JP2001039902A - Decahydronaphthalene derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide the subject novel decahydronaphthalene derivative that bears heterocyclic aromatic ring, condensed aromatic ring or the like, has a broad temperature range of the nematic phase with small refractive anisotropy, low-voltage driving, high-speed response and is useful as a liquid crystal composition for STN and TFT driving. SOLUTION: This is a compound represented by formula I (R is a 1-12C alkyl or the like; L is -CH2CH2- or the like, or a single bond; Z is H, a halogen, a 1-12C alkyl or the like; and ring Q is 1,4-phenylene or the like), typically 2-ethoxy-6-(3,4,5-trifluorophenyl)trans-decahydronaphthalene. The compound of formula I is prepared, for example, by reducing the compound of formula II, converting the product to an alcoholate with a base, then etherifying the alcoholate with a compound of the formula: La-Ra (Ra is an alkyl; and La is a halogen such as, chlorine or the like or an eliminating group), deacetalizing to give the compound of the formula III, allowing the product of formula III to react with an organometallic agent IV (Xa-Xc are each H or fluorine; Wa is MgCl or the like; and Za is H or the like), and subjecting the product to dehydration and hydrogenation of the double bond moiety.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a decahydronaphthalene derivative which is a novel liquid crystal compound and a liquid crystal composition containing the same. These are useful for electro-optical liquid crystal displays, particularly as nematic liquid crystal materials having a wide temperature range.

[0002]

2. Description of the Related Art Liquid crystal display elements have been used in various measuring instruments, such as watches and calculators, automobile panels, word processors, electronic organizers, printers, computers, televisions, and the like. Typical liquid crystal display systems are TN (twisted nematic), STN (super twisted nematic), DS (dynamic light scattering), GH (guest-host), and FLC (ferroelectric liquid crystal). ), Etc., and the multiplex drive has been generally used as the drive method instead of the conventional static drive. Further, the simple matrix method, more recently, the active matrix method has been put to practical use.

[0003] In accordance with these display methods and drive methods, various characteristics are required as liquid crystal materials. Above all, a wide temperature range is very important in most cases.This is because the maximum temperature of the nematic phase (T _NI ) is sufficiently high and the melting point (T _CN ) or the smectic-nematic transition temperature ( T _SN ) is sufficiently low.

Also, compatibility with other liquid crystal compounds and general-purpose liquid crystal compositions is important. If the compatibility is poor, it is necessary to mix a very large number of liquid crystal compounds in order to avoid the risk of precipitation or phase separation, and the preparation of the composition requires a great deal of time and cost. I couldn't.

A sufficiently low driving voltage is also an important characteristic in many cases.
(Vth) needs to be low.

Another important characteristic is that the response time is high. Therefore, it is required that the viscosity of the liquid crystal is as small as possible.

The refractive index anisotropy (Δn) is also an important characteristic, and various values are required depending on the display method. However, in the case of a liquid crystal element having a large cell thickness, which is easy to manufacture, it is small. Values are often required.

To meet these demands, a large number of liquid crystal compounds have been synthesized so far, but not all of the problems have been solved, and liquid crystals having better properties for each of the above demands have not been solved. At present, compounds are required.

In general, a liquid crystal compound is structurally formed of a central skeleton (core) and side groups (side chains and polar groups). Examples of the ring structure constituting the core portion include a 1,4-phenylene group (which may be substituted by fluorine) and a trans-1,4-cyclohexylene group, a pyridine-2,5-diyl group and a pyrimidine- Many are already known, such as a heteroaromatic ring such as a 2,5-diyl group and a saturated heterocycle such as a dioxane-trans-1,4-diyl group and a piperidine-1,4-diyl group. However, it is usually almost limited to 1,4-phenylene groups (which may be substituted by fluorine), trans-1,4-cyclohexylene groups and a small number of heteroaromatic rings, and is composed of these ring structures. The fact is that the liquid crystal compound alone cannot sufficiently meet the characteristics required for a liquid crystal composition which is becoming more advanced year by year.

It is known that converting the trans-1,4-cyclohexylene group to a trans-2,6-transdecahydronaphthylene group improves liquid crystallinity. Moreover, since the trans-2,6-transdecahydronaphthylene group is a saturated ring containing no hetero atom such as an oxygen atom or a nitrogen atom, excellent stability can be expected.
However, there have been few examples of trans-2,6-transdecahydronaphthalene derivatives reported so far, and their properties were hardly known.

Recently, we have found that 2- (3,5-difluoro-4-
(A) is a cyanophenyl) -trans-2,6-transdecahydronaphthalene derivative

[0012]

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Or 2- (3,4,5-trifluorophenyl)
-Trans-2,6-transdecahydronaphthalene derivative (B)

[0014]

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And other novel phenyldecahydronaphthalene derivatives having excellent liquid crystallinity and a threshold voltage.
(Vth), and has an excellent effect of reducing the refractive index anisotropy (Δn), expanding the nematic phase temperature range, and has excellent compatibility with other liquid crystal compounds and general-purpose liquid crystal compositions. It was reported that (A) is useful mainly for STN display and (B) is useful mainly for TFT.

On the other hand, in order to improve the liquid crystal properties or electro-optical properties, in addition to the decahydronaphthalene skeleton,
It can be imagined that introducing a ring structure such as a heteroaromatic ring or a condensed aromatic ring would be effective. However, a liquid crystal compound having a heteroaromatic ring, a condensed aromatic ring, or the like having such a skeleton has not been known so far, including its production method.

[0017]

An object of the present invention is to provide a novel liquid crystalline compound which is a decahydronaphthalene derivative having a ring structure such as a heteroaromatic ring or a condensed aromatic ring. With a wide nematic phase temperature range, low refractive index anisotropy, low voltage drive and high-speed response, STN or TFT
Another object of the present invention is to provide a liquid crystal composition suitable for driving.

[0018]

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

[0019]

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(In the formula, R represents an alkyl group having 1 to 12 carbon atoms, an alkoxyl group, an alkenyl group, an alkenyloxy group, an alkanoyloxy group or an alkoxycarbonyl group, or a cyano group, a cyanato group, a hydroxyl group or a carboxyl group; L is -CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , -CH ₂ CH
(CH ₃ )-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -COO-, -OC
O -, - CH = CH - , - CF = CF -, - C≡C -, - O (CH 2) 3 -, - (CH 2) 3 O
-,-(CH ₂ ) ₄ -or a single bond, Z is a hydrogen atom or a halogen atom of fluorine, chlorine, bromine or iodine or an alkyl group having 1 to 12 carbon atoms, an alkoxyl group, an alkenyl group, an alkenyloxy group Represents an alkanoyloxy group or an alkoxycarbonyl group or a cyano group, a cyanato group, a hydroxyl group or a carboxyl group, and ring Q is
1,4-phenylene group, pyrimidine-2,5-diyl group, pyridine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine
-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group, bicyclo [2.2.2] octane-1,4-diyl group, naphthalene-2,6-diyl group, 1,2 , 3,4-tetrahydronaphthalene-2,
Represents a 6-diyl group or a decahydronaphthalene-2,6-diyl group, the decahydronaphthalene ring is in a trans form,
The 2,6-position is in the trans configuration, but when R or Z represents an alkyl group, an alkoxyl group, an alkenyl group, an alkenyloxy group, an alkanoyloxy group or an alkoxycarbonyl group, one or more fluorine atoms or carbon atoms respectively May be substituted by an alkoxyl group of numbers 1 to 7, ring Q may be substituted by one or more fluorine atoms, provided that when ring Q represents a 1,4-phenylene group, R represents an alkoxyl group or Represents an alkenyloxy group and L
Represents a single bond and at least one ring Q is substituted by a fluorine atom, and ring Q is decahydronaphthalene-
When R represents an 2,6-diyl group and R represents an alkyl group and Z represents an alkanoyloxy group, L is not a single bond or -COO-, and ring Q is a decahydronaphthalene-2,6-diyl group. And when R and Z both represent an alkoxyl group or an alkanoyloxy group, L is not a single bond, and ring Q represents a naphthalene-2,6-diyl group and R is an unsubstituted alkyl group or substituted. Ring Q represents a compound which is substituted by at least one fluorine atom when L represents -COO- and does not represent an alkoxyl group. A) a decahydronaphthalene derivative represented by the formula:

2. In the general formula (I), L is -CH ₂ CH _2- , -CH ₂
O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -COO-, -OCO-, -CF = CF-
Or the decahydronaphthalene derivative according to the above 1, which represents a single bond. 3. In general formula (I), ring Q is 1,4-phenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-
2. The decahydronaphthalene derivative according to the above 1, which represents a 2,6-diyl group or a decahydronaphthalene-2,6-diyl group. 4. In the general formula (I), R is an alkyl group having 1 to 12 carbon atoms which may be substituted by one or more fluorine atoms or an alkoxyl group having 1 to 7 carbon atoms, an alkoxyl group, an alkenyl group or an alkenyloxy group. 2. The decahydronaphthalene derivative according to the above 1, which represents 5. In the general formula (I), Z is a hydrogen atom, or fluorine,
A halogen atom of chlorine, bromine or iodine, or an alkyl group having 1 to 12 carbon atoms, an alkoxyl group, an alkenyl group or an alkenyl which may be substituted by one or more fluorine atoms or an alkoxyl group having 1 to 7 carbon atoms. 2. The decahydronaphthalene derivative according to the above 1, which represents an oxy group or a cyano group. 6. The above 1 wherein L in formula (I) represents a single bond.
The decahydronaphthalene derivative according to the above. 7. A liquid crystal composition containing the compound represented by the general formula (I) according to any one of the above 1 to 6. 8. 8. A liquid crystal device comprising the liquid crystal composition according to the above item 7 as a constituent element. Was found as a means for solving the above-mentioned problem.

[0022]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention provides a compound represented by the following general formula (I):

[0023]

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And a decahydronaphthalene derivative represented by the formula:

Wherein R is an alkyl group having 1 to 12 carbon atoms,
Alkoxyl group, alkenyl group, alkenyloxy group,
Alkanoyloxy or alkoxycarbonyl groups
Or cyano, cyanato, hydroxyl or carboxy
Represents at least one fluorine atom or carbon
Even if it is substituted by an alkoxyl group having 1 to 7 atoms.
Often, alkyl groups having 1 to 12 carbon atoms, alkoxyl
Groups, alkenyl groups or alkenyloxy groups are preferred
Straight-chain alkyl group having 1 to 7 carbon atoms, 1 carbon atom
To 6 linear alkoxyl groups or vinyl groups,
S-1-propenyl group, 3-butenyl group, trans-3-pentene
Nil group, trans-2-propenyloxy group, trans-2-
Butenyloxy group, trans-4-pentenyloxy group,
Trans-4-hexenyloxy group, trifluoromethoxy
Si group, difluoromethoxy group, 2-fluoroethenyl group,
2,2-difluoroethenyl group, 2-methoxyethyl group or
A methoxyethoxy group is more preferred, and has 1 to 7 carbon atoms.
Linear alkyl group or vinyl group, trans-1-
Propenyl group, 3-butenyl group, trans-3-pentenyl
Group, 2-fluoroethenyl group or 2,2-difluoroethenyl
Most preferred. L is -CH _TwoCH_Two-, -CH (CH_Three) CH_Two-, -CH
_TwoCH (CH_Three)-, -CH_TwoO-, -OCH_Two-, -CF_TwoO-, -OCF_Two-, -COO-,
-OCO-, -CH = CH-, -CF = CF-, -C≡C-, -O (CH_Two)_Three-,-(CH_Two)
_ThreeO-,-(CH_Two)_Four-Or represents a single bond, but -CH_TwoCH_Two-, -CH_TwoO
-, -OCH_Two-, -CF_TwoO-, -OCF_Two-, -COO-, -OCO-, -CF = CF-
Or a single bond is preferable, and a single bond is more preferable. Z is
Hydrogen atom or fluorine, chlorine, bromine or iodine
A hydrogen atom or an alkyl group having 1 to 12 carbon atoms,
Alkoxyl group, alkenyl group, alkenyloxy group,
Lucanoyloxy group or alkoxycarbonyl group
Or cyano, cyanato, hydroxyl or carboxyl
Represents one or more fluorine or carbon atoms
It may be substituted by an alkoxyl group having 1 to 7 atoms.
Hydrogen, or fluorine, chlorine, bromine or iodine
Halogen atom or alkyl having 1 to 12 carbon atoms
Group, alkoxyl group, alkenyl group or alkenyl group
Xy groups or cyano groups are preferred, and fluorine atoms, chlorine
Atom, linear alkyl group having 1 to 7 carbon atoms or carbon atom
Linear alkoxyl or vinyl group having 1 to 6
Lance-1-propenyl group, 3-butenyl group, trans-3-pe
Tertenyl group, trans-2-propenyloxy group, tolan
S-2-butenyloxy group, trans-4-pentenyloxy
Group, trans-4-hexenyloxy group, trifluoromethyl
Toxyl group, difluoromethoxy group, 2-fluoroethenyl
Group, 2,2-difluoroethenyl group, methoxyethyl group,
A ethoxyethoxy group or a cyano group is more preferred. ring
Q represents a 1,4-phenylene group, a pyrimidine-2,5-diyl group,
Gin-2,5-diyl group, pyrazine-2,5-diyl group, pyridazi
3,6-diyl group, trans-1,3-dioxane-2,5-diyl
Group, bicyclo [2.2.2] octane-1,4-diyl group, naphtha
Len-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-
2,6-diyl group or decahydronaphthalene-2,6-diyl
Represents a 1,4-phenylene group, naphthalene-2,6-diyl
1,2,3,4-tetrahydronaphthalene-2,6-diyl group
Or a decahydronaphthalene-2,6-diyl group is preferred
And each is substituted by one or more fluorine atoms.
May be used to improve the compatibility with other liquid crystal compounds.
If at least one of them is substituted with a fluorine atom
It is preferable to improve liquid crystal properties and high-speed response.
If less than 3 substituted fluorine atoms
Is preferred. The decahydronaphthalene ring is in trans form
And the 2,6-position is in the trans configuration. Where the ring Q is
When representing a 1,4-phenylene group, R is an alkoxyl group or
Represents an alkenyloxy group, L represents a single bond, and
At least one of the 2,3,5,6-positions of the 1,4-phenylene group
Represents a fluorine atom. Further, ring Q is decahydronaphthalene-
Represents an 2,6-diyl group wherein R and Z are unsubstituted;
When L represents a alkyl group, L is not a single bond.

In the general formula (I), various kinds of compounds are included depending on the selection of R, L, Z and the ring Q. Among them, among the general formulas (Iaa) to (Iio ')

[0027]

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[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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[0033]

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[0034]

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[0035]

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The compound represented by the general formula (Ii)
Compounds of a) to (Iio ′) are more preferred, and compounds of general formulas (Iia) to
Compounds of (Iie) or (Iil) to (Iio ') are particularly preferred. Wherein ^Ra is one or more fluorine atoms or 1-3 carbon atoms.
Carbon atoms which may be substituted by the alkoxy group of
Represents an alkyl group or an alkenyl group of 1 to 7, an alkoxy group or an alkenyloxy group, but represents a linear alkyl group or a linear alkoxy group or a vinyl group having 1 to 7 carbon atoms, a trans-1-propenyl group, 3 -Butenyl group, trans-3-pentenyl group, 2-propenyloxy group, trans-2-butenyloxy group, trans-4-pentenyloxy group, trans-4-hexenyloxy group, trifluoromethoxy group, difluoromethoxy group, 2 -Fluoroethenyl, 2,2-difluoroethenyl, 2-methoxyethyl or 2-methoxyethoxy are preferred. Z ^a is 1 or more fluorine atoms or an alkyl group which carbon atoms which may have 1-7 substituents by alkoxy groups having 1 to 3 carbon atoms,
Represents an alkoxyl group, an alkenyl group or an alkenyloxy group or a hydrogen atom, a fluorine atom, a chlorine atom or a cyano group, but is a straight-chain alkyl group or straight-chain alkoxy group or vinyl group having 1 to 7 carbon atoms, trans-1. -
Propenyl group, 3-butenyl group, trans-3-pentenyl group, 2-propenyloxy group, trans-2-butenyloxy group, trans-4-pentenyloxy group, trans-4-hexenyloxy group, trifluoromethoxy group, difluoro A methoxy group, a 2-fluoroethenyl group, a 2,2-difluoroethenyl group, a 2-methoxyethyl group or a 2-methoxyethoxy group, a hydrogen atom, a fluorine atom, a chlorine atom or a cyano group is preferred.

The compound of the general formula (I) has its R, L, Z and ring
The compound can be produced based on the following steps depending on what Q represents (in particular, ring Q), but the production method of the compound of the general formula (I) is not limited to the following production examples.

Method A) wherein R is an alkoxyl group, L is a single bond, Z is a hydrogen atom or a halogen atom of fluorine or chlorine, an alkyl group or an alkoxyl group, and the ring Q is substituted with a fluorine atom. In the case of a 1,4-phenylene group which may be represented by the general formula (IIa)

[0039]

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(Wherein the decahydronaphthalene ring has a trans configuration.) (This compound is described in Japanese Patent Application No. 10-370788.) Can be produced based on the production method), and the alcohol derivative (IIb)

[0041]

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(Wherein the decahydronaphthalene ring has the same meaning as described above), which is converted to an alcoholate with a base, and then converted to a compound of the general formula (IVa).

[0043]

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Table in [0044] (wherein, R ^a represents an alkyl group, L ^a represents a leaving group such as a halogen atom or a p- toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group chlorine, bromine also iodine.) The compound is reacted with a compound to be etherified and then deacetalized to give a decahydronaphthalen-2-one derivative (IIc)

[0045]

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(Wherein ^Ra and the decahydronaphthalene ring have the same meanings as described above). This is represented by the general formula (IIIa)

[0047]

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(Where X is^a, X^bAnd X^cAre independent
Represents a hydrogen atom or a fluorine atom, and W ^aIs MgCl, MgBr,
Metals or metals including MgI, Li, 1 / 2Cu or CuLi
Represents a group, Z^aIs a hydrogen atom or fluorine or chlorine atom
A hydrogen atom or an alkyl or alkoxyl group
Represent. ) (These are the corresponding
It can be easily prepared from a logenated benzene derivative. ) And anti
After dehydration in the presence of an acid catalyst,
Tahydronaphthalene derivative (Va)

[0049]

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[0050] ^{(wherein, R a, X a, X} b, X c, Z a represents the same meaning as in the foregoing, the octahydronaphthalene ring 9,10
-The position is a trance configuration. ). By hydrogenating the double bond portion of the octahydronaphthalene group and, if necessary, isomerizing in the presence of an alkali catalyst, the compound represented by formula (I)
R is an alkoxyl group, L is a single bond, Z is a hydrogen atom or a halogen atom of fluorine or chlorine or an alkyl group or an alkoxyl group,
And a phenyldecahydronaphthalene derivative (Iz) wherein ring Q represents a 1,4-phenylene group which may be substituted with a fluorine atom

[0051]

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[0052] ^{(wherein, R a, X a, X} b, X c, Z a and decahydronaphthalene ring represents the same meaning as in the foregoing.)
Can be manufactured.

Production method b) R is an alkoxyl group, L is a single bond, Z is a halogen atom of bromine or iodine, and ring Q may be substituted with a fluorine atom.
-In the case of a phenylene group, the general formula (Iy) obtained based on the production method a)

[0054]

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(Wherein, R ^a , X ^a , X ^b , X ^c and decahydronaphthalene ring have the same meanings as described above), and are directly brominated or iodinated to a phenyldecahydronaphthalene derivative represented by the formula: Or, after lithiation with alkyllithium, by reacting with bromine or iodine, R in the general formula (I) is an alkoxyl group, L is a single bond, and Z is a halogen atom of bromine or iodine. And a decahydronaphthalene derivative (Ix) in which ring Q represents a 1,4-phenylene group which may be substituted by a fluorine atom

[0056]

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(Wherein L ^b represents a halogen atom of bromine or iodine, and R ^a , X ^a , X ^b , X ^c and the decahydronaphthalene ring have the same meanings as described above). it can.

