4-trifluoromethoxyphenyl) -1,2,3,
4-tetrahydronaphthalene 2-propyl-5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7-difluoro-6- (4- (Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- ( 4-ethylphenyl) -5,7-difluoro-6
-(4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7-difluoro-
6- (4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7-difluoro-6
-(4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7-difluoro-
6- (4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7-
Difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5,7
-Difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7-
Difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5,7
-Difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7-difluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

2-ethyl-5,7-difluoro-6
(2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7-difluoro-6- (2,3-difluorophenyl ) -1,2,3,4-Tetrahydronaphthalene 2- (4-ethylphenyl) -5,7-difluoro-6
-(2,3-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propylphenyl) -5,7-difluoro-
6- (2,3-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-butylphenyl) -5,7-difluoro-6
-(2,3-difluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentylphenyl) -5,7-difluoro-
6- (2,3-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7-
Difluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5,7
-Difluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7-
Difluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5,7
-Difluoro-6- (2,3-difluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7-difluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7,8-trifluoro-
6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-5,7,8-trifluoro-6- (4-
Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl- 5,7,8-trifluoro-6- (4-
Fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-propylphenyl) -5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-butylphenyl) -5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-
Tetrahydronaphthalene 2- (4-pentylphenyl) -5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5
7,8-trifluoro-6- (4-fluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (4-fluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5
7,8-trifluoro-6- (4-fluorophenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-fluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7,8-trifluoro-
6- (3,4-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2-propyl-5,7,8-trifluoro-6- (3
4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7,8-trifluoro-6- (3,4
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7,8-trifluoro-6- (3
4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5
7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5
7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4-difluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7,8-trifluoro-
6- (3,4,5-trifluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2-propyl-5,7,8-trifluoro-6- (3
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7,8-trifluoro-6- (3
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7,8-trifluoro-6- (3,
4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7,8-trifluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7,8-trifluoro-6- (3,4,5-trifluorophenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5
7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5
7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (3,4,5-trifluorophenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7,8-trifluoro-
6- (4-trifluoromethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-propyl-5,7,8-trifluoro-6- (4-
(Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7,8-trifluoro-6- (4-
(Trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5
7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5
7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (4-trifluoromethoxyphenyl) -1,2,3,4-tetrahydronaphthalene

2-Ethyl-5,7,8-trifluoro-
6- (2,3-difluorophenyl) -1,2,3,4
-Tetrahydronaphthalene 2-propyl-5,7,8-trifluoro-6- (2,
3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-butyl-5,7,8-trifluoro-6- (2,3
-Difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2-pentyl-5,7,8-trifluoro-6- (2,
3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (4-ethyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2-fluorophenyl) -5
7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2-fluorophenyl) -5,7,
8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2-fluorophenyl) -5
7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,6-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-pentyl-2,3-difluorophenyl)-
5,7,8-trifluoro-6- (2,3-difluorophenyl) -1,2,3,4-tetrahydronaphthalene

Example 8 2- [2- (trans-4)
-Propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

[0342]

Embedded image

(8-a) 5,7-difluoro-1,
Synthesis of 2,3,4-tetrahydronaphthalene-2-carbaldehyde 131.7 g of methoxymethyltriphenylphosphonium chloride and 46.2 potassium tert-butoxychloride in THF under ice cooling.
A solution of 50 g of 5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-one obtained in (7-a) in 250 mL of THF was added dropwise to the Wittig reagent prepared from the above at 0 ° C. After reacting for 1 hour, the temperature was returned to room temperature, water was added, and the organic layer was concentrated. Hexane was added for dissolution, and the insoluble triphenylphosphine oxide was separated by filtration and washed with a mixed solvent of methanol / water = 1/1. The crude product obtained by concentrating the hexane layer was diluted with 250 mL of T
It was dissolved in HF, 200 mL of diluted hydrochloric acid was added, and the mixture was refluxed for 3 hours. Toluene was added, washed with water, dried over anhydrous sodium sulfate and dried, and the solvent was distilled off to obtain 46.5 g of 5,7-difluoro-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde.

(8-b) 2- [2- (trans-4-
Synthesis of propylcyclohexyl) ethyl] -5,7-difluoro-1,2,3,4-tetrahydronaphthalene 2- (trans-4-propylcyclohexyl) ethyltriphenylphosphonium bromide 17 in THF under ice-cooling
The Wittig reagent prepared from 1.2 g and 39.9 g of potassium t-butoxy was added to the 5,7-
The whole amount of difluoro-1,2,3,4-tetrahydronaphthalene-2-carbaldehyde was dissolved in 250 mL of THF, and added dropwise at 0 ° C. After reacting for 1 hour, the temperature was returned to room temperature, water was added, and the organic layer was concentrated. Hexane was added for dissolution, and the insoluble triphenylphosphine oxide was separated by filtration and washed with a mixed solvent of methanol / water = 1/1. The crude product obtained by concentrating the hexane layer was dissolved in 200 mL of ethyl acetate, 4 g of 5% palladium carbon was added, and the mixture was stirred in an autoclave under a hydrogen pressure of 490 kPa. After stirring at room temperature for 5 hours, the catalyst was removed by filtration through Celite, the solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane) to give 2- [2- (trans-4-propylcyclohexyl) ethyl] -5,7-. Difluoro-1,2,3,4-tetrahydronaphthalene 53.9 g
I got