Production method c) When R is an alkoxyl group, L is a single bond, Z is an alkenyl group, and ring Q is a 1,4-phenylene group which may be substituted with a fluorine atom. General formula (Iw) obtained based on

[0059]

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(Wherein R ^b represents a hydroxyl-protecting group such as a methyl group or a 2-methoxyethoxyethyl group, and R ^a , X ^a ,
X ^b , X ^c and the decahydronaphthalene ring have the same meanings as described above. Deprotection of a phenyldecahydronaphthalene derivative represented by) with hydrobromic acid or the like to give a phenol derivative (Iv)

[0061]

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(Wherein, R ^a , X ^a , X ^b , X ^c and decahydronaphthalene ring have the same meanings as described above), and include p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride. General formula (Iu) obtained by reacting

[0063]

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(Wherein L ^c represents a leaving group such as p-toluenesulfonyloxy group or trifluoromethanesulfonyloxy group, and R ^a , X ^a , X ^b , X ^c and decahydronaphthalene ring are as defined above. Represents the same meaning)) with an organometallic reactant (IVc)

[0065]

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(Wherein, R ^b represents an alkenyl group, W ^b represents MgC
represents a metal such as l, MgBr, MgI, Li, 1 / 2Cu or CuLi, or a metal-containing group. ) And a coupling reaction in the presence of a transition metal catalyst, R in the general formula (I) is an alkoxyl group, L is a single bond, Z is an alkenyl group, and ring Q is substituted with a fluorine atom. May be
A decahydronaphthalene derivative representing a 1,4-phenylene group can be produced. Here, the transition metal catalyst is preferably a palladium complex or a nickel complex.

Alternatively, the compound represented by the general formula (Ix) may be used in place of the compound represented by the general formula (Iu) for etherification in the same manner.

Alternatively, the compound represented by the general formula (Iu) or (Ix) is reacted with N, N-dimethylformamide or o-formate to form a benzaldehyde derivative (It).

[0069]

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(Wherein R ^a , X ^a , X ^b , X ^c and the decahydronaphthalene ring have the same meanings as described above), and if necessary, the Wittig reagent (VIa)

[0071]

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After the reaction, acid hydrolysis is carried out,
By repeating twice, the alkanal derivative (Is)

[0073]

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(Wherein, n represents an integer of 0 or more; R ^a , X ^a , X
^b , ^Xc and the decahydronaphthalene ring have the same meanings as described above. ). Add Wittig reagent (VIb)

[0075]

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(Wherein R ^d represents a hydrogen atom or an alkyl group which may be substituted with one or more fluorine atoms or an alkoxyl group), and then, if necessary, benzenesulfinic acid or the like is added. Acting to isomerize the double bond to the trans conformation,
(Ir)

[0077]

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(Wherein R ^a , R ^d , X ^a , X ^b , X ^c , n and the decahydronaphthalene ring have the same meanings as described above).

Production method d) R is an alkoxyl group, L is a single bond, Z is an alkenyloxy group, and ring Q
Is a 1,4-phenylene group which may be substituted by a fluorine atom.After converting the phenol derivative (Iv) to an alcoholate, the general formula (IVc)

[0080]

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Wherein R ^e represents an alkenyl group, and L ^d represents a halogen atom of chlorine, bromine or iodine or a leaving group such as a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. R in the general formula (I) is an alkoxyl group or an alkenyloxy group, L is a single bond, Z is an alkenyloxy group, and ring Q is fluorine. 1,4- which may be substituted by an atom
A decahydronaphthalene derivative representing a phenylene group can be produced.

Process e) When R is an alkoxyl group, L is a single bond, Z is a cyano group, and ring Q is a 1,4-phenylene group which may be substituted by a fluorine atom, decahydro Organometallic reagents (Iq) prepared by reacting naphthalene derivatives (Ix) with metals such as magnesium or by directly reacting metals such as lithium with decahydronaphthalene derivatives (Iy)

[0083]

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(Where W ^c is MgCl, MgBr, MgI, Li, 1 / 2Cu
Or a metal such as CuLi or a metal-containing group, R ^a ,
X ^a , X ^b , X ^c and decahydronaphthalene ring have the same meanings as described above. ) Is reacted with carbon dioxide to obtain the general formula (Ip)

[0085]

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(Wherein, R ^a , X ^a , X ^b , X ^c and decahydronaphthalene ring have the same meanings as described above). This is converted into an acid halide with a halogenating agent such as thionyl halide, then reacted with ammonia to form an acid amide, and then dehydrated, whereby R in the general formula (I) is an alkoxyl group, and L is a single bond. And a decahydronaphthalene derivative in which Z is a cyano group and ring Q represents a 1,4-phenylene group optionally substituted with a fluorine atom.

Alternatively, instead of the organometallic reactant (Iq), the benzaldehyde derivative (It) is oxidized with an oxidizing agent such as chromic acid to obtain a benzoic acid derivative (Ip). R is an alkoxyl group, L is a single bond, Z is a cyano group, and ring Q is a 1,4-phenylene group which may be substituted with a fluorine atom to produce a decahydronaphthalene derivative You can also.

Alternatively, by reacting a phenyldecahydronaphthalene derivative (Ix) directly with copper (I) cyanide, or by reacting a cyanide such as sodium cyanide or potassium cyanide in the presence of a transition metal catalyst, R in (I) is an alkoxyl group, L is a single bond, Z is a cyano group, and ring Q is a 1,4-phenylene group optionally substituted with a fluorine atom, a decahydronaphthalene derivative Can also be manufactured.

Process f) In the case where L is a single bond and ring Q is a naphthalene-2,6-diyl group which may be substituted by a fluorine atom, 6-substituted transdecahydronaphthalen-2-one (IId)

[0090]

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(Wherein R ^f represents an alkyl group, and the decahydronaphthalene ring has a trans configuration.) (This compound can be produced according to the production method described in DE-A 3150312). Metal reactant (IIIb)

[0092]

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(In the formula, X ^d , X ^e , X ^f , X ^g , X ^h and X ⁱ each independently represent a hydrogen atom or a fluorine atom, and W ^d represents
MgCl, MgBr, MgI, represents a metal or a metal-containing group such as Li, 1 / 2Cu or CuLi, Z ^b represents a halogen atom or an alkyl or alkoxyl group fluorine or chlorine. ) (These can be easily prepared from the corresponding 2-halogenonaphthalene) and then dehydrated in the presence of an acid catalyst to give an octahydronaphthalene derivative (Vb).

[0094]

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Where R ^f , X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ , Z ^b
And the octahydronaphthalene ring has the same meaning as described above. ). Hydrogenation of the alkene, and isomerization in the presence of an alkali catalyst if necessary, whereby in the general formula (I), L is a single bond, and ring Q may be substituted with a fluorine atom. Naphthyldecahydronaphthalene derivative (Io) representing a 6,6-diyl group

[0096]

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(Where R ^f , X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ , Z ^b
And the decahydronaphthalene ring has the same meaning as described above. ) Can be manufactured.

Alternatively, by using transdecahydronaphthalene-2,6-dione monoacetal (IIa) in place of the 6-substituted transdecahydronaphthalen-2-one (IId), a naphthyldecahydronaphthalene derivative can be similarly obtained. Can also be manufactured.

Alternatively, the naphthyldecahydronaphthalene derivative can be similarly produced by using (IIIb) instead of the organometallic reactant (IIIa) in the production method a).

Alternatively, by using (Io) instead of the decahydronaphthalene derivative (Iz) in the production processes b) to e), a decahydronaphthalene derivative can be similarly produced.

Production Method G) When L is a single bond and Ring Q is a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group which may be substituted by a fluorine atom, (1) 6-substitution Transdecahydronaphthalen-2-one (IId) is reduced, and alcohol derivative (IIe)

[0102]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above), and then reacted with a halogenating agent, or p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride. General formula (IIf)

[0104]

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[0105] (wherein, L ^e is chlorine, bromine also represents a leaving group such as a halogen atom or a p- toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group iodine, R ^f and decahydronaphthalene ring as in the aforementioned The same meaning is obtained.) Compound
(IIf) and an organometallic reactant (IIg) by reacting a metal such as magnesium or an alkyl lithium, etc.

[0106]

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[0107] (In the formula, W ^e is MgCl, MgBr, MgI, Li, 1 / 2Cu
Or a metal such as CuLi or a metal-containing group, and R ^f and decahydronaphthalene ring have the same meanings as described above. ) Was prepared, and 1,2,3,4-tetrahydronaphthalen-2-one derivative (IIIc)

[0108]

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(Where X is^j, X^kAnd X^lAre independent
Represents a hydrogen atom or a fluorine atom, and Z ^cIs fluorine or
Chlorine halogen atom or alkyl group or alkoxy
Represents a sil group. ), Followed by dehydration in the presence of an acid catalyst.
By doing, decahydronaphthalene derivative (Vc)

[0110]

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(In the formula, R ^f , X ^j , X ^k , X ¹ , Z ^c and decahydronaphthalene ring have the same meanings as described above.)
Get. By hydrogenating the double bond portion of the octahydronaphthalene ring, tetrahydronaphthalene-2,6-diyl in the general formula (I), wherein L is a single bond and ring Q may be substituted with a fluorine atom. Decahydronaphthalene derivative (In) representing a group

[0112]

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(In the formula, R ^f , X ^j , X ^k , X ¹ , Z ^c and decahydronaphthalene ring have the same meanings as described above.)
Can be manufactured.

Alternatively, by using transdecahydronaphthalene-2,6-dione monoacetal (IIa) instead of the 6-substituted transdecahydronaphthalen-2-one (IId), a decahydronaphthalene derivative can be similarly obtained. It can also be manufactured.

Alternatively, by using (Iq) instead of the decahydronaphthalene derivative (Iz) in the production processes b) to e), a decahydronaphthalene derivative can be similarly produced.

Production method h) When L is a single bond and ring Q is a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group optionally substituted by a fluorine atom (2) Production method In place of the organometallic reactant (IIIb), the organometallic reactant (IIId)

[0117]

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(Where X is^m, XⁿAnd X^oAre independent
Represents a hydrogen atom or a fluorine atom, and W ^fIs MgCl, MgBr,
Metals or metals including MgI, Li, 1 / 2Cu or CuLi
Represents a group, Z^dIs a halogen atom of fluorine or chlorine
Represents an alkyl group or an alkoxyl group. )(They are
The corresponding 6-halogeno-1,2,3,4-tetrahydronaphthalene
Can be easily prepared from ), The presence of an acid catalyst
Octahydronaphthalene derivative
Body (Vd)

[0119]

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(Wherein R ^f , X ^m , X ⁿ , X ^o , Z ^d and the octahydronaphthalene ring have the same meanings as described above). The decahydronaphthalene derivative (Im) is obtained by hydrogenating the double bond portion of the octahydronaphthalene ring and, if necessary, isomerizing in the presence of an alkali catalyst.

[0121]

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(In the formula, R ^f , X ^m , X ⁿ , X ^o , Z ^d and decahydronaphthalene ring have the same meanings as described above.)
Can be manufactured.

Alternatively, the decahydronaphthalene derivative can be similarly obtained by using transdecahydronaphthalene-2,6-dione monoacetal (IIa) instead of the 6-substituted transdecahydronaphthalen-2-one (IId). It can also be manufactured.

Alternatively, decahydronaphthalene derivative (Im) can be used instead of decahydronaphthalene derivative (Iz) in production methods b) to e) to similarly produce a decahydronaphthalene derivative.

[0125] Preparation Li) L is -CH ₂ CH ₂ - After reaction when decahydronaphthalene-2-one (IId) the Wittig reaction agent (VIa), acid hydrolysis, alkali catalyst optionally By isomerizing in the presence, the carbaldehyde derivative (IIh)

[0126]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above), and are further reacted with a Wittig reagent (VIa), followed by acid hydrolysis to give an ethanal derivative. (IIi)

[0128]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above). Alcohol derivative (IIj) reduced by metal hydride etc.

[0130]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above), and are reacted with a halogenating agent or p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride. General formula (IIk)

[0132]

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(In the formula, L ^f represents a halogen atom of chlorine, bromine or iodine or a leaving group such as p-toluenesulfonyloxy group or trifluoromethanesulfonyloxy group, and R ^f and decahydronaphthalene ring are as defined above. The same meaning is obtained.) Compound
(IIk) and an organometallic reactant (IIl) by reacting a metal such as magnesium or lithium or an alkyl lithium, etc.

[0134]

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(Where W ^g is MgCl, MgBr, MgI, Li, 1 / 2Cu
Or a metal such as CuLi or a metal-containing group, and R ^f and decahydronaphthalene ring have the same meanings as described above. ) Is prepared, 1,4-phenylene derivative (IIIe)

[0136]

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(Wherein L ^g represents a halogen atom of chlorine, bromine or iodine or a leaving group such as p-toluenesulfonyloxy group or trifluoromethanesulfonyloxy group, and X ^a , X ^b , X ^c and Z represent Represents the same meaning as described above.) Or naphthalene derivative (IIIf)

[0138]

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(Wherein, L ^g , X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ and Z have the same meanings as described above) or 1,2,3,
4-tetrahydronaphthalene derivative (IIIg)

[0140]

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(Wherein L ^g , X ^j , X ^k , X ^l and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene derivative (IIIh)

[0142]

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(Where L^g, X^m, Xⁿ, X^oAnd Z are as described above.
Has the same meaning as ) A cup in the presence of a transition metal catalyst
By performing a ring reaction, L in the general formula (I) is
-CH_TwoCH _Two-A decahydronaphthalene derivative
Can be manufactured.

Process L) When L is -COO- The carbaldehyde derivative (IIh) is oxidized with chromic acid or the like to give a carboxylic acid derivative (IIm)

[0145]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above). Compound (II
m) and phenol derivative (IIIi)

[0147]

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(Wherein X ^a , X ^b , X ^c and Z have the same meanings as described above) or a naphthol derivative (IIIj)

[0149]

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(Wherein, X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene-2- All derivative (IIIk)

[0151]

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(Wherein, X ^j , X ^k , ^Xl and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalen-6-ol derivative (IIIl)

[0153]

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(Wherein X ^m , X ⁿ , X ^o and Z have the same meanings as described above) by esterification to give a compound of the general formula (I) wherein L represents —COO—. Decahydronaphthalene derivatives can be produced.

Production Method l) When L is —OCO— Alcohol derivative (IIe) and benzoic acid derivative (IIIm)

[0156]

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(Wherein X ^a , X ^b , X ^c and Z have the same meanings as described above) or naphthalene carboxylic acid derivative (IIIn)

[0158]

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(Wherein X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene-2- Carboxylic acid derivative (IIIo)

[0160]

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(Wherein X ^j , X ^k , ^Xl and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene-6-carboxylic acid derivative (IIIp)

[0162]

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(Wherein X ^m , X ⁿ , X ^o and Z have the same meanings as described above) by esterification to give a compound of the general formula (I) wherein L represents —OCO—. Decahydronaphthalene derivatives can be produced.

Production method i) When L is -CH ₂ O- The carbaldehyde derivative (IIh) is reduced with a metal hydride or the like to give an alcohol derivative (IIn)

[0165]

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(Wherein R ^f and decahydronaphthalene ring have the same meanings as described above), and are then reacted with a halogenating agent, or p-toluenesulfonyl chloride or trifluoromethanesulfonic anhydride. General formula (IIo)

[0167]

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(Where L ^h represents a halogen atom of chlorine, bromine or iodine, or a leaving group such as p-toluenesulfonyloxy group or trifluoromethanesulfonyloxy group, and R ^f and decahydronaphthalene ring are as defined above. The same meaning is obtained.) Compound
(IIo) and phenol derivatives (IIIi), naphthol derivatives (II
Ij), 1,2,3,4-tetrahydronaphthalen-2-ol derivative
By reacting the alcoholate prepared from (IIIk) or 1,2,3,4-tetrahydronaphthalene-6-ol derivative (IIIl), in the general formula (I), L is where representing a -CH ₂ O- Decahydronaphthalene derivatives can be produced.

Production Method a) When L is —OCH ₂ — After converting the alcohol derivative (IIe) into an alcoholate, the phenylene derivative (IIIq)

[0170]

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[0171] (wherein, L ⁱ represents a leaving group such as chlorine, bromine, or a halogen atom or a p- toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group ^{iodine, X a, X b, X} c and Z Represents the same meaning as above.) Or naphthalene acid derivative (IIIr)

[0172]

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(Wherein, L ⁱ , X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ and Z have the same meanings as described above), or 1,2,3,
4-tetrahydronaphthalene derivative (IIIs)

[0174]

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(Wherein, L ⁱ , X ^j , X ^k , X ^l and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene derivative (IIIt)

[0176]

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(Wherein L ⁱ , X ^m , X ⁿ , X ^o and Z have the same meanings as described above), whereby L in the general formula (I) is converted to -OCH _2- . The indicated decahydronaphthalene derivative can be prepared.

Production method f) When L is -CF ₂ O- A decahydronaphthalene derivative (In) in which L in the general formula (I) produced by the production method n) is represented by -COO-

[0179]

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(Wherein R ^f , ring Q, Z and decahydronaphthalene ring have the same meanings as described above) with a Lawesson reagent to give a thiocarboxylic acid O-ester derivative (Io)

[0181]

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(Wherein R ^f , ring Q, Z and decahydronaphthalene ring have the same meanings as described above).
By reacting this with a fluorinating agent such as sulfur tetrafluoride, DAST (dimethylaminosulfur trifluoride) or Deoxo-Fluor (di (methoxyethyl) aminosulfur trifluoride),
A decahydronaphthalene derivative in which L in the general formula (I) represents —CF ₂ O— can be produced.

Production method i) When L is -OCF ₂ -A decahydronaphthalene derivative (Ip) in which L in the general formula (I) produced by the production method l) is represented by -OCO-

[0184]

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(Wherein R ^f , ring Q, Z and decahydronaphthalene ring have the same meanings as described above).
Thiocarboxylic acid O-ester derivative (Iq)

[0186]

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(Wherein R ^f , ring Q, Z and decahydronaphthalene ring have the same meanings as described above).
By reacting this with a fluorinating agent such as DAST or Deoxo-Fluor in the same manner as in Production Method Y), it is possible to produce a decahydronaphthalene derivative in which L in the general formula (I) represents -OCF _2-. it can.

[0188] Process data) when L is -CF = CF- organometallic reagents in (IIg), phenyl lithium derivatives where W ^e represents Li (IIp)

[0189]

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(In the formula, R ^f and decahydronaphthalene ring have the same meanings as described above.) The phenyltrifluoroethylene derivative (IIIu)

[0191]

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(Wherein X ^a , X ^b , X ^c and Z have the same meaning as described above) or a naphthyltrifluoroethylene derivative (IIIv)

[0193]

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(Wherein X ^d , X ^e , X ^f , X ^g , X ^h , X ⁱ and Z have the same meanings as described above) or 1,2,3,4-tetrahydronaphthalene-2- Il-trifluoroethylene derivative (IIIw)

[0195]

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[0196] ^{(wherein, X j, X k, X} l and Z are as defined as in the foregoing.) Or 1,2,3,4-tetrahydronaphthalene-6-yl - trifluoroethylene derivative (IIIx)

[0197]

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(Wherein X ^m , X ⁿ , X ^o and Z have the same meaning as described above) to give a compound of the general formula
A decahydronaphthalene derivative in which L in-(I) represents -CF = CF- can be produced.

Specific examples of the representative compound (I) of the present invention thus produced are shown in Table 1.

[0200]

[Table 1]

The excellent effects obtained by adding the compound of the general formula (I) to the liquid crystal composition are as follows.

(I-2) shown in Table 1

[0203]

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A compound of general formula n-type host liquid crystal (H)

[0205]

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To the nematic liquid crystal composition (H-2)
Was prepared, the maximum temperature of the nematic phase (T _NI ) was
67.1 ° C. This (H-2) was allowed to stand at −20 ° C. for 2 weeks, but no crystal precipitation or phase separation was observed. -60 ℃
And the melting point (T _CN ) was measured to be 0.5 ° C.

Next, a liquid crystal device was prepared by filling (H-2) into a TN cell having a cell thickness of 8.0 μm, and its electro-optical characteristics were measured at 20 ° C., and the results were as follows.

Dielectric anisotropy (Δε) 4.2 Threshold voltage (Vth) 1.56 V Response time (τ) 43.0 ms Refractive index anisotropy (Δn) 0.082 On the other hand, physical properties of the host liquid crystal (H) alone are as follows: It is as follows.

Nematic phase upper limit temperature (T _NI ) 72.5 ° C. Dielectric anisotropy (Δε) -1.3 Refractive index anisotropy (Δn) 0.085 Here, the response time is a rise time (τr) and a fall time (τd). Is the response time at the time of applying the voltage, where
The host liquid crystal (H) does not respond to an electric field because it is n-type, but (H)
In -2), the dielectric anisotropy (Δ
ε) increased to 4.2, and a high-speed response of 43.0 ms was possible. In addition, the threshold voltage (Vth) was 1.56 V, which enabled low voltage driving.

On the other hand, a phenyldecahydronaphthalene derivative (R-2) wherein R is an alkyl group in the general formula (I)

[0211]

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Nematic liquid crystal composition by adding 20% to (H)
(H-R2) was prepared. A liquid crystal element was prepared in the same manner, and its electro-optical characteristics were measured. The results were as follows.

Nematic Phase Maximum Temperature (T _NI ) 65.3 ° C. Melting Point (T _CN ) 2.0 ° C. Dielectric Anisotropy (Δε) 4.0 Threshold Voltage (Vth) 1.68 V Response Time (τ) 41.5 ms Refractive Index Anisotropy ( (N) 0.084 (H-R2) has slightly improved response time than (H-2), but T _NI is slightly lower than (H-2) and Vth is about 10% higher than (H-2) .

As described above, the compound (I-2) of the present invention is excellent in nematic liquid crystal properties, and has the characteristics that the addition thereof greatly increases the dielectric anisotropy and enables high-speed response. (R-2) is similar to (R-2), and has a feature that its threshold voltage can be significantly reduced. ) Is better.

Next, (I-1) shown in Table 1

[0216]

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The compound of the formula (J) was used as a host liquid crystal composition (J) having a wide temperature range and low viscosity.

[0218]

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Was added to obtain a liquid crystal composition (J-1). Here, the physical property values of (J) and the electro-optical characteristic values of the liquid crystal element prepared using the same are as follows.

Nematic phase maximum temperature (T _NI ) 116.7 ° C. Threshold voltage (Vth) 2.14 V Dielectric anisotropy (Δε) 4.8 Refractive index anisotropy (Δn) 0.090 Here, the threshold voltage (Vth) is 6.0 It is a value measured at 20 ° C. by enclosing in a μm TN cell.

On the other hand, the physical property values of (J-1) and the electro-optical characteristic values of the liquid crystal element similarly prepared using the same were as follows.

Nematic phase upper limit temperature (T _NI ) 87.0 ° C. Melting point (T _CN ) 8.0 ° C. Threshold voltage (Vth) 1.60 V Dielectric anisotropy (Δε) 5.9 Refractive index anisotropy (Δn) 0.075 Response time (τ) 44.0 ms Therefore, by adding 20% of (I-1), the dielectric anisotropy was increased, and the threshold voltage (Vth) thereof could be reduced by 0.54V. From this value, the dielectric anisotropy of (I-1) alone calculated by extrapolation was a large value of 10.3. Also, (I-
Despite 1) having a phenyl skeleton in the molecule, the refractive index anisotropy of (J-1) was relatively small.

On the other hand, a phenyldecahydronaphthalene derivative (R-1) in which R is an alkyl group in the general formula (I)

[0224]

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(J) was added in the same amount (20% by weight) to obtain a liquid crystal composition.
When (J-R1) was prepared, the melting point (T _CN ) was 13.0 ° C. and (I-1)
Rose compared to. Therefore, it can be seen that the solubility of (R-1) in the host liquid crystal is not so excellent as compared with (I-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) 1.69 V Dielectric anisotropy (Δε) 5.7 Refractive index anisotropy (Δn) 0.080 Response time (τ) 41.5 ms (J-R1), Vth is (J-1) Larger and the response time (J-
1) It is slightly improved.

As described above, the compound (I-1) of the present invention has excellent nematic liquid crystallinity and compatibility, and its addition greatly increases the dielectric anisotropy and enables high-speed response. (R-1) is similar to (R-1), and has a feature that its threshold voltage can be significantly reduced.
Better than -1).

Next, (I-3) shown in Table 1

[0230]

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The compound of formula (J-3) was added to the host liquid crystal composition (J) in an amount of 20% by weight to prepare a liquid crystal composition (J-3). The physical property values of (J-3) and the electro-optical property values of the liquid crystal devices similarly prepared using the same were as follows.

Nematic phase upper limit temperature (T _NI ) 120.3 ° C. Melting point (T _CN ) -10.0 ° C. Threshold voltage (Vth) 2.59 V Dielectric anisotropy (Δε) 3.4 Refractive index anisotropy (Δn) 0.101 Response time (τ 34.8 ms) Therefore, by adding 20% of (I-3), the maximum temperature of the nematic phase (T _NI ) was increased by about 4 ° C., and the melting point (T _CN ) was significantly reduced to −10 ° C.

On the other hand, a cyclohexylnaphthalene derivative (R-3) which is a 1,4-cyclohexylene group in place of the decahydronaphthalene-2,6-diyl group in the general formula (I)

[0234]

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Was added to (J) in the same amount (20% by weight) to give a liquid crystal composition.
When (J-R3) was prepared, the maximum temperature of the nematic phase (T _NI )
Dropped to 104.7 ° C compared to (I-3). The melting point (T _CN )
The temperature increased to 12.0 ° C compared to (I-3). Therefore, it can be seen that the solubility of (R-3) in the host liquid crystal is not so excellent as compared with (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) 2.43 V Dielectric anisotropy (Δε) 3.2 Refractive index anisotropy (Δn) 0.102 Response time (τ) 28.9 ms Therefore, the electro-optical characteristic of (R-3) is (H-3) It turns out that it is almost equivalent to -3).

As described above, the compound (I-3) of the present invention has an advantage in that it has excellent nematic liquid crystallinity and compatibility, and is equivalent to the similar compound (R-3). It is superior to the similar (R-3) in that it has the advantage of extending the nematic phase temperature range by its addition.

Next, (I-4) shown in Table 1

[0240]

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The compound of the formula (J-4) was added to the host liquid crystal composition (J) in an amount of 20% by weight to prepare a liquid crystal composition (J-4). The physical property values of (J-4) and the electro-optical property values of the liquid crystal devices similarly prepared using the same were as follows.

Nematic phase upper limit temperature (T _NI ) 105.7 ° C. Melting point (T _CN ) + 14.2 ° C. Threshold voltage (Vth) 2.10 V Dielectric anisotropy (Δε) 3.8 Refractive index anisotropy (Δn) 0.090 Response time ( τ) 33.5 msec By adding 20% of (I-4), the maximum nematic phase temperature (T _NI ) was reduced by about 11 ° C., and the melting point (T _CN ) was hardly changed.

On the other hand, a bicyclohexylnaphthalene derivative represented by the general formula (I), which is a 1,1′-bicyclohexane-4,4′-diyl group instead of a decahydronaphthalene-2,6-diyl group (R-4)

[0244]

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(J) was added in the same amount (20% by weight) to obtain a liquid crystal composition.
When (J-R4) was prepared, the maximum temperature of the nematic phase (T _NI )
Increased to 139.2 ° C compared to (I-4). The melting point (T _CN )
33.0 ° C and increased compared to (I-4). Therefore, it can be seen that the solubility of (R-4) in the host liquid crystal is not so excellent as compared with (I-4).

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) 2.34 V Dielectric anisotropy (Δε) 4.7 Refractive index anisotropy (Δn) 0.100 Response time (τ) 31.7 ms Therefore, the electro-optical characteristic of (R-4) is (H It turns out that it is almost equivalent to -4).

The compound (I-4) of the present invention does not have a strong polar group in the molecule, can obtain a large specific resistance and a high voltage holding ratio, and can be used as a liquid crystal material for driving an active matrix. Was.

As described above, the compound (I-4) of the present invention has an advantage in that it has excellent nematic liquid crystallinity and compatibility, and is therefore comparable to the similar (R-4). It is superior to the similar (R-4) in that it has the feature of extending the nematic phase temperature range by its addition.

As described above, the compound of the general formula (I) of the present invention has excellent nematic liquid crystallinity and is comparable to a similar decahydronaphthalene derivative in preparing a liquid crystal composition having a wide temperature range. In particular, it is superior to a similar decahydronaphthalene derivative in that it has a low threshold voltage and can be driven at a low voltage.

Therefore, the compound of the general formula (I) can be used as a mixture with other nematic liquid crystal compounds in the form of TN or ST.
It can be suitably used as a liquid crystal material having a wide temperature range and capable of being driven at a low voltage, particularly for an N-type or other field effect display cell. The compound of the formula (I)
Depending on the selection of L, M and Z, it does not have a strong polar group in the molecule, it is easy to obtain large specific resistance and high voltage holding ratio, and it can be used as a component of active matrix driving liquid crystal material 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.

The composition provided by the present invention contains at least one compound represented by the general formula (I) as the 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 (A1)
It consists of the compound represented by (A3).

[0254]

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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 is a 3- to 6-membered cyclic May have a structure, and any -CH _2- present in the group is -O-, -CH =
CH-, -CH = CF-, -CF = CH-, -CF = CF- or -C≡C- may be replaced by any hydrogen atom present in the group is a fluorine atom or trifluoromethoxy It may be substituted by a group, but may be a linear alkyl group having 2 to 7 carbon atoms, a linear 1-alkenyl group having 2 to 7 carbon atoms, a linear 3-alkenyl group having 4 to 7 carbon atoms. Alkenyl group, terminal has 1-3 carbon atoms
Is preferably an alkyl group having 1 to 5 carbon atoms substituted by an alkoxyl group. 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 by a trans-1,4-cyclohexylene group, a transdecahydronaphthalene-trans-2,6-diyl group, and one or more fluorine atoms. 1,4-phenylene group, 1
A naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, a tetrahydronaphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, 1,4-cyclohexenylene group, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, 1,4-cyclohexylene group, transdecahydronaphthalene-trans-2,6-diyl group,
Naphthalene-2,6 which may be substituted by a fluorine atom
-Diyl groups or 1,4-phenylene groups which may be substituted by one or two fluorine atoms are preferred. Especially when ring B is a trans-1,4-cyclohexylene group or a transdecahydronaphthalene-trans-2,6-diyl group,
Ring A is preferably a trans-1,4-cyclohexylene group, and ring C when ring C is a trans-1,4-cyclohexylene group or a transdecahydronaphthalene-trans-2,6-diyl group And ring A is preferably a trans-1,4-cyclohexylene group. In (A3), the 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- ), a 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-, -C
F = 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—, —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 represented by the following formulas (IXa) to (I
Xd).

[0258]

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[0259] In the formula, represents a Y ^a to Y ^o are each independently a hydrogen atom or fluorine atom, in (IXa), at least one of Y ^a and Y ^b is preferably a fluorine atom, (IXb ), At least one of Y ^d , Y ^e or Y ^g
Preferably, each is a fluorine atom, and more preferably, Y ^d is a fluorine atom.

[0260] end group P ^a represents a fluorine atom, a chlorine atom, trifluoromethoxy group, difluoromethoxy group, trifluoromethyl group or difluoromethyl group or 2 or more carbon atoms substituted by fluorine atoms 2 or 3 of alkoxylation Represents a group, an alkyl group, an alkenyl group or an alkenyloxy group, preferably a fluorine atom, a trifluoromethoxy group or a difluoromethoxy group, particularly preferably a fluorine atom.

In (A2), the compound represented by the general formula (I) of the present invention
Are excluded.

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

[0263]

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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 is a 3- to 6-membered cyclic May have a structure, and any -CH _2- present in the group is -O-, -CH =
CH-, -CH = CF-, -CF = CH-, -CF = CF- or -C≡C- may be replaced by any hydrogen atom present in the group is a fluorine atom or trifluoromethoxy It may be substituted by a group, but may be a linear alkyl group having 2 to 7 carbon atoms, a linear 1-alkenyl group having 2 to 7 carbon atoms, a linear 3-alkenyl group having 4 to 7 carbon atoms. Alkenyl group, terminal has 1-3 carbon atoms
Is preferably an alkyl group having 1 to 5 carbon atoms substituted by an alkoxyl group. 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, 1
A naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, a tetrahydronaphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, 1,4-cyclohexenylene group, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group, 1,4-cyclohexylene group, transdecahydronaphthalene-trans-2,6-diyl group,
Naphthalene-2,6 which may be substituted by a fluorine atom
-Diyl groups or 1,4-phenylene groups which may be substituted by one or two fluorine atoms are preferred. Especially when ring E is a trans-1,4-cyclohexylene group or transdecahydronaphthalene-trans-2,6-diyl group,
Ring D is preferably a trans-1,4-cyclohexylene group, and when ring F is a trans-1,4-cyclohexylene group or a transdecahydronaphthalene-trans-2,6-diyl group, the ring D And ring E is preferably a trans-1,4-cyclohexylene group. In addition, the ring in (B3)
D is preferably a trans-1,4-cyclohexylene group.

L^d, L^eAnd L^fIs a linking group,
Independently a single bond, an ethylene group (-CH _TwoCH_Two-), 1,2-Propylene
Len group (-CH (CH_Three) CH_Two-And-CH_TwoCH (CH_Three)-), 1,4-butyl
Group, -COO-, -OCO-, -OCF_Two-, -CF_TwoO-, -CH = CH-, -CH = C
F-, -CF = CH-, -CF = CF-, -C≡C-, -OCH_Two-, -CH_TwoO-, again
Represents -CH = NN = CH-, but a single bond, an ethylene group, -COO-,-
OCF_Two-, -CF_TwoO-, -CF = CF- or -C≡C- is preferred,
In this case, an ethylene group or -COO- is particularly preferred. Also, (B
At least one of them in (2) and that in (B3)
Preferably represents a single bond.

Ring Y is an aromatic ring represented by the following general formulas (IXe) to (I)
Xh).

[0268]

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[0269] In the formula, represents a Y ^{a '~Y o'} are each independently a hydrogen atom or a fluorine atom, that at least one fluorine atom (IXe) in, Y ^{a 'and} Y ^b' Preferably, in (IXf), Y ^{d ′} is preferably a fluorine atom. Terminal group P ^a represents a cyano group (-CN), cyanato group (-OCN)
Or -C 表 す CCN, preferably a cyano group.

In (B2), the compound represented by the general formula (I) of the present invention
Are excluded.

The fourth component has a dielectric anisotropy of about 0.
It is a so-called n-type liquid crystal, and is composed of compounds represented by the following general formulas (C1) to (C3).

[0272]

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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 - , - CH = CF -, - CF = CH-, -CF
= CF- or -C≡C-, and any hydrogen atom present in the group may be replaced by a fluorine atom or a trifluoromethoxy group, but may have 1 to 7 carbon atoms. Linear alkyl group, linear 1-C2-C7
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 a carbon atom having 1 to 3 carbon atoms whose terminal is substituted by an alkoxyl group having 1 to 3 carbon atoms; 5 linear alkyl groups are preferable, and 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 4 carbon atoms.
Particularly preferably, it is a linear 3-alkenyl group of from 7 to 7.

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, or 1 to 2 fluorine atoms May be substituted by atom or methyl group
1,4-phenylene group, naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, tetrahydronaphthalene-2,6-optionally substituted by one or two fluorine atoms Diyl group, 1,4-cyclohexenylene group which may be substituted by 1 to 2 fluorine atoms, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or Represents a pyridine-2,5-diyl group, but in each compound, transdecahydronaphthalene-trans-2,
6-diyl group, naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, tetrahydronaphthalene optionally substituted by one or two fluorine atoms
-2,6-diyl group, 1,4-cyclohexenylene group which may be substituted by a fluorine atom, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or The number of pyridine-2,5-diyl groups is preferably one or less, and the other rings are trans-1,4-cyclohexylene groups or 1-2.
It is preferably a 1,4-phenylene group which may be substituted by two fluorine atoms or a methyl group.

L^g, L^hAnd LⁱIs a linking group,
Independently a single bond, an ethylene group (-CH _TwoCH_Two-), 1,2-Propylene
Len group (-CH (CH_Three) CH_Two-And-CH_TwoCH (CH_Three)-), 1,4-butyl
Group, -COO-, -OCO-, -OCF_Two-, -CF_TwoO-, -CH = CH-, -CH = C
F-, -CF = CH-, -CF = CF-, -C≡C- or -CH = NN = CH-
Is a single bond, ethylene group, 1,4-butylene group, -COO-, -OC
O-, -OCF_Two-, -CF_TwoO-, -CF = CF-, -C≡C- or -CH = NN = CH
-Is preferable, and in (C2), at least one of them is (C2)
In 3), at least two of them may represent a single bond
preferable.

In (C2), the compound represented by formula (I) of the present invention
Are excluded.

More preferred forms of (C1) can be represented by the following general formulas (C1a) to (C1h).

[0278]

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In each of the above formulas, R ^f and R ^g are each independently a linear alkyl group having 1 to 7 carbon atoms, 2 to 7 carbon atoms.
A linear 1-alkenyl group, a linear 3-alkenyl group having 4 to 7 carbon atoms, a linear alkoxyl group having 1 to 3 carbon atoms or a terminal substituted by an alkoxyl group having 1 to 3 carbon atoms. Represents a linear alkyl group having 1 to 5 carbon atoms, 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 carbon Number of atoms
Represents 4 to 7 linear 3-alkenyl groups. However, ring G1 to ring
If G8 is an aromatic ring, the corresponding R ^f is except 1-alkenyl group and an alkoxyl group, when the ring H1~ ring H8 is an aromatic ring, the corresponding R ^g except 1-alkenyl groups and alkoxyl groups.

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

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

[0282]

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In the above formula, ring G1, ring G2, ring G3, ring H1, ring H2 and ring H3 have the above-mentioned meanings, ring I1 is ring G1, and ring I2 is ring
G2 and ring I3 each have the same meaning as ring G3. In each of the above compounds, transdecahydronaphthalene-
Trans-2,6-diyl group, naphthalene-2,6-diyl group optionally substituted by one or more fluorine atoms, tetrahydronaphthalene-2, optionally substituted by 1-2 fluorine atoms, 6-diyl group, 1,4-cyclohexenylene group which may be 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 may be substituted with a trans-1,4-cyclohexylene group or one or two fluorine atoms or methyl groups. , 4-phenylene group.