(8-c) 2- [2- (trans-4-
Propylcyclohexyl) ethyl] -5,7-difluoro-6- (4-oxocyclohexyl) -1,2,3,
Synthesis of 4-tetrahydronaphthalene 2- [2- (trans-4) in the same manner as in the above (7-c).
-Propylcyclohexyl) ethyl] -5,7-difluoro-1,2,3,4-tetrahydronaphthalene 53.
From 9 g, 2- [2- (trans-4-propylcyclohexyl) ethyl] -5,7-difluoro-6-iodo-
74.1 g of 1,2,3,4-tetrahydronaphthalene
I got Next, this was dissolved in 250 mL of THF, and added dropwise to a suspension of 4.5 g of magnesium and 15 mL of THF under heating and reflux to prepare a Grignard reagent. After cooling to room temperature, 28.52 g of cyclohexane-1,4-dione monoethylene acetal was dissolved in 60 mL of THF and added dropwise. After stirring for 3 hours, 10% hydrochloric acid was added, and the temperature was raised.
The aqueous layer was extracted with toluene, and the combined organic layers were washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate. The concentrate obtained by distilling off the solvent was dissolved in 250 mL of toluene, dehydrated with potassium hydrogen sulfate, and heated to reflux while adding ethylene glycol and removing azeotropic water from the system. The mixture was cooled to room temperature, washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, dried over anhydrous sodium sulfate and dried, and the solvent was distilled off.
L in ethyl acetate, 7 g of 5% palladium carbon
Was added and the mixture was stirred in an autoclave under a hydrogen pressure of 490 kPa. The catalyst was removed by filtration through Celite, the solvent was distilled off, and the mixture was heated and stirred in an aqueous formic acid solution. After cooling, water was added, the mixture was extracted with toluene, washed with water, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline in this order, and the solvent was distilled off. The concentrate was purified by silica gel column chromatography (hexane-toluene) to give 2- [2- (trans-4-propylcyclohexyl) ethyl] -5,7-difluoro-6-.
49.1 g of (4-oxocyclohexyl) -1,2,3,4-tetrahydronaphthalene were obtained.

(8-d) 2- [2- (trans-4-
Propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4-hydroxyphenyl)
Synthesis of cyclohexyl] -1,2,3,4-tetrahydronaphthalene 4-methoxybromobenzene 2 in 100 mL of THF
A Grignard reagent was prepared from 4.2 g and 3.2 g of magnesium. Here, 2- [2] obtained in the above (8-c)
-(Trans-4-propylcyclohexyl) ethyl]
The whole amount of -5,7-difluoro-6- (4-oxocyclohexyl) -1,2,3,4-tetrahydronaphthalene was dissolved in 100 mL of THF, and the solution was added dropwise at room temperature. Three
After stirring for 10 hours, 10% hydrochloric acid was added. After stirring for another 2 hours, the mixture was cooled to room temperature, the aqueous layer was extracted with toluene, and the combined organic layers were washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate. Dried. The solvent was distilled off, and the obtained concentrate was dissolved in 200 mL of toluene.
g, and the mixture was heated under reflux for 3 hours to remove water azeotropically heated. After cooling to room temperature, the toluene layer was washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate.
The solvent was distilled off, and the concentrate obtained was 250 mL of ethyl acetate.
And stirred in an autoclave with 5 g of 5% palladium carbon in a hydrogen atmosphere of 490 kPa for 6 hours. After filtering through Celite and evaporating the solvent, the obtained crude product was mixed with 12 g of potassium t-butoxide in 280 mL of DMF.
Refluxed for 5 hours. After cooling to room temperature, 300 mL of water was added, and the mixture was extracted with toluene, washed with water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The concentrate obtained by distilling off the solvent was refluxed in 250 mL of a 48% aqueous solution of hydrobromic acid and 250 mL of acetic acid for 5 hours, cooled to room temperature, and poured into 400 mL of ice water. The mixture was extracted with toluene, washed with water, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline in this order, and dried over anhydrous magnesium sulfate. The concentrate obtained by evaporating the solvent was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2- [2- (trans-
42.6 g of 4-propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4-hydroxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene were obtained.

(8-e) 2- [2- (trans-4-
Synthesis of propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene Hydrogen while cooling in an ice-water bath 1.7 g of sodium chloride
The suspension was suspended in 5 mL of HF, and 2- (2-d) obtained in (8-d) was added thereto.
[2- (trans-4-propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4
-Hydroxyphenyl) cyclohexyl] -1,2,2
THF solution of 20 g of 3,4-tetrahydronaphthalene 8
0 mL was added dropwise. After stirring for 1 hour, 30 mL of a THF solution of 8.5 g of -S-ethyl chlorodithiocarbonate was added dropwise. After stirring for 1 hour, the reaction was stopped by adding 20 mL of water, 100 mL of ethyl acetate was added, the organic layer was further washed twice with 40 mL of water, and then dried over anhydrous sodium sulfate and dried. Subsequently, the solvent was distilled off under reduced pressure, and the concentrate obtained was dissolved in 100 mL of dichloromethane, and 350 g of a hydrogen fluoride-melamine complex and 57.8 g of 1,3-dibromo-5,5-dimethylhydantoin cooled to 0 ° C. 1L of
It was added dropwise to the dichloromethane solution. After stirring for 30 minutes,
The reaction was stopped by adding 200 mL of water, and the organic layer was further added with water 1.
After washing twice with 00 mL, it was dehydrated and dried with anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (developing solvent: hexane). This total amount is T
It was dissolved in 100 mL of HF, and 50 mL of a 1.6 M butyllithium hexane solution was added dropwise at -78 ° C. After dripping 1
Stir for 0 min and add 10 mL of water. After returning to room temperature, 20 mL of water was further added. The organic layer was further extracted with 20 mL of water
After repeated washing, the resultant was dehydrated and dried with anhydrous sodium sulfate. Purified by silica gel column chromatography (hexane-ethyl acetate), and recrystallized from ethanol to give 2-
[2- (trans-4-propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4
-Trifluoromethoxyphenyl) cyclohexyl]-
15.0 g of 1,2,3,4-tetrahydronaphthalene was obtained.

The following compounds were obtained in the same manner. 2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3
4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3
4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4- (4
-Trifluoromethoxyphenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans- 4- (4
-Trifluoromethoxyphenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [ Transformer
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2 , 3,4-Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3-fluoro-4-trifluoromethoxyphenyl)
Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4-
(3-fluoro-4-trifluoromethoxyphenyl)
Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3-fluoro-4-trifluoromethoxyphenyl)
Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3-fluoro-4
-Trifluoromethoxyphenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3-fluoro-
4-trifluoromethoxyphenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3-fluoro-4
-Trifluoromethoxyphenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3-fluoro-
4-trifluoromethoxyphenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4- (3
-Fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [ Trans-4-
(3-fluoro-4-trifluoromethoxyphenyl)
Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4- (3
-Fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [ Trans-4-
(3-fluoro-4-trifluoromethoxyphenyl)
Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1 , 2,3,4-
Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl]- 5,7
-Difluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] −5,7−
Difluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl]- 5,7
-Difluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluoro Phenyl) ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1 , 2,3,4-
Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(2,3-Difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl]- 5,7
-Difluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] −5,7−
Difluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl]- 5,7
-Difluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluoro Phenyl) ethyl] -5,7-difluoro-6- [trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro -6- [trans-4-
(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5 , 7-Difluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6-
[Trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4- Butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl ) Ethyl] -5,7,
8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(4-Trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro- 6- [Transformer-4
-(4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6 − [Trans-
4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7,8-tri Fluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl]- 5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6 -Difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1, , 3,4-Tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) ) Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro- 6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2) 3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4- Tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6-
[Trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( Trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( 4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] −5
7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) Ethyl] -5,7,
8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] −5
7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2 -Fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(3-Fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8 -Trifluoro-6- [trans-4
-(3-Fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7 , 8-Trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2, 6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2 -[2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro- -Trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6 [Trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl]- 5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl -2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethyl [Xyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4 -(3-Fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7, 8-trifluoro-6- [trans-4- (3-fluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6-
[Trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2 -(Trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2 -(4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) Ethyl] -5
7,8-trifluoro-6- [trans-4- (3,5
-Difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) Ethyl] -5
7,8-trifluoro-6- [trans-4- (3,5
-Difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro- 6- [Transformer-4
-(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7, 8-trifluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7 , 8-trifluoro-6- [trans-4
-(3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7, 8-trifluoro-6- [trans-
4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5 , 7,8-Trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6
[Trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2 -(Trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2 -(4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) Ethyl] -5
7,8-trifluoro-6- [trans-4- (2,3
-Difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) Ethyl] -5
7,8-trifluoro-6- [trans-4- (2,3
-Difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro- 6- [Transformer-4
-(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7, 8-trifluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7 , 8-trifluoro-6- [trans-4
-(2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7, 8-trifluoro-6- [trans-
4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5 , 7,8-Trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxyphenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-trifluoromethoxy) Phenyl) cyclohexyl] -1,2,3,4-
Tetrahydronaphthalene

Example 9 2- [2- (trans-4-)
Synthesis of propylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

[0357]

Embedded image

The 2- [2- (trans-4-propylcyclohexyl) ethyl] -5,7- obtained in the above (8-d)
25.2 g of triflate was obtained from 20 g of difluoro-6- [trans-4- (4-hydroxyphenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene in the same manner as in the above (2-b). Next, the whole amount was dissolved in 100 mL of acetonitrile, and 1.2 g of dibromobis (triphenylphosphine) nickel (II), 1.0 g of triphenylphosphine, 0.2 g of zinc powder, and 6.1 g of potassium cyanide were added, and the mixture was heated at 80 ° C. for 16 hours. The mixture was heated and stirred. The reaction was stopped by adding 50 mL of water, and toluene 800
mL was added. The organic layer was further washed twice with 50 mL of water, and then dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (hexane-ethyl acetate) and recrystallization from ethanol to give 2- [2-
(Trans-4-propylcyclohexyl) ethyl]-
10.2 g of 5,7-difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene was obtained.

The following compounds were obtained in the same manner. 2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-4- (4
-Cyanophenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4- (4
-Cyanophenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7-difluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3 , 4-Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [trans- 4-
(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3-fluoro-4
-Cyanophenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3-fluoro-
4-cyanophenyl) cyclohexyl] -1,2,3,
4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3-fluoro-4
-Cyanophenyl) cyclohexyl] -1,2,3,4
-Tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3-fluoro-
4-cyanophenyl) cyclohexyl] -1,2,3,
4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4- (3
-Fluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [ Trans-4- (3
-Fluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2 , 3,4-Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [ Trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7-difluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2 , 3,4-Tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7-difluoro-6- [ Trans-4-
(2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7-difluoro-6- [trans-4-
(2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7-
Difluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5,7
-Difluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7-difluoro-6- [trans-4-
(2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7-difluoro-6 − [Trans-4-
(2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7-difluoro -6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7 -Difluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6-
[Trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7 ,
8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(4-cyanophenyl) cyclohexyl] -1,2,2.
3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(4-cyanophenyl) cyclohexyl] -1,2,2.
3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyanophenyl) Cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (4-cyano Phenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6
[Trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans- 4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4- Ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,2
3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,
2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8-tri Fluoro-6- [trans-4
-(3-Fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro -6- [trans-
4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7,8 -Trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,6-difluorophenyl) ) Ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4 -Butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1, , 3,4-Tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4- Cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans- 4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluorophenyl) ethyl] -5,7,8 -Trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2 3-Difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [ 2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3-fluoro-4-cyanophenyl) cyclohexyl] -1,2,2 3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6
[Trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( Trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( 4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (3,5
-Difluoro-4-cyanophenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (3,5
-Difluoro-4-cyanophenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(3,5-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8 -Trifluoro-6- [trans-4
-(3,5-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7 , 8-Trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2, 6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2 -[2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- ( 3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluoro Phenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetra Dronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (3,5-difluoro-4-cyanophenyl) Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- ( 3,5-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

2- [2- (trans-4-ethylcyclohexyl) ethyl] -5,7,8-trifluoro-6-
[Trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-propylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( Trans-4-butylcyclohexyl) ethyl] -5,7,8-trifluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (trans-4-pentylcyclohexyl)
Ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- ( 4-ethylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-propylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (2,3
-Difluoro-4-cyanophenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-butylphenyl) ethyl] -5,7,
8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl]-
1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentylphenyl) ethyl] -5
7,8-trifluoro-6- [trans-4- (2,3
-Difluoro-4-cyanophenyl) cyclohexyl]
-1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2-fluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4
-(2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-butyl-2-fluorophenyl) ethyl] -5,7,8 -Trifluoro-6- [trans-4
-(2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2-fluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-
4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,6-difluorophenyl) ethyl] -5,7 , 8-Trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2, 6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2 -[2- (4-butyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,6-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- ( 2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-ethyl-2,3-difluorophenyl) ethyl] -5,7,8- Trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-propyl-2,3-difluoro Phenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetra Dronaphthalene 2- [2- (4-butyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- (2,3-difluoro-4-cyanophenyl) Cyclohexyl] -1,2,3,4-tetrahydronaphthalene 2- [2- (4-pentyl-2,3-difluorophenyl) ethyl] -5,7,8-trifluoro-6- [trans-4- ( 2,3-Difluoro-4-cyanophenyl) cyclohexyl] -1,2,3,4-tetrahydronaphthalene