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

[0285]

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In the above formula, ring G1, ring G2, ring H1, ring H2, ring I1 and ring I2 have the above-mentioned meanings, and ring J1 is ring G1 and ring J2 is ring
Represents the same meaning as G2. In each of the above compounds, transdecahydronaphthalene-trans-2,6-diyl group, naphthalene-2,6-diyl group optionally substituted with one or more fluorine atoms, 1-2 fluorine atoms May be substituted with tetrahydronaphthalene-2,6
-Diyl group, 1,4 which may be substituted by a fluorine atom
-Cyclohexenylene group, 1,3-dioxane-trans-2,5
-Diyl group, pyrimidine-2,5-diyl group or pyridine-
The number of 2,5-diyl groups is preferably one or less, in which case the other ring may be substituted with a trans-1,4-cyclohexylene group or one or two fluorine atoms or methyl groups. 1,4-phenylene group.

[0287]

EXAMPLES Examples of the present invention are shown below to further explain the present invention. However, the present invention is not limited to these examples. Example 1 Synthesis of 2-ethoxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene (I-1)

[0288]

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(1-a) Synthesis of 6-hydroxy-transdecahydronaphthalen-2-one ethylene acetal 21 g of transdecahydronaphthalene-2,6-dione monoethylene acetal was dissolved in 100 mL of methanol and cooled to 10 ° C. or lower. While adding 4 g of sodium borohydride little by little, the mixture was stirred at room temperature for 1 hour. Water was added, the mixture was extracted with ethyl acetate, washed with water and saturated saline in this order, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 6-hydroxy-transdecahydronaphthalen-2-one ethylene acetal. 20 g of a yellow solid were obtained. (1-b) 6-ethoxy-transdecahydronaphthalene-2-
Synthesis of on-ethylene acetal 6-hydroxy-transdecahydronaphthalen-2-one obtained in (1-a) 20 g of ethylene acetal in N, N-dimethylformamide (DMF) 100 mL, 60% hydrogenation in DMF 30 mL While suspending 6 g of sodium, it was added dropwise while cooling to 10 ° C. or lower. After returning to room temperature and stirring for 30 minutes, a solution of 19 g of ethyl iodide in 50 mL of DMF was added dropwise while cooling to 10 ° C. or lower. 60 ℃
After heating and stirring for 8 hours, water and ethyl acetate were added, the organic layer was separated, washed with water and saturated saline, dried over anhydrous sodium sulfate, the solvent was distilled off, and silica gel column chromatography (hexane) was performed. And recrystallized from ethanol to obtain 14 g of 6-ethoxy-transdecahydronaphthalen-2-one ethylene acetal as a white solid. (1-c) 6-ethoxy-transdecahydronaphthalene-2-
Synthesis of ON 14 g of a white solid of 6-ethoxy-transdecahydronaphthalen-2-oneethyleneacetal obtained in (1-b) was dissolved in 70 mL of toluene, 40 mL of formic acid was added, and the mixture was stirred at room temperature for 1 hour. Water was added, the organic layer was separated, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order, dried over anhydrous sodium sulfate, and the solvent was distilled off to give 6-ethoxy-transdecahydronaphthalene-2. 10 g of a pale yellow solid were obtained. (1-d) 2-ethoxy-6- (3,4,5-trifluorophenyl)-
Synthesis of 1,2,3,4,7,8,9,10-transoctahydronaphthalene While 1.5 g of magnesium metal is suspended in 6 mL of tetrahydrofuran (THF), 3,4,5-trifluoro- A solution of 15 g of 1-bromobenzene in 70 mL of THF was added dropwise to prepare a Grignard reagent. While cooling the solution to 10 ° C. or lower, a solution of 10 g of 6-ethoxy-transdecahydronaphthalen-2-one obtained in (1-c) in 50 mL of THF was added dropwise, and the mixture was returned to room temperature and stirred for 1 hour. After adding 10% hydrochloric acid, the organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off. Dissolve the obtained oil in 80 mL of toluene,
2 g of p-toluenesulfonic acid monohydrate was added, and the mixture was heated and refluxed for 4 hours using a device equipped with a water separator until the distilled water disappeared. After cooling to room temperature, water was added, the organic layer was separated, washed with a saturated aqueous solution of sodium hydrogen carbonate, water and saturated saline in this order, dried over anhydrous magnesium sulfate, and the solvent was distilled off.
2-ethoxy-6- (3,4,5-trifluorophenyl) -1,2,3,4,
13 g of a pale yellow oil of 7,8,9,10-transoctahydronaphthalene was obtained. (1-e) Synthesis of 2-ethoxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene 2-ethoxy-6- (3,4,5- obtained in (1-d) Dissolve 13 g of (trifluorophenyl) -1,2,3,4,7,8,9,10-transoctahydronaphthalene in 70 mL of ethyl acetate, add 2 g of 5% palladium-carbon, and add hydrogen at room temperature for 6 hours. Hydrogenation was performed at a pressure of 490 KPa. The catalyst was filtered through celite, and the solvent was distilled off. The obtained oil was dissolved in 60 mL of DMF, and while cooling to 0 ° C., 3 g of potassium t-butoxide was added, followed by stirring for 2 hours. After adding water and hexane, the organic layer was separated, washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate, and the solvent was distilled off. Silica gel column chromatography (hexane)
And recrystallized from ethanol at -70 ° C or lower to obtain 4 g of 2-ethoxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene as a white solid.

The following compounds are obtained in the same manner.

2-methoxy-6- (4-fluorophenyl) transdecahydronaphthalene 2-ethoxy-6- (4-fluorophenyl) transdecahydronaphthalene 2-propyloxy-6- (4-fluorophenyl) transdeca Hydronaphthalene 2-butyloxy-6- (4-fluorophenyl) transdecahydronaphthalene 2-pentyloxy-6- (4-fluorophenyl) transdecahydronaphthalene 2-hexyloxy-6- (4-fluorophenyl) transdeca Hydronaphthalene 2- (2-propenyloxy) -6- (4-fluorophenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-fluorophenyl) transdecahydronaphthalene 2-methoxy-6 -(3,4-difluorophenyl) transdecahydronaphthalene 2-ethoxy-6- (3,4-difluorophenyl) transdecahydronaphthalene 2-propyl Xy-6- (3,4-difluorophenyl) transdecahydronaphthalene 2-butyloxy-6- (3,4-difluorophenyl) transdecahydronaphthalene 2-pentyloxy-6- (3,4-difluorophenyl) trans Decahydronaphthalene 2-hexyloxy-6- (3,4-difluorophenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3,4-difluorophenyl)
Transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3,4-difluorophenyl) transdecahydronaphthalene 2-methoxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene 2 -Propyloxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene 2-butyloxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene 2-pentyloxy-6- ( 3,4,5-trifluorophenyl) transdecahydronaphthalene 2-hexyloxy-6- (3,4,5-trifluorophenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3, 4,5-trifluorophenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3,4,5-trifluorophenyl) transdecahydronaphthalene

2-methoxy-6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-propyloxy-6- (4-tri (Fluoromethoxyphenyl) transdecahydronaphthalene 2-butyloxy-6- (4-trifluoromethoxyphenyl)
Transdecahydronaphthalene 2-pentyloxy-6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-hexyloxy-6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-methoxy-6- (3-fluoro- 4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (3-fluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-propyloxy-6- (3-fluoro-4-trifluoromethoxy Phenyl) transdecahydronaphthalene 2-butyloxy-6- (3-fluoro-4-trifluoromethoxyphenyl) transde Hydronaphthalene 2-pentyloxy-6- (3-fluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-hexyloxy-6- (3-fluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3-fluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3-fluoro-4-trifluoromethoxyphenyl) trans Decahydronaphthalene 2-methoxy-6- (3,5-difluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (3,5-difluoro-4-trifluoromethoxyphenyl) transdecahydro Naphthalene 2-propyloxy-6- (3,5-difluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-butyloxy-6- (3,5-difluoro -4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-pentyloxy-6- (3,5-difluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2-hexyloxy-6- (3,5-difluoro -4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3,5-difluoro-4-trifluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3,5-difluoro-4-
(Trifluoromethoxyphenyl) transdecahydronaphthalene

2-methoxy-6- (4-difluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (4-difluoromethoxyphenyl) transdecahydronaphthalene 2-propyloxy-6- (4-difluoromethoxyphenyl )
Transdecahydronaphthalene 2-butyloxy-6- (4-difluoromethoxyphenyl) transdecahydronaphthalene 2-pentyloxy-6- (4-difluoromethoxyphenyl)
Transdecahydronaphthalene 2-hexyloxy-6- (4-difluoromethoxyphenyl)
Transdecahydronaphthalene 2- (2-propenyloxy) -6- (4-difluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-difluoromethoxyphenyl) transdecahydronaphthalene 2 -Methoxy-6- (3-fluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (3-fluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-propyloxy-6- (3 -Fluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-butyloxy-6- (3-fluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-pentyloxy-6- (3-fluoro-4-difluoromethoxy Phenyl) transdecahydronaphthalene 2-hexyloxy-6- (3-fluoro-4-difluoromethoxyphenyl) tolan Decahydronaphthalene 2- (2-propenyloxy) -6- (3-fluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3-fluoro-4-difluoromethoxy Phenyl) transdecahydronaphthalene 2-methoxy-6- (3,5-difluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (3,5-difluoro-4-difluoromethoxyphenyl) transdeca Hydronaphthalene 2-propyloxy-6- (3,5-difluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-butyloxy-6- (3,5-difluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2 -Pentyloxy-6- (3,5-difluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2-hexyloxy-6- (3,5-difluoro-4- (Fluoromethoxyphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3,5-difluoro-4-difluoromethoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3 , 5-difluoro-4-
Difluoromethoxyphenyl) transdecahydronaphthalene

2-methoxy-6- (4-chlorophenyl) transdecahydronaphthalene 2-ethoxy-6- (4-chlorophenyl) transdecahydronaphthalene 2-propyloxy-6- (4-chlorophenyl) transdecahydronaphthalene 2 -Butyloxy-6- (4-chlorophenyl) transdecahydronaphthalene 2-pentyloxy-6- (4-chlorophenyl) transdecahydronaphthalene 2-hexyloxy-6- (4-chlorophenyl) transdecahydronaphthalene 2- (2 -Propenyloxy) -6- (4-chlorophenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-chlorophenyl)
Transdecahydronaphthalene 2-methoxy-6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2-ethoxy-6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2-propyloxy-6- ( 3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2-butyloxy-6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2-pentyloxy-6- (3-fluoro-4-chlorophenyl) transdecahydro Naphthalene 2-hexyloxy-6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2- (trans- 2-butenyloxy) -6- (3-fluoro-4-chlorophenyl) transdecahydronaphthalene 2-methoxy-6- (3,5-difluoro-4-chlorophenyl) transdeca Dronaphthalene 2-ethoxy-6- (3,5-difluoro-4-chlorophenyl) transdecahydronaphthalene 2-propyloxy-6- (3,5-difluoro-4-chlorophenyl) transdecahydronaphthalene 2-butyloxy-6 -(3,5-difluoro-4-chlorophenyl)
Transdecahydronaphthalene 2-pentyloxy-6- (3,5-difluoro-4-chlorophenyl) transdecahydronaphthalene 2-hexyloxy-6- (3,5-difluoro-4-chlorophenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (3,5-difluoro-4-chlorophenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3,5-difluoro-4-
Chlorophenyl) transdecahydronaphthalene

2-methoxy-6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2-ethoxy-6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2-propyloxy- 6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2-butyloxy-6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2-pentyloxy-6- (2,3, 4-trifluorophenyl) transdecahydronaphthalene 2-hexyloxy-6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (2,3,4- (Trifluorophenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (2,3,4-trifluorophenyl) transdecahydronaphthalene 2-methoxy-6- (2,3-difluoro-4- (Methylphenyl) transdecahydronaphthalene 2-ethoxy-6- ( 2,3-difluoro-4-methylphenyl) transdecahydronaphthalene 2-propyloxy-6- (2,3-difluoro-4-methylphenyl) transdecahydronaphthalene 2-butyloxy-6- (2,3-difluoro -4-methylphenyl)
Transdecahydronaphthalene 2-pentyloxy-6- (2,3-difluoro-4-methylphenyl) transdecahydronaphthalene 2-hexyloxy-6- (2,3-difluoro-4-methylphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (2,3-difluoro-4-methylphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (2,3-difluoro-4-
Methylphenyl) transdecahydronaphthalene 2-methoxy-6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2-ethoxy-6- (2,3-difluoro-4-methoxyphenyl) transdecahydro Naphthalene 2-propyloxy-6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2-butyloxy-6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2-pentyloxy -6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2-hexyloxy-6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2- (2-propenyloxy) -6- (2,3-difluoro-4-methoxyphenyl) transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (2,3-difluoro-4-
(Methoxyphenyl) transdecahydronaphthalene

2-methoxy-6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-ethoxy-6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-propyloxy-6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-butyloxy-6- [4- (trifluoromethyl) phenyl]
Transdecahydronaphthalene 2-pentyloxy-6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-hexyloxy-6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2- (2 -Propenyloxy) -6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- [4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-methoxy -6- [3-Fluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-ethoxy-6- [3-fluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-propyloxy- 6- [3-Fluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-butyloxy-6- [3-fluoro-4- (trifluoromethyl) phenyl] transdecahydride Naphthalene 2-pentyloxy-6- [3-fluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-hexyloxy-6- [3-fluoro-4- (trifluoromethyl) phenyl] transdecahydro Naphthalene 2- (2-propenyloxy) -6- [3-fluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- [3-fluoro-4- ( Trifluoromethyl) phenyl] transdecahydronaphthalene 2-methoxy-6- [3,5-difluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-ethoxy-6- [3,5-difluoro-4 -(Trifluoromethyl) phenyl] transdecahydronaphthalene 2-propyloxy-6- [3,5-difluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-butyloxy-6- [3,5- Difluoro-4- (trif Oromethyl) phenyl] transdecahydronaphthalene 2-pentyloxy-6- [3,5-difluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2-hexyloxy-6- [3,5-difluoro-4 -(Trifluoromethyl) phenyl] transdecahydronaphthalene 2- (2-propenyloxy) -6- [3,5-difluoro-4- (trifluoromethyl) phenyl] transdecahydronaphthalene 2- (trans-2- (Butenyloxy) -6- [3,5-difluoro-4-
(Trifluoromethyl) phenyl] transdecahydronaphthalene

2-methoxy-6- [4- (3-butenylphenyl)]
Transdecahydronaphthalene 2-ethoxy-6- [4- (3-butenylphenyl)] transdecahydronaphthalene 2-propyloxy-6- [4- (3-butenylphenyl)] transdecahydronaphthalene 2-butyloxy -6- [4- (3-butenylphenyl)] transdecahydronaphthalene 2-pentyloxy-6- [4- (3-butenylphenyl)] transdecahydronaphthalene 2-hexyloxy-6- [4- (3-Butenylphenyl)] transdecahydronaphthalene 2- (2-propenyloxy) -6- [4- (3-butenylphenyl)]
Transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- [4- (3-butenylphenyl)] transdecahydronaphthalenethalene 2-methoxy-6- [4- (trans-3-pentenylphenyl)] Transdecahydronaphthalene 2-ethoxy-6- [4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2-propyloxy-6- [4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2 -Butyloxy-6- [4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2-pentyloxy-6- [4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2-hexyloxy-6 -[4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2- (2-propenyloxy) -6- [4- (trans-3-pentenylphenyl)] transdecahydronaphthalene 2- (trans-2 -Bute Yloxy) -6- [4- (trans-3-pentenyl phenyl) trans-decahydronaphthalene

Example 2 Synthesis of 2- (trans-2-butenyloxy) -6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene (I-2)

[0299]

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(2-a) 6- (3,5-difluorophenyl) -1,2,
Synthesis of 3,4,7,8,9,10-transoctahydronaphthalen-2-one ethylene acetal Similarly to (1-d), transdecahydronaphthalene-2,6-dione monoethylene acetal 32 g was 3,3 6- (3,5-difluorophenyl) -1,2,3,4,7,8,9 by reacting with a Grignard reagent prepared from 5-difluoro-1-bromobenzene, dehydrating and reacetalizing 40 g of a pale yellow liquid of 10,10-transoctahydronaphthalen-2-one ethylene acetal was obtained. (2-b) Synthesis of 6- (3,5-difluorophenyl) -transdecahydronaphthalen-2-one ethylene acetal 6- (3,5-difluorophenyl) -1, obtained in (2-a) 2,3,4,
7,8,9,10-Transoctahydronaphthalen-2-one 40 g of ethylene acetal was subjected to catalytic hydrogen reduction in the same manner as (1-e) to give 6- (3,5-difluorophenyl) -transdecahydronaphthalene 39 g of a pale yellow oil of 2-one ethylene acetal was obtained. (2-c) Synthesis of 6- (3,5-difluorophenyl) -transdecahydronaphthalen-2-one 6- (3,5-difluorophenyl) -transdecahydronaphthalene obtained in (2-b) 39 g of 2-one ethylene acetal
By deacetalization in the same manner as (1-c), 6- (3,5-
Difluorophenyl) -transdecahydronaphthalene-2
29 g of a pale yellow oil were obtained. Synthesis of (2-d) 6- (3,5-difluorophenyl) -transdecahydronaphthalen-2-ol 6- (3,5-difluorophenyl) -transdecahydronaphthalene obtained in (2-c) 29 g of 2-one was reduced in the same manner as (1-a) to obtain 23 g of a pale yellow oily substance of 6- (3,5-difluorophenyl) -transdecahydronaphthalen-2-ol. Synthesis of (2-e) 2- (trans-2-butenyloxy) -6- (3,5-difluorophenyl) -transdecahydronaphthalene 6- (3,5-difluorophenyl obtained in (2-d) ) -Transdecahydronaphthalen-2-ol 23 g was etherified in the same manner as 1-chloro-trans-2-butene and (1-b) to give 2- (trans-2-butenyloxy) -6- ( 19 g of a pale yellow oil of 3,5-difluorophenyl) -transdecahydronaphthalene was obtained. (2-f) 2- (trans-2-butenyloxy) -6- (4-cyano-
Synthesis of 3,5-difluorophenyl) -transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (3,
5-difluorophenyl) -transdecahydronaphthalene
While cooling 19 g of an 80 mL THF solution to -70 ° C, 40 mL of a 1.6 M butyllithium-hexane solution was added dropwise over 10 minutes while maintaining the internal temperature at -50 ° C or lower. 30 while cooling to -70 ° C
After stirring for minutes, carbon dioxide was blown in while maintaining the internal temperature at -50 ° C or lower. After the exotherm subsided, the temperature was raised to room temperature, water and ethyl acetate were added, the organic layer was separated, the organic layer was washed with water and saturated brine in that order, dried over anhydrous sodium sulfate, and the solvent was distilled off. . The obtained yellow solid was dissolved in 1,2-dichloroethane (200 mL), thionyl chloride (14 g), pyridine
0.1 mL and DMF10mL were added, and it stirred at room temperature for 6 hours. After the solvent was distilled off, 100 mL of dichloromethane was added, and ammonia gas was blown while cooling to 0 ° C. After the exotherm subsided, the mixture was stirred at room temperature for 2 hours, and the precipitated crystals were filtered. The obtained yellow crystals were dissolved in 100 mL of DMF, and 10 g of oxalyl chloride was added dropwise while cooling to 0 ° C. After stirring at room temperature for 1 hour, the mixture was poured into ice water and extracted with toluene. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate, water and saturated saline in this order, and dried over anhydrous sodium sulfate. The solvent is distilled off, and silica gel column chromatography- (toluene)
And recrystallized from ethanol to give 2- (trans-2-
5 g of white crystals of butenyloxy) -6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene were obtained.

The following compounds are obtained in the same manner.