Example 10 2-propyl-6- [4-
(3-buten-1-yl) phenyl] -1,2,3,4
Synthesis of tetrahydronaphthalene

[0368]

Embedded image

[0370] 10 g of 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate obtained in the above (2-b) and 0.4 g of tetrakis (triphenylphosphine) nickel (0) were obtained. THF4
To a 0 mL solution, a THF solution of a Grignard reagent prepared from 7.2 g of 4- (3-buten-1-yl) bromobenzene and 0.9 g of magnesium was added dropwise. After stirring for 4 hours, 50 mL of water was added, and extracted with 50 mL of toluene.
The extract was washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was purified by silica gel column chromatography (hexane), and further recrystallized three times from ethanol to give 2-propyl-6- [4- (3-butene-1).
-Yl) -phenyl] -1,2,3,4-tetrahydronaphthalene (7.3 g) was obtained.

The following compounds were obtained in the same manner. 2-ethyl-6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-propyl-6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-butyl-6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-vinyl-6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-ethylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-ethylphenyl)
-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-ethylphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6 (4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4- (Pentylphenyl) -6- (4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
(4-ethylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-ethylphenyl) -1,2,3 , 4
-Tetrahydronaphthalene

2-Ethyl-6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-propylphenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-propylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-propylphenyl) -1,
2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-propylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-propylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-propylphenyl) -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-propylphenyl) -1, 2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) Phenyl] -6-
(4-Propylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-propylphenyl) -1,2,3 ,
4-tetrahydronaphthalene

2-Ethyl-6- (4-butylphenyl)
-1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-butylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-butyl-6- (4-butylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-butylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-vinyl-6- (4-butylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-butylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-butylphenyl)
-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-butylphenyl)
-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6 (4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4- (Pentylphenyl) -6- (4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
(4-butylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-butylphenyl) -1,2,3 , 4
-Tetrahydronaphthalene

2-Ethyl-6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-pentylphenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-pentylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-pentylphenyl) -1,
2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-pentylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-pentylphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-pentylphenyl) -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-pentylphenyl) -1, 2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) Phenyl] -6-
(4-pentylphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-pentylphenyl) -1,2,3 ,
4-tetrahydronaphthalene

2-Ethyl-6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-ethoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-ethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- (4-ethoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-ethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-ethoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-)
Yl) cyclohexyl] -6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-ethoxyphenyl) -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-ethoxyphenyl) -1, 2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) Phenyl] -6-
(4-ethoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-ethoxyphenyl) -1,2,3 ,
4-tetrahydronaphthalene

2-ethyl-6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-propoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-propoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-propoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-propoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans -3-penten-1-yl) -6- (4
-Propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-propoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-)
Yl) cyclohexyl] -6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-propoxyphenyl) -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-propoxyphenyl) -1, 2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) Phenyl] -6-
(4-propoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-propoxyphenyl) -1,2,2
3,4-tetrahydronaphthalene

2-Ethyl-6- (4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-butyroxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-butyl-6- (4-butoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-butyloxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-butoxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-butoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (Trans-3-penten-1-yl) -6- (4
-Butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-Butoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-butyroxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-butyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-butyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-butyroxyphenyl) -1,2,3 4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-butyroxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-butyroxyphenyl ) -1,2,3,4-Tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-butoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-butene -1-yl) phenyl] -6
(4-Butoxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-butoxyphenyl) -1,2 ,
3,4-tetrahydronaphthalene

2-Ethyl-6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2-propyl-6- (4-pentyloxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2-butyl-6- (4-pentyloxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2-pentyl-6- (4-pentyloxyphenyl)-
1,2,3,4-tetrahydronaphthalene 2-vinyl-6- (4-pentyloxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- (4
-Pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (Trans-3-penten-1-yl) -6- (4
-Pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- (4-pentyloxyphenyl) -1,
2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- (4-pentyloxyphenyl) -1,2,3 4-tetrahydronaphthalene 2- (4-propylphenyl) -6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- (4-pentyloxyphenyl ) -1,2,3,4-Tetrahydronaphthalene 2- (4-pentylphenyl) -6- (4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (3-butene -1-yl) phenyl] -6
(4-pentyloxyphenyl) -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- (4-pentyloxyphenyl) -1,2 ,
3,4-tetrahydronaphthalene

2-ethyl-6- [4- (3-butene-1)
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-butyl-6- [4- (3-buten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-pentyl -6- [4- (3-Buten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- [4- (3-buten-1-yl) phenyl] -1 , 2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- [4
-(3-buten-1-yl) phenyl] -1,2,3,3.
4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- [4- (3-buten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-3- Penten-1-yl) -6- [4
-(3-buten-1-yl) phenyl] -1,2,3,3.
4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- [4- (3-buten-1-yl) phenyl] -1,2,3,4- Tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- [4- (3-butene-1
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- [4- (3-butene-1
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- [4- (3-buten-1-yl) phenyl] -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- [4- (3-buten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- [ 4- (3-buten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- [4- (3-buten-1-yl) phenyl]- 1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
[4- (3-buten-1-yl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- [4- (3-buten-1-yl) phenyl] -1,2,3,4- Tetrahydronaphthalene