2-methoxy-6- (4-cyanophenyl) -transdecahydronaphthalene 2-ethoxy-6- (4-cyanophenyl) -transdecahydronaphthalene 2-propyloxy-6- (4-cyanophenyl) -Transdecahydronaphthalene 2-butyloxy-6- (4-cyanophenyl) -transdecahydronaphthalene 2-pentyloxy-6- (4-cyanophenyl) -transdecahydronaphthalene 2-hexyloxy-6- (4- (Cyanophenyl) -transdecahydronaphthalene 2- (2-propenyloxy) -6- (4-cyanophenyl) -transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-cyanophenyl)
-Transdecahydronaphthalene 2-methoxy-6- (4-cyano-3-fluorophenyl) -transdecahydronaphthalene 2-ethoxy-6- (4-cyano-3-fluorophenyl) -transdecahydronaphthalene 2-propyl Oxy-6- (4-cyano-3-fluorophenyl)-
Transdecahydronaphthalene 2-butyloxy-6- (4-cyano-3-fluorophenyl) -transdecahydronaphthalene 2-pentyloxy-6- (4-cyano-3-fluorophenyl)-
Transdecahydronaphthalene 2-hexyloxy-6- (4-cyano-3-fluorophenyl)-
Transdecahydronaphthalene 2- (2-propenyloxy) -6- (4-cyano-3-fluorophenyl) -transdecahydronaphthalene 2- (trans-2-butenyloxy) -6- (4-cyano-3-fluoro (Phenyl) -transdecahydronaphthalene 2-methoxy-6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene 2-ethoxy-6- (4-cyano-3,5-difluorophenyl) -trans Decahydronaphthalene 2-propyloxy-6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene 2-butyloxy-6- (4-cyano-3,5-difluorophenyl)
-Transdecahydronaphthalene 2-pentyloxy-6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene 2-hexyloxy-6- (4-cyano-3,5-difluorophenyl) -trans Decahydronaphthalene 2- (2-propenyloxy) -6- (4-cyano-3,5-difluorophenyl) -transdecahydronaphthalene

Methyl 4- (6-methoxy-transdecahydronaphthalen-2-yl) benzoate 4- (6-ethoxy-transdecahydronaphthalen-2-yl)
Methyl benzoate 4- (6-propyloxy-transdecahydronaphthalene-2
-Yl) methyl benzoate 4- (6-butyloxy-transdecahydronaphthalene-2-
Yl) Methyl benzoate 4- (6-pentyloxy-transdecahydronaphthalene-2
-Yl) methyl benzoate 4- (6-hexyloxy-transdecahydronaphthalene-2
-Yl) Methyl benzoate 4- [6- (2-pentenyloxy) -transdecahydronaphthalen-2-yl] methyl benzoate 4- [6- (trans-2-butenyloxy) -transdecahydronaphthalene-2- Yl] methyl benzoate 3-fluoro-4- (6-methoxy-transdecahydronaphthalen-2-yl) methyl benzoate 3-fluoro-4- (6-ethoxy-transdecahydronaphthalen-2-yl) benzoic acid Methyl 3-fluoro-4- (6-propyloxy-transdecahydronaphthalen-2-yl) benzoate Methyl 3-fluoro-4- (6-butyloxy-transdecahydronaphthalen-2-yl) benzoate 3- Methyl fluoro-4- (6-pentyloxy-transdecahydronaphthalen-2-yl) benzoate Methyl 3-fluoro-4- (6-hexyloxy-transdecahydronaphthalen-2-yl) benzoate 3-fluoro- 4- [6- (2-pentenyloxy) -transdeca Methyl dronaphthalen-2-yl] benzoate Methyl 3-fluoro-4- [6- (trans-2-butenyloxy) -transdecahydronaphthalen-2-yl] benzoate 3,5-difluoro-4- (6- Methyl methoxy-transdecahydronaphthalen-2-yl) benzoate Methyl 3,5-difluoro-4- (6-ethoxy-transdecahydronaphthalen-2-yl) benzoate 3,5-difluoro-4- (6- Methyl propyloxy-transdecahydronaphthalen-2-yl) benzoate 3,5-difluoro-4- (6-butyloxy-transdecahydronaphthalen-2-yl) methyl 3,5-difluoro-4- (6 Methyl 3,5-difluoro-4- (6-hexyloxy-transdecahydronaphthalen-2-yl) benzoate 3,5-difluoro-4-methyl-pentyloxy-transdecahydronaphthalen-2-yl) benzoate [6- (2-pentenyloxy) -transdecahydronaphthalen-2-yl] Ikikosan methyl 3,5-difluoro-4- [6- (trans-2-butenyloxy) - trans-decahydronaphthalene-2-yl] benzoate

Example 3 2- [6- (3-butenyl) naphthalene
-2-yl] -6-propyl-transdecahydronaphthalene (I
Synthesis of -3)

[0305]

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(3-a) 2- (6-methoxynaphthalen-2-yl)
Synthesis of -trans-6-propyl-3,4,4a, 5,6,7,8,8a-transoctahydronaphthalene As in (1-d), 24 g of 6-propyldecahydronaphthalen-2-one was React with a Grignard reagent prepared from 6-methoxy-2-bromonaphthalene and dehydrate to give 2- (6
-Methoxynaphthalen-2-yl) -trans-6-propyl-3,
32 g of a pale yellow liquid of 4,4a, 5,6,7,8,8a-transoctahydronaphthalene was obtained. (3-b) 2- (6-methoxynaphthalen-2-yl) -trans-6-
Synthesis of propyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -trans-6-propyl-3,4,4a, 5,6,7,8, obtained in (3-a) 8a-trans octahydronaphthalene 32g was catalytically reduced in the same manner as (1-e),
By isomerization, 30 g of a pale yellow oil of 2- (6-methoxynaphthalen-2-yl) -trans-6-propyl-transdecahydronaphthalene was obtained. (3-c) Synthesis of 6- (trans-6-propyl-3,4,4a, 5,6,7,8,8a-transoctahydronaphthalen-2-yl) -2-naphthol (3-b) 2- (6-methoxynaphthalen-2-yl) -trans-6-propyl-transdecahydronaphthalene obtained in 30 g
Was dissolved in 150 mL of glacial acetic acid and 150 mL of a 48% aqueous solution of hydrobromic acid, and 8
Heated to reflux for an hour. After cooling to room temperature, water and ethyl acetate were added, and the organic layer was separated. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated saline in this order, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 24 g of 6- (trans-6-propyl-3,4,4a, 5,6,7,8,8a-transoctahydronaphthalen-2-yl) -2-naphthol as yellow crystals. Was. (3-d) Synthesis of 2- (6-trifluoromethanesulfonyloxynaphthalen-2-yl) -trans-6-propyl-transdecahydronaphthalene 6- (trans-6-propyl) obtained in (3-c) -3,4,4a, 5,6,
A solution of 7,8,8a-transoctahydronaphthalen-2-yl) -2-naphthol in 24 g of yellow crystals in 100 mL of dichloromethane was added to
While cooling to ° C., a solution of 25 g of trifluoromethanesulfonic anhydride in 120 mL of dichloromethane was added dropwise, followed by a solution of 14 g of pyridine in 70 mL of dichloromethane. After stirring at room temperature for 1 hour, 10% hydrochloric acid was added, and the organic layer was separated.
The extract was washed with water, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated saline in this order, and dried over anhydrous sodium sulfate. After evaporating the solvent, silica gel column chromatography (hexane)
Then, 25 g of a white solid of 2- (6-trifluoromethanesulfonyloxynaphthalen-2-yl) -trans-6-propyl-transdecahydronaphthalene was obtained. Synthesis of (3-e) 2- [6- (3-butenyl) naphthalen-2-yl] -6-propyl-transdecahydronaphthalene 2- (obtained in (3-d) cooled to 10 ° C. or lower 6-trifluoromethanesulfonyloxynaphthalen-2-yl) -trans-
6-propyl-transdecahydronaphthalene 25 g, dichlorobis (diphenylphosphinoethane) nickel (II) 0.8 g
1.5 g of metallic magnesium and 4-bromo-1 in a 130 mL solution of THF
-Drop the Grignard reagent prepared from 9 g of butene,
The mixture was returned to room temperature and stirred for 6 hours. After adding 10% hydrochloric acid, the organic layer was separated, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane).
Recrystallization from toluene gave 3 g of 2- [6- (3-butenyl) naphthalen-2-yl] -6-propyl-transdecahydronaphthalene as white crystals.

The following compounds are obtained in the same manner.

2- [6- (3-butenyl) naphthalen-2-yl] -6-
Methyl-transdecahydronaphthalene 2- [6- (3-butenyl) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [6- (3-butenyl) naphthalen-2-yl] -6- Butyl-transdecahydronaphthalene 2- [6- (3-butenyl) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [6- (3-butenyl) naphthalen-2-yl] -6- Hexyl-transdecahydronaphthalene 2- [6- (3-butenyl) naphthalen-2-yl] -6-heptyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl]- 6-
Methyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Ethyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Propyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Butyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Pentyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Hexyl-transdecahydronaphthalene 2- [6- (trans-3-pentenyl) naphthalen-2-yl] -6-
Heptyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-methyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-ethyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-propyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-butyl-transdecahydronaphthalene 2- (6-methoxynaphthalene-2- Yl) -6-pentyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-hexyl-transdecahydronaphthalene 2- (6-methoxynaphthalen-2-yl) -6-heptyl-trans Decahydronaphthalene 2- [6- (2-propenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [6- (2-propenyloxy) naphthalen-2-yl] -6-ethyl -Transdecahydronaphthalene 2- [6- (2-propane 2-oxy) naphthalen-2-yl] -6-propyl-transdecahydronaphthalene 2- [6- (2-propenyloxy) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2- [6- (2 -Propenyloxy) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [6- (2-propenyloxy) naphthalen-2-yl] -6-hexyl-transdecahydronaphthalene 2- [6- (2-propenyloxy) naphthalen-2-yl] -6-heptyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-Methyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-Ethyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-Propyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-butyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-pentyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-hexyl-transdecahydronaphthalene 2- [6- (trans-2-butenyloxy) naphthalen-2-yl]
-6-heptyl-transdecahydronaphthalene

2- [1-Fluoro-2- (3-butenyl) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Propyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Butyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-heptyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-methyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-ethyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-propyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-butyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-pentyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-hexyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (2- (Propenyloxy) naphthalene-6-
Yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2 -(Trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-propyl- Transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) ) Naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahydronaphthalene 2- [ 1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-he Chill - trans-decahydronaphthalene

2- [3-fluoro-2- (3-butenyl) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Propyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Butyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-propyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-heptyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-methyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-ethyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-propyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-butyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-pentyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-hexyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (2- (Propenyloxy) naphthalene-6-
Yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-propyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2 -(Trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-propyl- Transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) ) Naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahydronaphthalene 2- [ 3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-he Chill - trans-decahydronaphthalene

2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) Naphthalene-6-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-butyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-hexyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,3-difluoro -2- (trans-3-pentenyl) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl]- 6-propyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,3-difluoro- 2- (trans-3-pentenyl) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,3-difluoro-2-methoxynaphthalen-6-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-propyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-hexyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-heptyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,3-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-2-butenyloxy) naphthalene- 6-yl] -6-propyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 3-Difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-2-butenyloxy) naphthalene-6 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,3-difluoro-2- (trans-2-butenylo) Shi) naphthalene-6-yl] -6-heptyl - trans-decahydronaphthalene

2- [1-Fluoro-3- (3-butenyl) naphthalene
-7-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Propyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Butyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Hexyl-transdecahydronaphthalene 2- [1-fluoro-3- (3-butenyl) naphthalen-7-yl] -6-
Heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-3-pentenyl) naphthalene-
7-yl] -6-heptyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-methyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalene- 7-yl) -6-ethyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-propyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalene- 7-yl) -6-butyl-transdecahydronaphthalene 2- (1-fluoro-
3-methoxynaphthalen-7-yl) -6-pentyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-hexyl-transdecahydronaphthalene 2- (1-fluoro- 3-methoxynaphthalen-7-yl) -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3 -(Trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-propyl- Transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) ) Naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-hexyl-transdecahydronaphthalene 2- [ 1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-he Chill - trans-decahydronaphthalene

2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) Naphthalene-7-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-butyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro -3- (trans-3-pentenyl) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl]- 6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,2-difluoro- 3- (trans-3-pentenyl) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalene- 7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 2-Difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalene-7 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenylo) Shi) naphthalene-7-yl] -6-heptyl - trans-decahydronaphthalene

2- [1-Fluoro-7- (3-butenyl) naphthalene
-3-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Ethyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Propyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Butyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Pentyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Hexyl-transdecahydronaphthalene 2- [1-fluoro-7- (3-butenyl) naphthalen-3-yl] -6-
Heptyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-7- (trans-3-pentenyl) naphthalene-
3-yl] -6-heptyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-methyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalene- 7-yl) -6-ethyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-propyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalene- 7-yl) -6-butyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-pentyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalene- 7-yl) -6-hexyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (2- (Propenyloxy) naphthalene-7-
Yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3 -(Trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-propyl- Transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) ) Naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-hexyl-transdecahydronaphthalene 2- [ 1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-he Tyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-methyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6- Ethyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-propyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6- Butyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-pentyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6- Hexyl-transdecahydronaphthalene 2- (1-fluoro-3-methoxynaphthalen-7-yl) -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-3- (2-propenyloxy) naphthalene-7-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-3 -(Trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-propyl- Transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) ) Naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-hexyl-transdecahydronaphthalene 2- [ 1-fluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-he Chill - trans-decahydronaphthalene

2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) Naphthalen-2-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-butyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-hexyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-Heptyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro -6- (trans-3-pentenyl) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl]- 6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2- [1,8-difluoro- 6- (trans-3-pentenyl) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,8-difluoro-6-methoxynaphthalen-2-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,8
-Difluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
2-yl] -6-butyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-hexyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-heptyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,8-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-2-butenyloxy) naphthalene- 2- [yl] -6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 8-Difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-2-butenyloxy) naphthalene-2 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,8-difluoro-6- (trans-2-butenylo Shi) naphthalen-2-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) Naphthalene-7-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-butyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Pentyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-hexyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,6-difluoro -3- (trans-3-pentenyl) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl]- 6-propyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,6-difluoro- 3- (trans-3-pentenyl) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,6-difluoro-3-methoxynaphthalen-7-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-propyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-hexyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-heptyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,6-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-2-butenyloxy) naphthalene- 7-yl] -6-propyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 6-Difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-2-butenyloxy) naphthalene-7 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,6-difluoro-3- (trans-2-butenylo) Shi) naphthalene-7-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,3,8-trifluoro-6- (3-butenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6 -(3-butenyl) naphthalene-2-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (3-butenyl) naphthalene-2-
Yl] -6-propyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (3-butenyl) naphthalene-2-
Yl] -6-butyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (3-butenyl) naphthalene-2-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (3-butenyl) naphthalene-2-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (3-butenyl) naphthalene-2-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,3,8-trifluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans- 3-pentenyl) naphthalen-2-yl] -6-propyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-butyl -Transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3,8- Trifluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-hexyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-3-pentenyl) na The array type 2-yl] -6-heptyl - trans decahydronaphthalene 2- (1,3,8-trifluoro-6-methoxy-2-yl)
-6-Methyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-Ethyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-Propyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-butyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-pentyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-hexyl-transdecahydronaphthalene 2- (1,3,8-trifluoro-6-methoxynaphthalen-2-yl)
-6-heptyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,3 , 8-Trifluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (2-propenyloxy) naphthalene 2-yl] -6-propyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2 -[1,3,8-trifluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (2 -Propenyloxy) naphthalen-2-yl] -6-hexyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (2-propenyloxy) naphthalen-2-yl] -6-heptyl -Transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,3,8- Trifluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-2-butenyloxy) naphthalene- 2-yl] -6-propyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2 -[1,3,8-trifluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- ( Trans-2-butenyloxy) naphthalen-2-yl] -6-hexyl-transdecahydronaphthalene 2- [1,3,8-trifluoro-6- (trans-2-bute Yloxy) naphthalen-2-yl] -6-heptyl - trans-decahydronaphthalene

2- [3-fluoro-2- (3-butenyl) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Propyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Butyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-propyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-heptyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-methyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-ethyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-propyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-butyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-pentyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalene- 6-yl) -6-hexyl-transdecahydronaphthalene 2- (3-fluoro-2-methoxynaphthalen-6-yl) -6-heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (2- (Propenyloxy) naphthalene-6-
Yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-propyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-hexyl-transdecahydronaphthalene 2- [3-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-heptyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [3-fluoro-2 -(Trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-propyl- Transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) ) Naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahydronaphthalene 2- [ 3-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-he Chill - trans-decahydronaphthalene

2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) Naphthalen-2-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-Butyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-hexyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (3-butenyl) naphthalen-2-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro -6- (trans-3-pentenyl) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl]- 6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2- [1,7-difluoro- 6- (trans-3-pentenyl) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-3-pentenyl) naphthalen-2-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,7-difluoro-6-methoxynaphthalen-2-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-butyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-hexyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (2-propenyloxy) naphthalene
-2-yl] -6-heptyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,7-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-ethyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-2-butenyloxy) naphthalene- 2- [yl] -6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 7-Difluoro-6- (trans-2-butenyloxy) naphthalen-2-yl] -6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-2-butenyloxy) naphthalene-2 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,7-difluoro-6- (trans-2-butenylo Shi) naphthalen-2-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) Naphthalene-7-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-butyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-Hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (3-butenyl) naphthalen-7-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro -3- (trans-3-pentenyl) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl]- 6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,2-difluoro- 3- (trans-3-pentenyl) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,2-difluoro-3-methoxynaphthalen-7-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-butyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (2-propenyloxy) naphthalene
-7-yl] -6-heptyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalene- 7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 2-Difluoro-3- (trans-2-butenyloxy) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenyloxy) naphthalene-7 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,2-difluoro-3- (trans-2-butenylo) Shi) naphthalene-7-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,2,8-trifluoro-3- (3-butenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3 -(3-Butenyl) naphthalene-7-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (3-butenyl) naphthalene-7-
Yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (3-butenyl) naphthalene-7-
Yl] -6-butyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (3-butenyl) naphthalene-7-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (3-butenyl) naphthalene-7-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (3-butenyl) naphthalene-7-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,2,8-trifluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans- 3-pentenyl) naphthalen-7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-butyl -Transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8- Trifluoro-3- (trans-3-pentenyl) naphthalen-7-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-3-pentenyl) na The array type-7-yl] -6-heptyl - trans decahydronaphthalene 2- (1,2,8- trifluoro-3-methoxynaphthalene-7-yl)
-6-Methyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-Ethyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-Propyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-butyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-pentyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-hexyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-3-methoxynaphthalen-7-yl)
-6-heptyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (2-propenyloxy) naphthalen-7-yl] -6-methyl-transdecahydronaphthalene 2- [1,2 , 8-Trifluoro-3- (2-propenyloxy) naphthalen-7-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (2-propenyloxy) naphthalene -7-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (2-propenyloxy) naphthalen-7-yl] -6-butyl-transdecahydronaphthalene 2 -[1,2,8-trifluoro-3- (2-propenyloxy) naphthalen-7-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (2 -Propenyloxy) naphthalen-7-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (2-propenyloxy) naphthalen-7-yl] -6-heptyl -Transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,2,8- Trifluoro-3- (trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-2-butenyloxy) naphthalene- 6-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2 -[1,2,8-trifluoro-3- (trans-2-butenyloxy) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- ( Trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-3- (trans-2-bute Yloxy) naphthalen-6-yl] -6-heptyl - trans-decahydronaphthalene