2-Ethyl-6- [4- (trans-3-
Penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-propyl-6- [4- (trans-3-pentene-
1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-butyl-6- [4- (trans-3-pentene-1
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- [4- (trans-3-pentene-
1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- [4- (trans-3-pentene-1
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- [4
-(Trans-3-penten-1-yl) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- [4- (trans-3-penten-1-yl) phenyl] -1,2,3
4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- [4
-(Trans-3-penten-1-yl) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- [4 -(Trans-3-pentene-1
-Yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- [4- (trans-3-
Penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-penten-1-
Yl) cyclohexyl] -6- [4- (trans-3-
Penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- [4- (trans-
3-penten-1-yl) phenyl] -1,2,3,4
-Tetrahydronaphthalene 2- (4-propylphenyl) -6- [4- (trans-3-penten-1-yl) phenyl] -1,2,3
4-tetrahydronaphthalene 2- (4-butylphenyl) -6- [4- (trans-
3-penten-1-yl) phenyl] -1,2,3,4
-Tetrahydronaphthalene 2- (4-pentylphenyl) -6- [4- (trans-3-penten-1-yl) phenyl] -1,2,3
4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
[4- (trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- [4 -(Trans-3-penten-1-yl) phenyl] -1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- [4- (3-butene-1)
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-propyl-6- [4- (3-buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-butyl -6- [4- (3-Buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- [4- (3-buten-1-yloxy) phenyl] -1 2,2,3,4-tetrahydronaphthalene 2-vinyl-6- [4- (3-buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propene-1 -Yl) -6- [4
-(3-buten-1-yloxy) phenyl] -1,
2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- [4- (3-buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- ( Trans-3-penten-1-yl) -6- [4
-(3-buten-1-yloxy) phenyl] -1,
2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- [4- (3-buten-1-yloxy) phenyl] -1,2,2 3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- [4- (3-butene-1
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- [4- (3-butene-1
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- [4- (3-buten-1-yloxy) phenyl] -1,2,3,4- Tetrahydronaphthalene 2- (4-propylphenyl) -6- [4- (3-buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- [ 4- (3-buten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- [4- (3-buten-1-yloxy) phenyl]- 1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
[4- (3-Buten-1-yloxy) phenyl]-
1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- [4- (3-buten-1-yloxy) phenyl] -1,2,2 3,4-tetrahydronaphthalene

2-Ethyl-6- [4- (trans-3-
Penten-1-yloxy) phenyl] -1,2,3,
4-tetrahydronaphthalene 2-propyl-6- [4- (trans-3-pentene-
1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-butyl-6- [4- (trans-3-pentene-1
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-pentyl-6- [4- (trans-3-pentene-
1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- [4- (trans-3-pentene-1
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- [4
-(Trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- [4- (trans-3-penten-1 -Yloxy) phenyl] -1,
2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- [4
-(Trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- [4 -(Trans-3-pentene-1
-Yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-)
Yl) cyclohexyl] -6- [4- (trans-3-
Penten-1-yloxy) phenyl] -1,2,3,
4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- [4- (trans-3-
Penten-1-yloxy) phenyl] -1,2,3,
4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- [4- (trans-
3-penten-1-yloxy) phenyl] -1,2,2.
3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- [4- (trans-3-penten-1-yloxy) phenyl] -1,
2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- [4- (trans-
3-penten-1-yloxy) phenyl] -1,2,2.
3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- [4- (trans-3-penten-1-yloxy) phenyl] -1,
2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
[4- (trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- [4 -(Trans-3-penten-1-yloxy) phenyl] -1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- [4- (trans-4-
Vinylcyclohexyl) phenyl] -1,2,3,4-
Tetrahydronaphthalene 2-propyl-6- [4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-butyl-6- [4- (trans-4-vinylcyclohexyl) phenyl ] -1,2,3,4-Tetrahydronaphthalene 2-pentyl-6- [4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2-vinyl-6- [4 -(Trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- [4
-(Trans-4-vinylcyclohexyl) phenyl]
-1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- [4- (trans-4-vinylcyclohexyl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- [4
-(Trans-4-vinylcyclohexyl) phenyl]
-1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
[4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6-
[4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
[4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
[4- (Trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
[4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- [4- (trans -4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- [4- (trans-4-
Vinylcyclohexyl) phenyl] -1,2,3,4-
Tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- [4- (trans-4-
Vinylcyclohexyl) phenyl] -1,2,3,4-
Tetrahydronaphthalene 2- (4-ethylphenyl) -6- [4- (trans-
4-vinylcyclohexyl) phenyl] -1,2,3,
4-tetrahydronaphthalene 2- (4-propylphenyl) -6- [4- (trans-4-vinylcyclohexyl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- [4- (trans-
4-vinylcyclohexyl) phenyl] -1,2,3,
4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- [4- (trans-4-vinylcyclohexyl) phenyl] -1,2,2
3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6-
[4- (trans-4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- [4- (trans -4-vinylcyclohexyl) phenyl] -1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- {4- [trans-4-
(Trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2-propyl-6- {4- [trans-4- (trans-1-propen-1-yl) ) Cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2-butyl-6- {4- [trans-4- (trans-
1-propen-1-yl) cyclohexyl] phenyl
-1,2,3,4-tetrahydronaphthalene 2-pentyl-6- {4- [trans-4- (trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydro Naphthalene 2-vinyl-6- {4- [trans-4- (trans-
1-propen-1-yl) cyclohexyl] phenyl
-1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- {4
-[Trans-4- (trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- {4- [ Trans-4- (trans-1-propen-1-yl) cyclohexyl] phenyl {-1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- {4
-[Trans-4- (trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6-
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- {4- [trans-4- (trans-
1-propen-1-yl) cyclohexyl] phenyl
-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(Trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(Trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- {4- [trans-
4- (trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- {4- [trans-4- (trans- 1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- {4- [trans-
4- (trans-1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- {4- [trans-4- (trans- 1-propen-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
{4- [trans-4- (trans-1-propene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- {4- [trans-4- (trans-1-
Propen-1-yl) cyclohexyl] phenyl}-
1,2,3,4-tetrahydronaphthalene

2-Ethyl-6- {4- [trans-4-]
(3-buten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2-propyl-6- {4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,2
3,4-tetrahydronaphthalene 2-butyl-6- {4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,2
3,4-tetrahydronaphthalene 2-pentyl-6- {4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,2
3,4-tetrahydronaphthalene 2-vinyl-6- {4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,2
3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- {4
-[Trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalen 2- (3-buten-1-yl) -6- {4- [trans- 4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- {4
-[Trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6-
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- {4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,2.
3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(3-buten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-pentene-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(3-buten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- {4- [trans-
4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- {4- [trans-4- (3-buten- 1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- {4- [trans-
4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- {4- [trans-4- (3-buten- 1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
{4- [trans-4- (3-buten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- {4- [trans-4- (3-butene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene

2-Ethyl-6- {4- [trans-4-]
(Trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2-propyl-6- {4- [trans-4- (trans-3-penten-1-yl) ) Cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2-butyl-6- {4- [trans-4- (trans-
3-penten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2-pentyl-6- {4- [trans-4- (trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydro Naphthalene 2-vinyl-6- {4- [trans-4- (trans-
3-penten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2- (trans-1-propen-1-yl) -6- {4
-[Trans-4- (trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (3-buten-1-yl) -6- {4- [ Trans-4- (trans-3-penten-1-yl) cyclohexyl] phenyl {-1,2,3,4-tetrahydronaphthalene 2- (trans-3-penten-1-yl) -6- {4
-[Trans-4- (trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-butylcyclohexyl) -6
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-pentylcyclohexyl) -6-
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-ethylcyclohexyl) -6-
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- (trans-4-vinylcyclohexyl) -6-
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- [trans-4- (3-buten-1-yl) cyclohexyl] -6- {4- [trans-4- (trans-
3-penten-1-yl) cyclohexyl] phenyl}
-1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-1-propene-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(Trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [trans-4- (trans-3-penten-1-
Yl) cyclohexyl] -6- {4- [trans-4-
(Trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-ethylphenyl) -6- {4- [trans-
4- (trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-propylphenyl) -6- {4- [trans-4- (trans- 3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-butylphenyl) -6- {4- [trans-
4- (trans-3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- (4-pentylphenyl) -6- {4- [trans-4- (trans- 3-penten-1-yl) cyclohexyl] phenyl} -1,2,3,4-tetrahydronaphthalene 2- [4- (3-buten-1-yl) phenyl] -6
{4- [trans-4- (trans-3-pentene-1)
-Yl) cyclohexyl] phenyl} -1,2,3,4
-Tetrahydronaphthalene 2- [4- (trans-3-penten-1-yl) phenyl] -6- {4- [trans-4- (trans-3-
Penten-1-yl) cyclohexyl] phenyl}-
1,2,3,4-tetrahydronaphthalene

(Example 11) Preparation of liquid crystal composition General-purpose host liquid crystal (H) having a wide temperature range, low viscosity, and usable for active matrix driving

[0387]

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Was prepared. This (H) shows a nematic phase at 116.7 ° C. or lower, and its melting point is + 11 ° C.
Physical properties of this composition and T
The measured values of the electro-optical characteristics of the N cell (cell thickness: 6 μm) at 20 ° C. were as follows.

Threshold voltage (Vth): 2.14 V Dielectric constant anisotropy (Δε): 4.8 Response time (τr = τd): 25.3 ms Refractive index anisotropy (Δn): 0.090 The response time is a measured value when a voltage is applied so that the rise time (τr) and the fall time (τd) are equal.

Next, 80% of the host liquid crystal (H) and the tetrahydronaphthalene compound (I-3) of the present invention obtained in Example 3 were obtained.

[0391]

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When a liquid crystal composition (M-1) consisting of 20% was prepared, the maximum temperature of the nematic phase (T _NI ) was 11%.
8.1 ° C. Further, the crystal was cooled and crystallized, and its melting point (T _CN ) was −3 ° C. Therefore, it is understood that the compound has excellent liquid crystallinity and excellent solubility in the host liquid crystal (H), and can exhibit a liquid crystal phase in an extremely wide temperature range. After heating this (M-1) to 150 ° C. and allowing it to stand for 20 hours, its T _NI was measured. As a result, there was almost no change at 91.5 ° C. as compared to before heating. In addition, UV irradiation (1200 Jm ^-2 s ^-1 ) was applied for 20 hours, but T _NI
Did not change.

Next, when the voltage holding ratio of this composition was measured, it showed a sufficiently high value at the time of preparation, after heating and after irradiation with ultraviolet rays, similarly to the host liquid crystal (H).

Next, (M-1) was converted to a T cell having a cell thickness of 6.0 μm.
A liquid crystal element was prepared by filling in an N cell, and its electro-optical properties were measured. The results were as follows.

Threshold voltage (Vth): 1.92 V Dielectric anisotropy (Δε): 5.5 Response time (τr = τd): 34.2 ms Refractive index anisotropy (Δn): 0.100 By adding 20% of (I-3), the nematic phase temperature range is widened by 15.4 ° C. and the dielectric anisotropy is increased while the response time is also suppressed to 8.9 ms. Vth) could be reduced by 0.22V. Further, the refractive index anisotropy could be increased by 0.01.

(Comparative Example 1) In Example 11, (I-
In place of 3), transdecalin derivative (D-1)

[0397]

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Was added to (H) in the same amount (20%) to prepare a liquid crystal composition (HD-1). The maximum temperature of the nematic phase (T _NI ) of this composition was increased to 122.8 ° C., but the melting point was + 2 ° C., which was higher than (M−1).

The other physical properties of this composition and the electro-optical properties of the device fabricated in the same manner are as follows.

Threshold voltage (Vth): 1.97 V Dielectric anisotropy (Δε): 4.8 Response time (τr = τd): 41.3 ms Refractive index anisotropy (Δn): 0.088 Compared with (I-3), although the maximum temperature of the nematic phase (T _NI ) and the temperature range of the nematic phase are hardly changed, there is no effect of increasing the dielectric anisotropy and the threshold voltage (Vth) The effect of reducing is small. Also,
It can be seen that the response time has increased and the response has deteriorated. Furthermore, the refractive index anisotropy is rather smaller than that of the host liquid crystal (H).

(Comparative Example 2) In Example 11, (I-
In place of 3), the following naphthalene derivative (N-1)

[0402]

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Was added to (H) in the same amount (20%) to prepare a liquid crystal composition (HN-1). This composition has a maximum nematic phase temperature (T _NI ) of 118.6 ° C. and a melting point of −3 ° C.
And had the same temperature characteristics as (I-3).

The other physical properties of this composition and the electro-optical properties of the device fabricated in the same manner are as follows.

Threshold voltage (Vth): 1.97 V Dielectric anisotropy (Δε): 5.4 Response time (τr = τd): 41.4 ms Refractive index anisotropy (Δn): 0.114 Compared with (I-3), the effect of reducing the threshold voltage (Vth) despite the fact that the effect of increasing the maximum temperature of the nematic phase (T _NI ) and the temperature range of the nematic phase and the anisotropy of the dielectric constant hardly change. Is small. In addition, it can be seen that the response time is greatly increased, and the response is deteriorated.

Example 12 Preparation of Liquid Crystal Composition (2) A liquid crystal composition (M) having the following composition was prepared.