2- [1-Fluoro-2- (3-butenyl) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Propyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Butyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (3-butenyl) naphthalen-6-yl] -6-
Heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-3-pentenyl) naphthalene-
6-yl] -6-heptyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-methyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-ethyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-propyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-butyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-pentyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalene- 6-yl) -6-hexyl-transdecahydronaphthalene 2- (1-fluoro-2-methoxynaphthalen-6-yl) -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (2- (Propenyloxy) naphthalene-6-
Yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-propyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1-fluoro-2- (2-propenyloxy) naphthalene-6-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1-fluoro-2 -(Trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-propyl- Transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) ) Naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahydronaphthalene 2- [ 1-fluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-he Chill - trans-decahydronaphthalene

2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) Naphthalene-6-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-butyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-Hexyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro -2- (trans-3-pentenyl) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl]- 6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,7-difluoro- 2- (trans-3-pentenyl) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,7-difluoro-2-methoxynaphthalen-6-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-hexyl-transdecahydronaphthalene 2
-[1,7-difluoro-2- (2-propenyloxy) naphthalen-6-yl] -6-heptyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-2-butenyloxy) naphthalene -6-yl] -6-methyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [ 1,7-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-propyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-2-butenyloxy) naphthalene- 6-yl] -6-butyl-transdecahydronaphthalene 2- [1,7-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1 , 7-Difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-hexyl-transdecahi B naphthalene 2- [1,7-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) Naphthalene-6-yl]
-6-Ethyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-Propyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-butyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-Hexyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (3-butenyl) naphthalen-6-yl]
-6-heptyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro 2- (trans-3-pentenyl) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl]- 6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,8-difluoro- 2- (trans-3-pentenyl) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6 -Hexyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-3-pentenyl) naphthalen-6-yl] -6-heptyl-tra Nsdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Methyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Ethyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Propyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Butyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Pentyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Hexyl-transdecahydronaphthalene 2- (1,8-difluoro-2-methoxynaphthalen-6-yl) -6-
Heptyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-methyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-butyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-hexyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (2-propenyloxy) naphthalene
-6-yl] -6-heptyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,8-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-ethyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-2-butenyloxy) naphthalene- 6-yl] -6-propyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-butyl-transdecahydronaphthalene 2- [1 , 8-Difluoro-2- (trans-2-butenyloxy) naphthalen-6-yl] -6-pentyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-2-butenyloxy) naphthalene-6 -Yl] -6-hexyl-transdecahydronaphthalene 2- [1,8-difluoro-2- (trans-2-butenylo) Shi) naphthalene-6-yl] -6-heptyl - trans-decahydronaphthalene

2- [1,2,8-trifluoro-7- (3-butenyl) naphthalen-3-yl] -6-methyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7 -(3-butenyl) naphthalene-3-
Yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (3-butenyl) naphthalene-3-
Yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (3-butenyl) naphthalene-3-
Yl] -6-butyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (3-butenyl) naphthalene-3-
Yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (3-butenyl) naphthalene-3-
Yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (3-butenyl) naphthalene-3-
Yl] -6-heptyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-3-pentenyl) naphthalen-3-yl] -6-methyl-transdecahydronaphthalene 2- [ 1,2,8-trifluoro-7- (trans-3-pentenyl) naphthalen-3-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans- 3-pentenyl) naphthalen-3-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-3-pentenyl) naphthalen-3-yl] -6-butyl -Transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-3-pentenyl) naphthalen-3-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8- Trifluoro-7- (trans-3-pentenyl) naphthalen-3-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-3-pentenyl) na The array type 3-yl] -6-heptyl - trans decahydronaphthalene 2- (1,2,8- trifluoro-7-methoxynaphthalene-3-yl)
-6-methyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-Ethyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-Propyl-transdecahydronaphthalen 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-butyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-pentyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-hexyl-transdecahydronaphthalene 2- (1,2,8-trifluoro-7-methoxynaphthalen-3-yl)
-6-heptyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (2-propenyloxy) naphthalen-3-yl] -6-methyl-transdecahydronaphthalene 2- [1,2 , 8-Trifluoro-7- (2-propenyloxy) naphthalen-3-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (2-propenyloxy) naphthalene -3-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (2-propenyloxy) naphthalen-3-yl] -6-butyl-transdecahydronaphthalene 2 -[1,2,8-trifluoro-7- (2-propenyloxy) naphthalen-3-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (2 -Propenyloxy) naphthalen-3-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (2-propenyloxy) naphthalen-3-yl] -6-heptyl -Transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-2-butenyloxy) naphthalen-3-yl] -6-methyl-transdecahydronaphthalene 2- [1,2,8- Trifluoro-7- (trans-2-butenyloxy) naphthalen-3-yl] -6-ethyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-2-butenyloxy) naphthalene- 3-yl] -6-propyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-2-butenyloxy) naphthalen-3-yl] -6-butyl-transdecahydronaphthalene 2 -[1,2,8-trifluoro-7- (trans-2-butenyloxy) naphthalen-3-yl] -6-pentyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- ( Trans-2-butenyloxy) naphthalen-3-yl] -6-hexyl-transdecahydronaphthalene 2- [1,2,8-trifluoro-7- (trans-2-bute Yloxy) naphthalen-3-yl] -6-heptyl - trans-decahydronaphthalene

Example 4 6- (1,2-Difluoronaphthalene)
-6-yl) -2-propyl-transdecahydronaphthalene (I
Synthesis of -4)

[0327]

Embedded image

(4-a) 6- (1,2-difluoronaphthalene-6-
Synthesis of yl) -2-propyl-1,2,3,4,7,8,9,10-transoctahydronaphthalene In the same manner as in (1-d), 12 g of 6-propyldecahydronaphthalen-2-one was obtained. By reacting with a Grignard reagent prepared from 1,2-difluoro-6-bromonaphthalene and dehydrating
6- (1,2-difluoronaphthalen-6-yl) -2-propyl-1,
15 g of a pale yellow liquid of 2,3,4,7,8,9,10-transoctahydronaphthalene was obtained. (4-b) Synthesis of 6- (1,2-difluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (1,2-difluoronaphthalene-6 obtained in (4-a) -Il)
By catalytic hydrogen reduction of 15 g of -2-propyl-1,2,3,4,7,8,9,10-transoctahydronaphthalene in the same manner as (1-e) and isomerization, 6- (1 Thus, 3 g of a white solid of 2,2-difluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene was obtained.

The following compounds are obtained in the same manner.

6- (2-fluoronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-fluoronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2- Fluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-fluoronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-fluoronaphthalen-6-yl)- 2-pentyl-transdecahydronaphthalene 6- (2-fluoronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-fluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1,2-difluoronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (1,2-difluoronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1 , 2-Difluoronaphthalen-6-yl) -2-butyl-transdeca Hydronaphthalene 6- (1,2-difluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,2-difluoronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,2-difluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2,3-difluoronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2,3 -Difluoronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2,3-difluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2,3-difluoronaphthalene- 6-yl) -2-butyl-transdecahydronaphthalene 6- (2,3-difluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2,3-difluoronaphthalen-6-yl) 2-hexyl-transdecahydronaphthalene 6- (2,3-difluoronaph Ren-6-yl) -2-heptyl - trans decahydronaphthalene 6- (1,2,3-trifluoro-6-yl) -2-methyl -
Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-propyl
-Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-pentyl
-Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-hexyl
-Transdecahydronaphthalene 6- (1,2,3-trifluoronaphthalen-6-yl) -2-heptyl
-Transdecahydronaphthalene 6- (1,7-difluoronaphthalen-3-yl) -2-methyl-transdecahydronaphthalene 6- (1,7-difluoronaphthalen-3-yl) -2-ethyl-transdecahydro Naphthalene 6- (1,7-difluoronaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1,7-difluoronaphthalen-3-yl) -2-butyl-transdecahydronaphthalene 6- ( 1,7-difluoronaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1,7-difluoronaphthalen-3-yl) -2-hexyl-transdecahydronaphthalene 6- (1,7- Difluoronaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-methyl-
Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-propyl
-Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-pentyl
-Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-hexyl
-Transdecahydronaphthalene 6- (1,2,8-trifluoronaphthalen-6-yl) -2-heptyl
-Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-methyl-
Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-propyl
-Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-pentyl
-Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-hexyl
-Transdecahydronaphthalene 6- (1,6,7-trifluoronaphthalen-6-yl) -2-heptyl
-Transdecahydronaphthalene 6- (1,2,3,8-tetrafluoronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (1,2,3,8-tetrafluoronaphthalene-6- Yl) -2-ethyl-transdecahydronaphthalene 6- (1,2,3,8-tetrafluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (1,2,3,8- Tetrafluoronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,2,3,8-tetrafluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1, 2,3,8-tetrafluoronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,2,3,8-tetrafluoronaphthalen-6-yl) -2-heptyl-transdecahydro Naphthalene

6- (2-trifluoromethoxynaphthalene-6-
Yl) -2-methyl-transdecahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2 -Propyl-transdecahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2-pentyl-trans Decahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-trifluoromethoxynaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6 -(1-Fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-methyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-ethyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-butyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-hexyl-transdecahydronaphthalene 6- (1-fluoro-2-trifluoromethoxynaphthalene-6-
Yl) -2-heptyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-methyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-ethyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-propyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-butyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-pentyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-hexyl-transdecahydronaphthalene 6- (2-trifluoromethoxy-3-fluoronaphthalene-6-
Yl) -2-heptyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-methyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-propyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,3-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-methyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-ethyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-butyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-hexyl-transdecahydronaphthalene 6- (1-fluoro-7-trifluoromethoxynaphthalene-3-
Yl) -2-heptyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-methyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-propyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,8-difluoro-2-trifluoromethoxynaphthalene
-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-methyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-ethyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-propyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-butyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-hexyl-transdecahydronaphthalene 6- (1,6-difluoro-7-trifluoromethoxynaphthalene
-3-yl) -2-heptyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (1 , 3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,3,8 -Trifluoro-2-trifluoromethoxynaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-trifluoromethoxynaphthalen-6-yl) -2- Hexyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-trifluoromethoxynaphthalene- 6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-methyl
-Transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-ethyl
-Transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-butyl
-Transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-difluoromethoxynaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6 -(2-Difluoromethoxynaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- ( 1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6 -(1-Fluoro-2-difluoromethoxynaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2-pentyl-to Nsdecahydronaphthalene 6- (1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1-fluoro-2-difluoromethoxynaphthalen-6-yl) -2- Heptyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl)- 2-ethyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl ) -2-Butyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaph Len-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-difluoromethoxy-3-fluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1,3-difluoro- 2-difluoromethoxynaphthalene-6
-Yl) -2-methyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-ethyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-propyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-butyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-pentyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-hexyl-transdecahydronaphthalene 6- (1,3-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoromethoxynaphthalen-3-yl) -2-methyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoromethoxynaphthalene -3-yl) -2-ethyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoromethoxynaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoro Methoxynaphthalen-3-yl) -2-butyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoromethoxynaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-7 -Difluoromethoxynaphthalen-3-yl) -2-hexyl-transdecahydronaphthalene 6- (1-fluoro-7-difluoromethoxynaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene 6- (1,8 -Difluoro-2- Difluoromethoxynaphthalene-6
-Yl) -2-methyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-ethyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-propyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-butyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-pentyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-hexyl-transdecahydronaphthalene 6- (1,8-difluoro-2-difluoromethoxynaphthalene-6
-Yl) -2-heptyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-methyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-ethyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-propyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-butyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-pentyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-hexyl-transdecahydronaphthalene 6- (1,6-difluoro-7-difluoromethoxynaphthalene-3
-Yl) -2-heptyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (1,3, 8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-propyl -Transdecahydronaphthalene 6- (1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2- Difluoromethoxynaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-2-difluoromethoxynaphthalen-6-yl) -2-hepti - trans-decahydronaphthalene

6- (2-chloronaphthalen-6-yl) -2-methyl
-Transdecahydronaphthalene 6- (2-chloronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-chloronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- ( 2-chloronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-chloronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-chloronaphthalen-6-yl ) -2-Hexyl-transdecahydronaphthalene 6- (2-chloronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2- Methyl-
Transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-hexyl- Transdecahydronaphthalene 6- (1-fluoro-2-chloronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-methyl-
Transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-hexyl- Transdecahydronaphthalene 6- (2-chloro-3-fluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluorona Phthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-chloro-1,3-difluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-7 -Chloronaphthalen-3-yl) -2-methyl-
Transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-butyl-
Transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-hexyl- Transdecahydronaphthalene 6- (1-fluoro-7-chloronaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chlorona Phthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,8-difluoro-7-chloronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1,6-difluoro -7-chloronaphthalen-3-yl) -2-methyl-transdecahydronaphthalene 6- (1,6-difluoro-7-chloronaphthalen-3-yl) -2-ethyl-transdecahydronaphthalene 6- (1 6,6-Difluoro-7-chloronaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1,6-difluoro-7-chloronaphthalen-3-yl) -2-butyl-transdecahydronaphthalene 6- (1,6-difluoro-7-chloronaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1,6-difluoro-7-chloronaphthalen-3-yl) -2-hexyl- Transdecahydronaphthalene 6- (1,6-difluoro-7-chloronaphthalen-3-yl) -2-heptyl-transdecahydro Naphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Methyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Ethyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Propyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Butyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Pentyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Hexyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-chloronaphthalen-6-yl) -2
-Heptyl-transdecahydronaphthalene

6- (2-cyanonaphthalen-6-yl) -2-methyl
-Transdecahydronaphthalene 6- (2-cyanonaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-cyanonaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- ( 2-cyanonaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-cyanonaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-cyanonaphthalen-6-yl ) -2-Hexyl-transdecahydronaphthalene 6- (2-cyanonaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2- Methyl-
Transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-hexyl- Transdecahydronaphthalene 6- (2-cyano-1-fluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-methyl-
Transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-ethyl-
Transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-butyl-
Transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-hexyl- Transdecahydronaphthalene 6- (2-cyano-3-fluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluorona Phthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-cyano-1,3-difluoronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1-fluoro-7 -Cyanonaphthalen-3-yl) -2-methyl-
Transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-ethyl-
Transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-butyl-
Transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-hexyl- Transdecahydronaphthalene 6- (1-fluoro-7-cyanonaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanona Phthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (1,8-difluoro-7-cyanonaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (1,6-difluoro -7-Cyanonaphthalen-3-yl) -2-methyl-transdecahydronaphthalene 6- (1,6-difluoro-7-cyanonaphthalen-3-yl) -2-ethyl-transdecahydronaphthalene 6- (1 , 6-Difluoro-7-cyanonaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (1,6-difluoro-7-cyanonaphthalen-3-yl) -2-butyl-transdecahydronaphthalene 6- (1,6-difluoro-7-cyanonaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6- (1,6-difluoro-7-cyanonaphthalen-3-yl) -2-hexyl- Transdecahydronaphthalene 6- (1,6-difluoro-7-cyanonaphthalen-3-yl) -2-heptyl-transdecahydro Naphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Methyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Ethyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Propyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Butyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Pentyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Hexyl-transdecahydronaphthalene 6- (1,3,8-trifluoro-7-cyanonaphthalen-6-yl) -2
-Heptyl-transdecahydronaphthalene

6- [2- (trifluoromethyl) naphthalene-6-
Yl] -2-methyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalen-6-yl] -2-ethyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalene-6- Yl] -2-propyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalen-6-yl] -2-butyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalene-6- Yl] -2-pentyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalen-6-yl] -2-hexyl-transdecahydronaphthalene 6- [2- (trifluoromethyl) naphthalene-6- Yl] -2-heptyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-methyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-ethyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-propyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-butyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-pentyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-hexyl-transdecahydronaphthalene 6- [1-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-heptyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-methyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-ethyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-propyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-butyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-pentyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-hexyl-transdecahydronaphthalene 6- [3-fluoro-2- (trifluoromethyl) naphthalene-6-
Yl] -2-heptyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-methyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-ethyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-propyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-butyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-pentyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-hexyl-transdecahydronaphthalene 6- [1,3-difluoro-2- (trifluoromethyl) naphthalene
-6-yl] -2-heptyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-methyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-ethyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-propyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-butyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-pentyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-hexyl-transdecahydronaphthalene 6- [1-fluoro-7- (trifluoromethyl) naphthalene-3-
Yl] -2-heptyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-methyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-ethyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-propyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-butyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-pentyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-hexyl-transdecahydronaphthalene 6- [1,8-difluoro-7- (trifluoromethyl) naphthalene
-6-yl] -2-heptyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-methyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-ethyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-propyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-butyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-pentyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-hexyl-transdecahydronaphthalene 6- [1,6-difluoro-7- (trifluoromethyl) naphthalene
-3-yl] -2-heptyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl) naphthalen-6-yl] -2-methyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl) naphthalen-6-yl] -2-ethyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl ) Naphthalen-6-yl] -2-propyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl) naphthalen-6-yl] -2-butyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl) naphthalen-6-yl] -2-pentyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoro Fluoromethyl) naphthalen-6-yl] -2-hexyl-transdecahydronaphthalene 6- [1,3,8-trifluoro-7- (trifluoromethyl) naphthalene-6-i ] -2-heptyl - trans-decahydronaphthalene