4% by weight of 4-ethoxy-1- (trans-4-propylcyclohexyl) benzene 3% by weight of 4-methylphenyl trans-4-pentylcyclohexanecarboxylate 3% by weight of trans-4-propylcyclohexanecarboxylic acid 4-ethoxyphenyl 3% by weight of trans-4- (4-methylphenyl) -trans-4'-vinylbicyclohexane-trans-3% by weight of trans-4-butyl-trans-4'-propylbicyclohexane-trans 4% by weight of trans-4-pentyl-trans-4'-
Vinyl bicyclohexane-trans-3% by weight of 4,4'-bis (3-butenyl) bicyclohexane-trans-4% by weight of 1- (4-propylphenyl) -2- (4-
Methylphenyl) ethyne 3% by weight of 1- (4-ethoxyphenyl) -2- (4-
Pentylphenyl) ethyne 3% by weight of 1,2-bis [4- (3-butenyl) phenyl] ethyne 4% by weight of 1- (4-ethylphenyl) ethynyl-4-
(Trans-4-propylcyclohexyl) benzene 3% by weight of 4- (trans-4-pentylcyclohexyl) -4'-ethylbiphenyl 3% by weight of 4- (trans-4-propylcyclohexyl) -1-cyanobenzene 4% by weight % Of 4- [trans-4- (trans-1-propenyl) cyclohexyl] -1-cyanobenzene 3% by weight of 4- [trans-4- (3-butenyl) cyclohexyl] -1-cyanobenzene 3% by weight 4'-pentyl-4-cyanobiphenyl 4% by weight 2- (4-cyanophenyl) -5-pentylpyrimidine 3% by weight 4-cyanophenyl 4-ethylbenzoate 3% by weight trans-4-pentylcyclohexanecarboxylic acid 3,4-difluorophenyl acid 4% by weight of 3-fluoro-4-cyano 4-butylbenzoate Eniru 3 wt% of 4- (trans-3-penten-1-yl)
3,5-Difluoro-4-cyanophenyl benzoate 3% by weight of trans-4- (3-fluoro-4-cyanophenyl) -trans-4 '-(3-methoxypropyl) bicyclohexane-trans-3% by weight Trans-4- (3,4-difluorophenyl) -trans-4'-ethylbicyclohexane-trans-4% by weight of trans-4- (3,4-difluorophenyl) -trans-4'-vinylbicyclohexane -Trans-4% by weight of trans-4- (3,4,5-trifluorophenyl) -trans-4'-propylbicyclohexane-trans-3% by weight of trans-4- [2- (3,4,4 5-trifluorophenyl) ethyl] -trans-4'-propylbicyclohexane-trans-3% by weight of 4- (trans-4-propyl) Clohexyl) -4'-cyanobiphenyl 4% by weight of 4-fluoro-4-cyanophenyl benzoate 3% by weight of 4 '-(trans-4-propylcyclohexyl) -3, 4,5-trifluorobiphenyl 3% by weight of 1- (3,4,5-trifluorophenyl)
T _NI ethynyl-4- (trans-4-propyl-cyclohexyl) benzene This (M) is 75.0 ° C., [Delta] n is 0.1
42. A liquid crystal composition comprising 90% of this (M) and 10% of the above (I-3) obtained in Example 1 was prepared. The T _NI of this liquid crystal composition was 72.8 ° C., and Δn
Was 0.153.

(Embodiment 13) In the eleventh embodiment, (I
In place of -3), tetrahydronaphthalene compound (I-2) which is the compound of the present invention obtained in Example 2

[0409]

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Was added to (H) in the same amount (20%) to prepare a liquid crystal composition (M-2). Nematic phase maximum temperature (T
_NI ) was 80.9 ° C. It was crystallized by cooling, and its melting point (T _CN ) was + 13 ° C.
After this (M-2) was left at 150 ° C. for 20 hours, its _TNI was measured. As a result, almost no change was observed from that before heating. Irradiation with UV light for 20 hours showed no change in T _NI .

Next, when the voltage holding ratio of this composition was measured, it showed a sufficiently high value as in the case of the host liquid crystal (H) at the time of preparation, after heating and after irradiation with ultraviolet rays.

[0412] Next, (M-2) was converted to a T
A liquid crystal element was prepared by filling in an N cell, and its electro-optical properties were measured. The results were as follows.

Threshold voltage (Vth): 1.64 V Dielectric anisotropy (Δε): 5.3 Response time (τr = τd): 36.5 ms Refractive index anisotropy (Δn): 0.092 By adding (I-2), the dielectric anisotropy was increased, and the threshold voltage (Vth) was significantly reduced by 0.50V.

(Embodiment 14) In the eleventh embodiment, (I
In place of -3), tetrahydronaphthalene compound (I-5) which is the compound of the present invention obtained in Example 5

[0415]

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Was added to (H) in the same amount (20%) to prepare a liquid crystal composition (M-3).

Next, when the voltage holding ratio of this composition was measured, it showed a sufficiently high value as in the case of the host liquid crystal (H) at the time of preparation, after heating and after irradiation with ultraviolet rays.

Next, (M-3) was converted to a T
A liquid crystal element was prepared by filling in an N cell, and its electro-optical properties were measured. The results were as follows.

Threshold voltage (Vth): 1.53 V Dielectric anisotropy (Δε): 5.8 Response time (τr = τd): 36.4 ms Refractive index anisotropy (Δn): 0.090 By adding (I-5), the dielectric anisotropy was increased, and the threshold voltage (Vth) was significantly reduced by 0.61 V.

(Comparative Example 3) In Example 11, (I-
In place of 3), transdecalin derivative (D-2)

[0421]

Embedded image

Was added to (H) in the same amount (20%) to prepare a liquid crystal composition (HD-2). The composition has a maximum nematic phase temperature (T _NI ) of 88.7 ° C. and a melting point of + 13 ° C.
Met.

The other physical properties of this composition and the electro-optical properties of the device fabricated in the same manner are as follows.

Threshold voltage (Vth): 1.69 V Dielectric anisotropy (Δε): 5.7 Response time (τr = τd): 31.0 ms Refractive index anisotropy (Δn): 0.080 Compared with (I-2) and (I-5), the effect of reducing the threshold voltage (Vth) is small. The refractive index anisotropy is smaller than that of the host liquid crystal (H).

(Comparative Example 4) In Example 11, (I-
In place of 3), naphthalene derivative (N-2)

[0426]

Embedded image Was added to (H) in the same amount (20%), and the liquid crystal composition (HN-
2) was prepared. This composition had a maximum nematic phase temperature (T _NI ) of 84.9 ° C. and a melting point of + 2 ° C.

The other physical properties of this composition and the electro-optical properties of the device fabricated in the same manner are as follows.

Threshold voltage (Vth): 1.74 V Dielectric anisotropy (Δε): 5.7 Response time (τr = τd): 31.1 ms Refractive index anisotropy (Δn): 0.107 Compared with (I-2) and (I-5), the effect of reducing the threshold voltage (Vth) is small.

[0429]

The tetrahydronaphthalene derivative provided by the present invention is excellent in liquid crystallinity and compatibility with currently used liquid crystal compounds or compositions. Further, the addition thereof can greatly reduce the threshold voltage without substantially deteriorating the response. Furthermore, as shown in Examples, it is easy to produce industrially, and it is colorless and chemically stable. Therefore, a liquid crystal composition containing the same is extremely useful as a practical liquid crystal, particularly for a liquid crystal display requiring a low temperature drive and a high-speed response over a wide temperature range.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme court ゛ (Reference) C09K 19/32 C09K 19/32 (72) Inventor Yoshitaka Saito 1322-2 Omotijonji, Iwatsuki-shi, Saitama (72 Inventor Haruyoshi Takatsu 3-6-27 Nakahara, Higashiyamato-shi, Tokyo F-term (reference) 4H006 AA01 AA03 AB64 EA36 EA37 GP03 GP20 GP22 4H027 BA01 BB03 BC04 BD01 BD02 BD05 BD07 BD08 BD09 BD24 CB01 CB02 CC04 CD04 CL01 CL04 CM01 CM04 CN01 CN04 CP04 CQ01 CQ04 CT02 CT04 CW01 CW02 DE04 DK01 DK02 DK03 DK04 DK05 DM01 DM02 DM03 DM04 DM05

Claims (13)

[Claims] 1. A compound of the general formula (I) (In the formula, R represents an alkyl group having 1 to 20 carbon atoms, an alkoxyl group, an alkenyl group or an alkenyloxy group, which is an alkoxyl group having 1 to 7 carbon atoms or 1
May be substituted by up to 7 halogen atoms,
m and n are each independently 0 or 1, and rings A, B and C are each independently a trans-1,4-cyclohexylene group or optionally substituted with one or more halogen atoms; , 4-phenylene group, pyridine-
2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group, trans decahydronaphthalene-2,6-diyl group, tetrahydronaphthalene-2,6-diyl group, a naphthalene-2,6-diyl group, L, M and Q -CH ₂ CH ₂ are each independently -, - CH ₂ CH ₂ CH ₂ CH ₂
-, - CH = CH -, - CH = CHCH 2 CH 2 -, - C
_{H 2 CH 2 CH = CH -} , - CH (CH 3) CH 2 -, - C
_{H 2 CH (CH 3) -} , - CF = CF -, - CH 2 O-,
—OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —COO
-, -OCO-, -C≡C- or a single bond;
X ¹ , X ² and X ³ each independently represent a hydrogen atom or a fluorine atom, and Z may be substituted by a hydrogen atom, a halogen atom, a cyano group, a cyanato group, or one or more fluorine atoms Represents an alkyl group, an alkoxyl group, an alkenyl group, or an alkenyloxy group having 1 to 20 carbon atoms. However, when m = 0 and R represents an unsubstituted alkyl group or an alkoxyl group, 1) at least one of X ¹ , X ² and X ³ represents a fluorine atom, and / or 2) ring B or 1,4-phenylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group in which at least one of ring C is substituted by one or more halogen atoms , Pyridazine-3,
6-diyl group, trans-1,3-dioxane-2,5
-Diyl group, transdecahydronaphthalene-2,6-
Represents a diyl group, a tetrahydronaphthalene-2,6-diyl group, a naphthalene-2,6-diyl group, and / or 3) alkyl having 1 to 20 carbon atoms wherein Z is substituted by one or more halogen atoms. group, an alkoxyl group, an alkenyl group, an alkenyloxy group, and / or 4) ₂ Q is -CH when _{n = 0 CH 2 -, -} CF = CF
—, —CF ₂ O—, —OCF ₂ —, —C≡C— and / or 5) When n = 1, at least one of M and Q represents a single bond. A) a tetrahydronaphthalene derivative represented by the formula: 2. The tetrahydronaphthalene derivative according to claim 1, wherein m = 1 in the general formula (I). 3. In the general formula (I), X ¹ , X ² and X
The tetrahydronaphthalene derivative according to claim 1, wherein at least one of ³ is a fluorine atom. 4. The tetrahydronaphthalene derivative according to claim 3, wherein in the general formula (I), at least one of X ¹ and X ² is a fluorine atom. 5. The tetrahydronaphthalene derivative according to claim 1, wherein in the general formula (I), ring C is a 1,4-phenylene group substituted by one or more fluorine atoms. 6. The tetrahydronaphthalene derivative according to claim 1, wherein in the general formula (I), ring C is a trans-1,4-cyclohexylene group substituted by one or more fluorine atoms. 7. In the general formula (I), Q represents —CH ₂ CH ₂
-, - CF = CF -, - CF 2 O -, - OCF 2 -, - C
The tetrahydronaphthalene derivative according to claim 1, which is で C- or a single bond. 8. In the general formula (I), Z is a fluorine atom,
The tetrahydronaphthalene derivative according to claim 1, which is an alkyl group having 1 to 7 carbon atoms, an alkoxyl group, an alkenyl group, or an alkenyloxy group, which is substituted by one or more fluorine atoms. 9. In the general formula (I), R represents 1 carbon atom.
The tetrahydronaphthalene derivative according to claim 1, which is a straight-chain alkyl group or a straight-chain alkoxyl group. 10. A liquid crystal composition containing the compound represented by the general formula (I) according to claim 1. 11. The liquid crystal composition according to claim 10, which is used for driving an active matrix. 12. A liquid crystal device comprising the liquid crystal composition according to claim 10 as a constituent. 13. An active matrix driven liquid crystal display device using the liquid crystal composition according to claim 11.