Methyl 6- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 6- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 6 -(6-propyl-transdecahydronaphthalen-2-yl)
Methyl naphthalene-2-carboxylate 6- (6-butyl-transdecahydronaphthalen-2-yl) methyl naphthalene-2-carboxylate 6- (6-pentyl-transdecahydronaphthalen-2-yl)
Methyl naphthalene-2-carboxylate 6- (6-hexyl-transdecahydronaphthalen-2-yl)
Methyl naphthalene-2-carboxylate 6- (6-heptyl-transdecahydronaphthalen-2-yl)
Methyl naphthalene-2-carboxylate 1-fluoro-6- (6-methyl-transdecahydronaphthalen-2-yl) methyl naphthalene-2-carboxylate 1-fluoro-6- (6-ethyl-transdecahydronaphthalene- Methyl 2-yl) naphthalene-2-carboxylate 1-Fluoro-6- (6-propyl-transdecahydronaphthalen-2-yl) methyl naphthalene-2-carboxylate 1-fluoro-6- (6-butyl-trans Methyl decahydronaphthalen-2-yl) naphthalene-2-carboxylate 1-Fluoro-6- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1-fluoro-6- (6 Methyl 1-fluoro-6- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 3-fluoro-hexyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 6- (6-methyl-transdecahydronaphthale Methyl 2-fluoro-2-naphthalene-2-carboxylate 3-fluoro-6- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 3-fluoro-6- (6-propyl- Transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate methyl 3-fluoro-6- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate methyl 3-fluoro-6- ( Methyl 6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 3-fluoro-6- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 3-fluoro Methyl 1,6-difluoro-6- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl carboxylate 1,3-difluoro-6- (6-ethyl-transdeca Methyl hydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,3-difluoro-6- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,3-difluoro-6 Methyl 1,3-difluoro-6- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate-(6-butyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,3-difluoro-6- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,3-difluoro-6- (6-heptyl-transdecahydronaphthalene-2- Methyl 1-fluoro-7- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1-fluoro-7- (6-ethyl-transdecahydromethyl) naphthalene-2-carboxylate Naphthalene-2-yl) methyl naphthalene-3-carboxylate 1-fluoro B-Methyl 7- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1-fluoro-7- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylic acid Methyl 1-fluoro-7- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate Methyl 1-fluoro-7- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene Methyl-3-carboxylate 1-fluoro-7- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1,2-difluoro-7- (6-methyl-transdecahydronaphthalene Methyl 2--2-yl) naphthalene-3-carboxylate 1,2-difluoro-7- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1,2-difluoro-7- ( 6-propyl-transdecahydronaphthalen-2-yl) naphthalene-3-cal Methyl bonate 1,2-difluoro-7- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate Methyl 1,2-difluoro-7- (6-pentyl-transdecahydronaphthalene- Methyl 2-yl) naphthalene-3-carboxylate 1,2-Difluoro-7- (6-hexyl-transdecahydronaphthalen-2-yl) methyl 1,2-difluoro-7- (6 Methyl 1-fluoro-3- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1-fluoro-Heptyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate Methyl 3- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate Methyl 1-fluoro-3- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1-fluoro-3- (6-butyl-transdecahydronaphthalene-2 Methyl 1-fluoro-3- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1-fluoro-3- (6-hexyl-transdeca-yl) naphthalene-7-carboxylate Methyl hydronaphthalen-2-yl) naphthalene-7-carboxylate 1-Fluoro-3- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,8-difluoro-6- ( Methyl 6-methyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,8-difluoro-6- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1 Methyl 1,8-difluoro-6- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,8-difluoro-6- (6-butyl-transdecahydronaphthalen-2-yl) Methyl naphthalene-2-carboxylate 1,8-difluoro-6- (6-pentyl-to Msdecahydronaphthalen-2-yl) naphthalene-2-carboxylate methyl 1,8-difluoro-6- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate methyl 1,8-difluoro Methyl 1,6-difluoro-3- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl carboxylate 1,6-difluoro-3- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-7-methyl carboxylate 1,6-difluoro-3- (6-propyl-transdecahydronaphthalene- Methyl 2-yl) naphthalene-7-carboxylate 1,6-difluoro-3- (6-butyl-transdecahydronaphthalen-2-yl) methyl naphthalene-7-carboxylate 1,6-difluoro-3- (6 -Pentyl-transdecahydronaphthalen-2-yl) naphthalene-7-carvone Methyl 1,6-difluoro-3- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,6-difluoro-3- (6-heptyl-transdecahydronaphthalene-2 -Yl) methyl naphthalene-7-carboxylate 1,3,8-trifluoro-6- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,3,8-trifluoromethyl Methyl 1,6- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,3,8-trifluoro-6- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene Methyl-2-carboxylate 1,3,8-trifluoro-6- (6-butyl-transdecahydronaphthalen-2-yl) methyl naphthalene-2-carboxylate 1,3,8-trifluoro-6- ( Methyl 6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,3,8-trifluoro-6- (6-hexyl Methyl trans-decahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,3,8-trifluoro-6- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 3 -Fluoro-2- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate methyl 3-fluoro-2- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-6- Methyl carboxylate 3-fluoro-2- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-6-methyl carboxylate 3-fluoro-2- (6-butyl-transdecahydronaphthalen-2-yl) Methyl naphthalene-6-carboxylate 3-fluoro-2- (6-pentyl-transdecahydronaphthalen-2-yl) methyl naphthalene-6-carboxylate 3-fluoro-2- (6-hexyl-transdecahydronaphthalene- 2-yl) naphthalene-6-carboxylic acid methyl 3-phthalate Fluoro-2- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,7-difluoro-6- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-2 1,7-difluoro-6- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxymethyl 1,7-difluoro-6- (6-propyl-transdecahydronaphthalene Methyl 2,7-difluoro-6- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1,7-difluoro-6- ( Methyl 6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate Methyl 1,7-difluoro-6- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-2-carboxylate 1 , 7-Difluoro-6- (6-heptyl-transdecahydronaphthalene-2-i Methyl naphthalene-2-carboxylate 1,2-difluoro-3- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,2-difluoro-3- (6-ethyl- Transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate methyl 1,2-difluoro-3- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate methyl 1,2-difluoro Methyl 1,3-difluoro-3- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate-3- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate Methyl carboxylate 1,2-difluoro-3- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-7-methyl carboxylate 1,2-difluoro-3- (6-heptyl-transdecahydronaphthalene- Methyl 2-yl) naphthalene-7-carboxylate 1,2,8-trifluoro-3- (6-meth Methyl 1,2-, 8-trifluoro-3- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate Methyl 1,2,8-trifluoro-3- (6-propyl-trans-decahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,2,8-trifluoro-3- (6-butyl-transdeca Methyl hydronaphthalen-2-yl) naphthalene-7-carboxylate 1,2,8-trifluoro-3- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,2, Methyl 8-trifluoro-3- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-7-carboxylate 1,2,8-trifluoro-3- (6-heptyl-transdecahydronaphthalene-2 -Yl) methyl naphthalene-7-carboxylate 1-fluoro-2- (6-methyl-transdecahydronaphthalene-2- M-naphthalene-6-carboxylate 1-fluoro-2- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1-fluoro-2- (6-propyl-transdecahydro Methyl naphthalene-6-carboxylate 1-fluoro-2- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1-fluoro-2- (6-pentyl) naphthalene-6-carboxylate Methyl 1-fluoro-2- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1-fluoro-2-methyltrans-decahydronaphthalen-2-yl) naphthalene-6-carboxylate Methyl (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate Methyl 1,7-difluoro-2- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,7-difluoro-2- (6-ethyl-transdecahydride Ronaphthalen-2-yl) naphthalene-6-carboxylate methyl 1,7-difluoro-2- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,7-difluoro-2 Methyl 1,6-difluoro-2- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate-(6-butyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate Methyl 1,7-difluoro-2- (6-hexyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate Methyl 1,7-difluoro-2- (6-heptyl-transdecahydronaphthalene-2- Methyl 1,8-difluoro-2- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,8-difluoro-2- (6-ethyl) naphthalene-6-carboxylate -Transdecahydronaphthalen-2-yl) naphthalene-6-carboxylic acid methyl ester 1,8-di Methyl fluoro-2- (6-propyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,8-difluoro-2- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-6 -Methyl carboxylate 1,8-difluoro-2- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-6-methyl carboxylate 1,8-difluoro-2- (6-hexyl-transdecahydronaphthalene Methyl-2-yl) naphthalene-6-carboxylate 1,8-difluoro-2- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-6-carboxylate 1,2,8-trifluoro- Methyl 7- (6-methyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1,2,8-trifluoro-7- (6-ethyl-transdecahydronaphthalen-2-yl) naphthalene- Methyl 3-carboxylate 1,2,8-trifluoro-7- (6-propyl-transdecahydrona Methyl 1,2-, 8-trifluoro-7- (6-butyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1,2,8 -Trifluoro-7- (6-pentyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate 1,2,8-trifluoro-7- (6-hexyl-transdecahydronaphthalen-2- Methyl 1,2,8-trifluoro-7- (6-heptyl-transdecahydronaphthalen-2-yl) naphthalene-3-carboxylate

Example 5 Synthesis of 6- (6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene (I-5)

[0337]

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(5-a) Synthesis of 6-propyl-transdecahydronaphthalen-2-ol 25 g of 6-propyl-transdecahydronaphthalen-2-one
Is reduced in the same manner as (1-a), to give 6 g of a pale yellow oily substance of 6-propyl-transdecahydronaphthalen-2-ol.
I got (5-b) Synthesis of 2-bromo-6-propyl-transdecahydronaphthalene 18 g of 6-propyl-transdecahydronaphthalen-2-ol obtained in (5-a) was cooled to 0 ° C. in 100 mL of dichloromethane. To this solution was added dropwise a solution of 9 g of phosphorus tribromide in 50 mL of dichloromethane. After stirring at room temperature for 3 hours, water was added, the organic layer was separated, washed with a saturated aqueous solution of sodium hydrogen carbonate, water and saturated saline in this order, dried over anhydrous sodium sulfate, and the solvent was distilled off. Purification by silica gel column chromatography (hexane) gave 5 g of 2-bromo-6-propyl-transdecahydronaphthalene as a pale yellow oil. (5-c) Synthesis of 6- (6-fluoro-1,4-dihydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene In the same manner as in (1-d), obtained by (5-b). 2-bromo-6-propyl-
A Grignard reagent was prepared from 5 g of transdecahydronaphthalene, reacted with 4 g of 6-fluoro-1,2,3,4-tetrahydronaphthalen-2-one, and dehydrated to give 6-
3 g of a pale yellow solid of (6-fluoro-1,4-dihydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene was obtained. (5-d) Synthesis of 6- (6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (obtained in (5-c) 6-fluoro-1,4-dihydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene
By catalytic hydrogen reduction of 3 g in the same manner as in (1-e), 6- (6-
Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-
1 g of white solid of propyl-transdecahydronaphthalene
I got

The following compounds are obtained in the same manner.

6- (6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-fluoro-1,2,3,4-tetrahydro Naphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6 -Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)- 2-hexyl-transdecahydronaphthalene 6- (6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (5,6-difluoro-1, 2,3,4-tetrahydronaphthalene-2
-Yl) -2-methyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-ethyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-propyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-butyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-pentyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-hexyl-transdecahydronaphthalene 6- (5,6-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-heptyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-methyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-ethyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-propyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-butyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-pentyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-hexyl-transdecahydronaphthalene 6- (6,7-difluoro-1,2,3,4-tetrahydronaphthalene-2
-Yl) -2-heptyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2, 3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2- Butyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5,6,7 -Trifluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalene -2-yl) -2-heptyl-transdeca Dronaphthalene 6- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-trifluoromethoxy-1,2,3, 4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydro Naphthalene 6- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-trifluoromethoxy-1,2,3,4 -Tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-tra 1- (5-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-6- Trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydro Naphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdeca Hydronaphthalene 6- (5-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-6-trifluoro Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (5- Fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy-1,2,3 , 4-Tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2- Ethyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (7-fluoro- 6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy-1,2,3,4 -Tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy -1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-6-trifluoromethoxy-1,2,3,4-tetrahydronaphthalene-2 -Yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-6-trifluoromethoxy-1,2,3,4-
Tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetrahydronaphthalene-2 -Yl) -2-propyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-difluoro Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)- 2-hexyl-transdecahydronaphthalene 6- (6-difluoromethoxy-1,2,3,4-tetra Hydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (5-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdeca Hydronaphthalene 6- (5-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-6-difluoromethoxy- 1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl ) -2-Butyl-transdecahydronaphthalene 6- (5-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5 -Fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-tolan Decahydronaphthalene 6- (5-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (7-fluoro-6-difluoromethoxy -1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalene-2- Yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- ( 7-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro-6-difluoromethoxy-1,2,3 , 4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-6-diph Oromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalene-2 -Yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoro Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalene 2-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetra Hydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl- Transdecahydronaphthalene 6- (5,7-difluoro-6-difluoromethoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene

6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydro (Naphthalen-2-yl)
2-ethyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)
2-propyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)
2-butyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)
2-pentyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)
2-hexyl-transdecahydronaphthalene 6- (6-chloro-1,2,3,4-tetrahydronaphthalen-2-yl)
2-heptyl-transdecahydronaphthalene 6- (6-chloro-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-chloro -5-Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-chloro-5-fluoro-1,2,3,4-tetrahydronaphthalene -2-yl) -2-propyl-transdecahydronaphthalene 6- (6-chloro-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6 -(6-chloro-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-chloro-5-fluoro-1,2,3 , 4-Tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-chloro-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl- Trance Cahydronaphthalene 6- (6-chloro-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-chloro-7-fluoro-1 , 2,3,4-Tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-chloro-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)- 2-propyl-transdecahydronaphthalene 6- (6-chloro-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-chloro- 7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-chloro-7-fluoro-1,2,3,4-tetrahydronaphthalene- 2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-chloro-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro- 1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1,2,3,4-tetrahydronaphthalene-2- Yl) -2-propyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1, 2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-chloro-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) 2-heptyl-transdecahydronaphtha Len

6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydro (Naphthalen-2-yl)
2-ethyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)
2-propyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)
2-butyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)
2-pentyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)
2-hexyl-transdecahydronaphthalene 6- (6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)
2-heptyl-transdecahydronaphthalene 6- (6-cyano-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-cyano -5-Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-cyano-5-fluoro-1,2,3,4-tetrahydronaphthalene 2-yl) -2-propyl-transdecahydronaphthalene 6- (6-cyano-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6 -(6-cyano-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-cyano-5-fluoro-1,2,3 , 4-Tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-cyano-5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl- Trance Cahydronaphthalene 6- (6-cyano-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-cyano-7-fluoro-1 , 2,3,4-Tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-cyano-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)- 2-propyl-transdecahydronaphthalene 6- (6-cyano-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-cyano- 7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-cyano-7-fluoro-1,2,3,4-tetrahydronaphthalene- 2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-cyano-7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaph Talene 6- (6-cyano-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-cyano-5,7-difluoro -1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-cyano-5,7-difluoro-1,2,3,4-tetrahydronaphthalene-2 -Yl) -2-propyl-transdecahydronaphthalene 6- (6-cyano-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6 -(6-cyano-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-cyano-5,7-difluoro-1 , 2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-cyano-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl ) -2-Heptyl-transdecahydro Naphthalene

6- [6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trifluoromethyl) -1 , 2,3,4-Tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl]- 2-propyl-transdecahydronaphthalene 6- [6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (tri Fluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalene- 2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdeca Dronaphthalene 6- [5-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [5-fluoro-6- (Trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5-fluoro-6- (trifluoromethyl) -1,2,3 , 4-Tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl]- 2-butyl-transdecahydronaphthalene 6- [5-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [ 5-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [5-fluoro-6- (to Fluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1,2,3,4 -Tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2- Ethyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [7- Fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1 , 2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydrido Naphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [7-fluoro-6- (trifluoromethyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl- Transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trifluoromethyl) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene

Methyl 2- (6-methyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-ethyl-transdecahydronaphthalen-2-yl) Il)-
Methyl 1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-propyl-transdecahydronaphthalen-2-yl)
Methyl -1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-butyl-transdecahydronaphthalen-2-yl)-
Methyl 1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-pentyl-transdecahydronaphthalen-2-yl)
Methyl -1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-hexyl-transdecahydronaphthalen-2-yl)
Methyl -1,2,3,4-tetrahydronaphthalene-6-carboxylate 2- (6-heptyl-transdecahydronaphthalen-2-yl)
Methyl -1,2,3,4-tetrahydronaphthalene-6-carboxylate 5-fluoro-2- (6-methyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6 Methyl 5-carboxylate 5-fluoro-2- (6-ethyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-methyl 5-carboxylate 5-fluoro-2- (6- Propyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate methyl 5-fluoro-2- (6-butyl-transdecahydronaphthalen-2-yl) -1 Methyl 2,2,3,4-tetrahydronaphthalene-6-carboxylate 5-fluoro-2- (6-pentyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylic acid Methyl 7-fluoro-2- (6-hexyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate Methyl 2--2- (6-heptyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate 7-fluoro-2- (6-methyl-transdecahydronaphthalene) 2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate methyl 7-fluoro-2- (6-ethyl-transdecahydronaphthalen-2-yl) -1,2,3,4 Methyl-tetrahydronaphthalene-6-carboxylate 7-fluoro-2- (6-propyl-transdecahydronaphthalen-2-yl) -1,2,3,4-methyl methyl 7-fluoro-tetrahydronaphthalene-6-carboxylate Methyl 2- (6-butyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate 7-fluoro-2- (6-pentyl-transdecahydronaphthalene-2 -Yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate methyl 7-fluoro-2- (6-hexyl-transdecahydronaphthalen-2-yl) -1, Methyl 2,3,4-tetrahydronaphthalene-6-carboxylate 7-fluoro-2- (6-heptyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylic acid Methyl 7-fluoro-2- (6-heptyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate Methyl 5,7-difluoro-2- (6-methyl -Transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-carboxylate methyl 5,7-difluoro-2- (6-ethyl-transdecahydronaphthalen-2-yl)- Methyl 1,2,3,4-tetrahydronaphthalene-6-carboxylate 5,7-difluoro-2- (6-propyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene- 6-
Methyl carboxylate 5,7-difluoro-2- (6-butyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-methyl carboxylate 5,7-difluoro-2- (6-pentyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-
Methyl carboxylate 5,7-difluoro-2- (6-hexyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-
Methyl carboxylate 5,7-difluoro-2- (6-heptyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-6-
Methyl carboxylate 5-fluoro-3- (6-methyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-methyl carboxylate 5-fluoro-3- (6-ethyl -Transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-carboxylate methyl 5-fluoro-3- (6-propyl-transdecahydronaphthalen-2-yl) -1, Methyl 2,3,4-tetrahydronaphthalene-7-carboxylate 5-fluoro-3- (6-butyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-carboxylic acid Methyl 5-fluoro-3- (6-pentyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-carboxylate Methyl 5-fluoro-3- (6-hexyl-trans Decahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-carboxylate methyl 5-fluoro-3- (6-heptyl-transdecahi Dronaphthalen-2-yl) -1,2,3,4-methyltetrahydronaphthalene-7-carboxylate 5,6-difluoro-3- (6-methyl-transdecahydronaphthalen-2-yl) -1,2 Methyl 5,3,4-tetrahydronaphthalene-7-carboxylate 5,6-difluoro-3- (6-ethyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-carboxy Methyl 5,6-difluoro-3- (6-propyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-
Methyl carboxylate 5,6-difluoro-3- (6-butyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-methyl carboxylate 5,6-difluoro-3- (6-pentyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalen-7-
Methyl carboxylate 5,6-difluoro-3- (6-hexyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-
Methyl carboxylate 5,6-difluoro-3- (6-heptyl-transdecahydronaphthalen-2-yl) -1,2,3,4-tetrahydronaphthalene-7-
Methyl carboxylate

6- [6- (3-Butenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1 , 2,3,4-tetrahydronaphthalene-2
-Yl] -2-ethyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1,2,3,4-tetrahydronaphthalene-2
-Yl] -2-propyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1,2,3,4-tetrahydronaphthalene-2
-Yl] -2-butyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1,2,3,4-tetrahydronaphthalene-2
-Yl] -2-pentyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1,2,3,4-tetrahydronaphthalene-2
-Yl] -2-hexyl-transdecahydronaphthalene 6- [6- (3-butenyl) -1,2,3,4-tetrahydronaphthalene-2
-Yl] -2-heptyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydro Naphthalene 6- [6- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5-Fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5-fluoro-1,2,3, 4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2 -Pentyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6 -(3-butenyl) -5-fluoro-1,2,3,4-tetrahydride Ronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl -Transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- ( 3-butenyl) -7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1, 2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1,2,3,4-tetrahydronaphthalene-2- Yl] -2-pentyl-transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (3-butenyl) -7-fluoro-1,2 , 3,4-Tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalene-2 -Yl] -2-methyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-trans Decahydronaphthalene 6- [6- (3-butenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- ( 3-butenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5,7- Difluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (3-butenyl) -5,7-difluoro-1,2,3,4 -Tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaph 6- [6- (3-butenyl) -5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (3- (Butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5-fluoro-1,2, 3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] 2-propyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5- Fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-hexyl-tra Sdecahydronaphthalene 6- [7- (3-butenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (3 -Butenyl) -5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro -1,2,3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro-1,2,3,4- Tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2 -Butyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro-1,2,3,4-tetrahydride Naphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [7- (3-butenyl) -5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2- Heptyl-transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trans -3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -1,2,3,4 -Tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl- Transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trans-3 -Pente ) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalene -2-yl] -2-heptyl-transdecahydronaphthalene 6- [5-fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl -Transdecahydronaphthalene 6- [5-fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5 -Fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5-fluoro-6- (trans-3 -Pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [5-fluoro-6- (trans-3-pentenyl) -1,2,3 , 4-tetrahydronaphthale -2-yl] -2-pentyl-transdecahydronaphthalene 6- [5-fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl -Transdecahydronaphthalene 6- [5-fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7 -Fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [7-fluoro-6- (trans-3 -Pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [7-fluoro-6- (trans-3-pentenyl) -1,2,3 , 4-Tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [7-fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl ] -2-butyl-to Nsdecahydronaphthalene 6- [7-Fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [7- Fluoro-6- (trans-3-pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [7-fluoro-6- (trans-3- Pentenyl) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2, 3,
4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (trans-3-pentenyl) -1,2,3,
4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] 2-methyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (trans-3 -Pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1 , 2,3,4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthal 3-Nyl] -2-hexyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2- Heptyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [7- (trans-3-pentenyl) -5,6-difluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene

6- (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-transdecahydronaphthalene 6- (6-methoxy-1,2,3,4-tetrahydro Naphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (6 -Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)- 2-pentyl-transdecahydronaphthalene 6- (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-methoxy-1,2, 3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl -Transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy -1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl ) -2-Butyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (5- Fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydro Naphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-tra 1- (5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-6-methoxy- 1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (7-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) 2-butyl-transdecahydronaphthalene 6- (7-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro -6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalene 2-yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-methyl-tolan Sdecahydronaphthalene 6- (5,7-difluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro- 6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-6-methoxy-1,2,3,4-tetrahydro Naphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-pentyl-transdeca Hydronaphthalene 6- (5,7-difluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-6- Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (7-methoxy-5-fluoro-1,2,3,4-tetrahydronaphthalene-3- Ill) 2-methyl-transdecahydronaphthalene 6- (7-methoxy-5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-ethyl-transdecahydronaphthalene 6- (7-methoxy -5-Fluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (7-methoxy-5-fluoro-1,2,3,4-tetrahydronaphthalene -3-yl) -2-butyl-transdecahydronaphthalene 6- (7-methoxy-5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-pentyl-transdecahydronaphthalene 6 -(7-Methoxy-5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-hexyl-transdecahydronaphthalene 6- (7-methoxy-5-fluoro-1,2,3 , 4-Tetrahydronaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene 6- (7-methoxy-5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2- Methyl-transdecahydronaphthalene 6- (7-methoxy-5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-ethyl-transdecahydronaphthalene 6- (7-methoxy- 5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-propyl-transdecahydronaphthalene 6- (7-methoxy-5,6-difluoro-1,2,3,4 -Tetrahydronaphthalen-3-yl) -2-butyl-transdecahydronaphthalene 6- (7-methoxy-5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-pentyl- Transdecahydronaphthalene 6- (7-methoxy-5,6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-hexyl-transdecahydronaphthalene 6- (7-methoxy-5, 6-difluoro-1,2,3,4-tetrahydronaphthalen-3-yl) -2-heptyl-transdecahydronaphthalene

6- [6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalene-2- Yl] -2-propyl-transdecahydronaphthalene 6- [6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [ 6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (2-propenyloxy) -1,2,3 , 4-Tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl -Transdecahide Naphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2 , 3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalene-2- Yl] -2-butyl-transdecahydronaphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydro Naphthalene 6- [5-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [5-fluoro-6- (2-propenyl Oxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyloxy) -1,2,3,4 -Tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2 -Ethyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [ 7-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyl) Oxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyloxy) -1,2,3,4 -Tetrahydronaphthalene-2- Yl] -2-hexyl-transdecahydronaphthalene 6- [7-fluoro-6- (2-propenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydro Naphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [5,7-difluoro-6- (2-propenyloxy) -1,2,3,4-
Tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2- Methyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7 -(2-propenyloxy) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5- Fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5-fluoro-1,2,3,4- Tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2- Hexy Le-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5-fluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene 6- [7 -(2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [7- (2-propenyloxy) -5,6-difluoro-1,2,3,4-
Tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene

6- [6- (trans-2-butenyloxy) -1,2,
3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2 -Ethyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- ( Trans-2-butenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -1,2,3, 4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl -Transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -1,2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahi B naphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -7-fluoro-1,2,3,
4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-methyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-ethyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-propyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-butyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-pentyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-hexyl-transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -5,7-difluoro-1,
2,3,4-tetrahydronaphthalen-2-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5-fluoro-1,2,3,
4-tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-propyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [7- (trans-2-butenyloxy) -5,6-difluoro-1,
2,3,4-tetrahydronaphthalen-3-yl] -2-heptyl-transdecahydronaphthalene

6- [5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-methyl-transdecahydronaphthalene 6- [5,6,7-trifluoro -1,2,3,4-tetrahydronaphthalen-3-yl] -2-ethyl-transdecahydronaphthalene 6- [5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalene-3- Yl] -2-propyl-transdecahydronaphthalene 6- [5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-butyl-transdecahydronaphthalene 6- [ 5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-pentyl-transdecahydronaphthalene 6- [5,6,7-trifluoro-1,2,3 , 4-Tetrahydronaphthalen-3-yl] -2-hexyl-transdecahydronaphthalene 6- [5,6,7-trifluoro-1,2,3,4-tetrahydronaphthalen-3-yl] -2-heptyl -Transdecahydronaphthalene

Example 6 Synthesis of 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-vinyl-transdecahydronaphthalene (I-6)

[0351]

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(6-a) 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -1,2,3,4,7,8,9,10-transoctahydro Synthesis of naphthalen-2-one ethylene acetal In the same manner as in (1-d), 11 g of decahydronaphthalene-2,6-dione monoethylene acetal was added to 6-bromo-2-propyl-1,2,3,4
6- (2-propyl-1,2,3,4-tetrahydronaphthalene-6- by reacting with a Grignard reagent prepared from -tetrahydronaphthalene, dehydrating and reacetalizing
Il) -1,2,3,4,7,8,9,10-Transoctahydronaphthalen-2-one 16 g of a pale yellow solid of ethylene acetal was obtained. (6-b) Synthesis of 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalen-2-one ethylene acetal 6 obtained in (6-a) 16 g of-(2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -1,2,3,4,7,8,9,10-transoctahydronaphthalen-2-one ethylene acetal (1-
By catalytic hydrogen reduction in the same manner as in e), 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalen-2-one a pale yellow solid of ethylene acetal 14 g I got (6-c) Synthesis of 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalen-2-one 6- (obtained in (6-b) 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalene-2-
By deacetalizing 14 g of onethylene acetal in the same manner as (1-c), 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalene-2- 11 g of a pale yellow solid were obtained. (6-d) Synthesis of 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalene-2-carbaldehyde 6- obtained in (6-c) (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalene-2-
A solution of 11 g of ON in 100 mL of THF was added to 17 g of methoxymethyltriphenylphosphonium chloride and 6 g of potassium t-butoxide in THF.
It was added dropwise to the Wittig reagent prepared in 90 mL while cooling it to 10 ° C. or lower. After returning to room temperature and stirring for 4 hours,
Water and hexane were added, the organic layer was separated, washed with water, and the solvent was distilled off. The obtained pale yellow solid was dissolved in 130 mL of THF, 100 mL of 10% hydrochloric acid was added, and the mixture was heated under reflux for 3 hours. After returning to room temperature, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, and a saturated aqueous solution of sodium hydrogen carbonate was added,
After washing with water and saturated saline in this order, the solvent was distilled off. The obtained pale yellow solid was dissolved in 120 mL of methanol, and 20 mL of a 10% aqueous sodium hydroxide solution was added while cooling to 10 ° C. or lower. After stirring for 2 hours, the temperature was returned to room temperature, the solvent was distilled off, and the obtained pale yellow solid was washed with water, recrystallized from hexane, and treated with 6- (2
-Propyl-1,2,3,4-tetrahydronaphthalen-6-yl)-
8 g of a pale yellow solid of transdecahydronaphthalene-2-carbaldehyde was obtained. (6-e) Synthesis of 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-vinyl-transdecahydronaphthalene 6- (obtained in (6-d) 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -transdecahydronaphthalene-2-
A solution of 8 g of carbaldehyde in 45 mL of THF was prepared from 9 g of methyltriphenylphosphonium bromide and 4 g of potassium t-butoxide.
In a Wittig reagent prepared in 50 mL of THF, 1
The solution was added dropwise while cooling to 0 ° C or lower. After returning to room temperature and stirring for 3 hours, water and hexane were added, the organic layer was separated, washed with water, and the solvent was distilled off. Purified by silica gel column chromatography (hexane) and recrystallized from ethanol
(2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl)
4-g white solid of 2-vinyl-transdecahydronaphthalene
I got

The following compounds are obtained in the same manner.

6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydro (Naphthalene-6-yl)
2-ethyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-hexyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-heptyl-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-methoxy-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-ethoxy-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyloxy-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyloxy-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyloxy-transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (3-butenyl) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-methyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-ethyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-hexyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-heptyl-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-methoxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-ethoxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyloxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyloxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyloxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-hexyloxy-transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (3-butenyl) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2 -Propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-pentyl-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-propyl-1,2, 3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-tolan Decahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- ( 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Hexyloxy-transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-propyl 1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -Transdecahydronaphthalene 6- (2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-propyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalene-6 -Il)
2-methyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-ethyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-hexyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-heptyl-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-methoxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-ethoxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-propyloxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-butyloxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2-hexyloxy-transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-butyl-1,2,3,4-tetrahydronaphthalen-6-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Propyl-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-pentyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-trans Decahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetra Hydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- ( 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Butyloxy-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-pentyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- ( Trans-1-propenyl) -transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl ) -Transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-pentyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalene-6- Yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-pentyl-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-hexyl-1,2, 3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-tolan Decahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- ( 2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Hexyloxy-transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-hexyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -Transdecahydronaphthalene 6- (2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-hexyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2-methyl-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-heptyl- 1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Hexyl-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-heptyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-trans Decahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthal 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (2 -Heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -Transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-hepty -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroe (Tenyl) -transdecahydronaphthalene

6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5-fluoro- 2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5-full Oro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-1-propenyl) -transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdeca Hid Naphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5-fluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (5-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethene (Tenyl) -transdecahydronaphthalene

6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-ethyl- 5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-ethyl 5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Hexyloxy-transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahi Dronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-ethyl-5- Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-ethyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5-fluoro- 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaph 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5-fluoro-2 -Propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyloxy-transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (tran 1-propenyl) -transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5-fluoro-2-propyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (5-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdeca Hydronaphthalene

6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-butyl- 5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-buty 5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Hexyloxy-transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahi Dronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-5- Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-butyl-5-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5-fluoro- 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphne Talene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5-fluoro-2 -Pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (tran 1-propenyl) -transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(5-Fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5-fluoro-2-pentyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (5-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdeca Hydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyl-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydride Naphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (t 1-propenyl) -transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5-fluoro-2- Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(2-fluoroethenyl) -transdecahydronaphthalene 6- (5-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl ) -Tran Decahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdeca Dronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyloxy-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (trans-1-propenyl) -transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -trans Decahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5-fluoro -2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (5-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2- Difluoroethenyl) -to Nsu decahydronaphthalene

6- (7-Fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro- 2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7-full Oro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-1-propenyl) -transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdeca Hid Naphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (7-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethyl (Tenyl) -transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2 -Ethyl-1,2,3,4-tetra Hydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydro Naphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Hexyl-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7-fluoro-2- Ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2-ethoxy-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (7-Fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3, 4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy -Transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7 -Fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2, 3, 4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -Transdecahydronaphthalene 6- (7-fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (7 -Fluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (7-fluoro-2-propyl- 1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl- Transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (7-fluoro-2-propyl- 1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) 2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy- Lancedecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (7-fluoro-2-propyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2-Pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- ( 7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7-fluoro-2-propyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-te Trahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)- Transdecahydronaphthalene 6- (7-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (7- Fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-butyl- 7-Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-buty 7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Hexyloxy-transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahi Dronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-7- Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-butyl-7-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (7-Fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro- 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaph Talene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro-2 -Pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (tran 1-propenyl) -transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(7-Fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro-2-pentyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (7-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdeca Hydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyl-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydride Naphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (t 1-propenyl) -transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (7-Fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro-2- Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(2-Fluoroethenyl) -transdecahydronaphthalene 6- (7-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl ) -Tran Decahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdeca Dronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyloxy-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -trans Decahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7-fluoro -2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (7-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2- Difluoroethenyl) -to Nsu decahydronaphthalene

6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (8-fluoro- 2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyl-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (8-full Oro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2 , 3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-1-propenyl) -transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdeca Hid Naphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (8-fluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (8-fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethyl (Tenyl) -transdecahydronaphthalene

6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-ethyl- 8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-Echi -8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Hexyloxy-transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahi Dronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-ethyl-8- Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-ethyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (8-Fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (8-fluoro- 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphne Talene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (8-fluoro-2 -Propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (tran 1-propenyl) -transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(8-Fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (8-fluoro-2-propyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (8-fluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdeca Hydronaphthalene

6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (2-butyl- 8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (2-buty 8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydro Naphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydro Naphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Hexyloxy-transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahi Dronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-8- Fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- (2-butyl-8-fluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (8-Fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1 , 2,3,4-Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (8-fluoro- 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaph Talene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (8-fluoro-2 -Pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (tran 1-propenyl) -transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(8-Fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (8-fluoro-2-pentyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydro Naphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (8-fluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdeca Hydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyl-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (8-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2-hexyl-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydride Naphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (8-fluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (t 1-propenyl) -transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (8-Fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (8-fluoro-2- Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(2-Fluoroethenyl) -transdecahydronaphthalene 6- (8-fluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl ) -Tran Decahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1 , 2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-propyl-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (8-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-hexyl-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdeca Dronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -Propyloxy-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (8-fluoro- 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (trans-1-propenyl) -transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -trans Decahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (8-fluoro -2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl ) -2- (2-Fluoroethenyl) -transdecahydronaphthalene 6- (8-fluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2- Difluoroethenyl) -to Nsu decahydronaphthalene

6- (5,7-Difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydro Naphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene-6 -Il) -2-heptyl-transdeca Dronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2- Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-propyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydro Naphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2- Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3 , 4-tetrahydro Phthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (Trans-3-pentenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy)- Transdecahydronaphthalene 6- (5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- ( 5,7-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7- Difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl- Transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro- 2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydro Naphthalene-6-a ) -2-Methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- ( 5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,
4-tetrahydronaphthalen-6-yl) -2-pentyloxy-
Transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5,7-difluoro -2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)- Transdecahydronaph 6- (5,7-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (5,7 -Difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2- Propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl- 1,2,3,4-tetrahydronaphthalene-6- Yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- ( 5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-pro Pill-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1 -Propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6 -(5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5,7-difluoro -2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2 , 3,4-tetrahydro Futaren-6-yl) -2- (trans-2-butenyloxy) -
Transdecahydronaphthalene 6- (5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 5,7-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-butyl-5,7 -Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalene -6-yl) -2-propyl-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydro Naphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro -1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalene-6 -Il) -2-heptyl-transdeca Dronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-butyl-5,7- Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-propyloxy-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydro Naphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-5,7- Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalene Les 6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -Transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- ( 2-butyl-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-5,7 -Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-butyl-5,7-difluoro-1,2, 3,4-tetrahydronaphthalen-6-yl) -2- (2,2-diph Oroeteniru) - trans-decahydronaphthalene

6- (5,7-Difluoro-2-pentyl-1,2,3,4-
Tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-trans Decahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (5,7-difluoro-2 -Pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydro Naphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5,7-difluoro 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy -Transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (5,7-difluoro -2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- ( G 1-propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdeca Hydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (5, 7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl- 1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 5,7-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (5,7-difluoro -2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-trans Decahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-2 -Hexyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5, 7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaph Talene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2- Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(3-butenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl)- Transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5 , 7-difluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 5,7-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (5,7-difluoro 2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-trans Decahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (5,7-difluoro-2 -Heptyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-hexyl-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (5, 7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaph Talene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2- Heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(3-Butenyl) -transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl)- Transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (5 , 7-difluoro-2 -Heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 5,7-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (7,8-Difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7,8-difluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-propyl-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydro Naphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl -1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene-6 -Il) -2-heptyl-transdeca Dronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2- Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-propyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydro Naphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2- Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3 , 4-tetrahydro Phthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (Trans-3-pentenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy)- Transdecahydronaphthalene 6- (7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- ( 7,8-difluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2 -Methyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2- Methyl-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7,8- Difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl- Transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (7,8-difluoro- 2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydro Naphtha Len-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdeca Hydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2 -Ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-trans Decahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7,8-Difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2- Ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalene-6- Yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2 -Fluoroethenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-ethyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -Transdecahydronaphthalene 6- (7,8-difluoro-2-p Pill-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalene- 6-yl) -2-ethyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl- 1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalene-6- Yl) -2-hexyl-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7,8-Difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- ( 7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1, 2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalene-6 -Yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- ( 3-butenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdeca Hydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7,8 -Difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 7,8-difluoro-2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (2-butyl-7,8 -Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalene -6-yl) -2-propyl-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydro Naphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro -1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalene-6 -Il) -2-heptyl-transdeca Dronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (2-butyl-7,8- Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalene- 6- (yl) -2-propyloxy-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydro Naphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (2-butyl-7,8- Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalene Les 6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl)- 2- (3-butenyl) -transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -Transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- ( 2-butyl-7,8-difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (2-butyl-7,8 -Difluoro-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (2-butyl-7,8-difluoro-1,2, 3,4-tetrahydronaphthalen-6-yl) -2- (2,2-diph Oroeteniru) - trans-decahydronaphthalene

6- (7,8-Difluoro-2-pentyl-1,2,3,4-
Tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-ethyl-trans Decahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-transdecahydronaphthalene 6- (7,8-difluoro-2 -Pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2-pentyl-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyl-transdecahydro Naphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7,8-difluoro 2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyloxy -Transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaphthalene 6- (7,8-difluoro -2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4 -Tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- ( G 1-propenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (3-butenyl) -transdeca Hydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (7, 8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl- 1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 7,8-difluoro-2-pentyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (7,8-difluoro -2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-trans Decahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7,8-difluoro-2 -Hexyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-hexyl-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7, 8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaph Talene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2- Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(3-Butenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl)- Transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7 , 8-Difluoro-2 -Hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 7,8-difluoro-2-hexyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (7,8-difluoro -2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methyl-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4- Tetrahydronaphthalen-6-yl) -2-ethyl-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-propyl-trans Decahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyl-transdecahydronaphthalene 6- (7,8-difluoro-2 -Heptyl-1,2 , 3,4-Tetrahydronaphthalen-6-yl) -2-pentyl-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl)- 2-hexyl-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-heptyl-transdecahydronaphthalene 6- (7, 8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-methoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3 , 4-Tetrahydronaphthalen-6-yl) -2-ethoxy-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- Propyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-butyloxy-transdecahydronaph Talene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-pentyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2- Heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2-hexyloxy-transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalene -6-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2 -(3-butenyl) -transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-3-pentenyl)- Transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (7 , 8-Difluoro-2 -Heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (trans-2-butenyloxy)-
Transdecahydronaphthalene 6- (7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- ( 7,8-difluoro-2-heptyl-1,2,3,4-tetrahydronaphthalen-6-yl) -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

Example 7 Synthesis of 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-vinyl-transdecahydronaphthalene (I-7)

[0377]

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(7-a) 4- (3-propylidenebicyclo [4.4.
Synthesis of [0] decane-8-yl) cyclohexanone ethylene acetal By reacting 10 g of 4- (6-oxo-transdecahydronaphthalen-2-yl) cyclohexanone ethylene acetal with a Wittig reagent in the same manner as (6-e) , 4- (3-
9 g of a white solid of propylidenebicyclo [4.4.0] decane-8-yl) cyclohexanone ethylene acetal was obtained. (7-b) Synthesis of 4- (trans-6-propyl-transdecahydronaphthalen-2-yl) cyclohexanone ethylene acetal 4- (3-propylidenebicyclo [4.4.0] obtained in (7-a) Decane-8-yl) cyclohexanone ethylene acetal 9g
By catalytic hydrogen reduction in the same manner as in (1-e), 4- (trans-6-propyl-transdecahydronaphthalen-2-yl)
8 g of a pale yellow solid of cyclohexanone ethylene acetal was obtained. (7-c) Synthesis of 4- (trans-6-propyl-transdecahydronaphthalen-2-yl) cyclohexanone 4- (trans-6-propyl-transdecahydronaphthalene-2 obtained in (7-b) By deacetalizing 8 g of (-yl) cyclohexanone ethylene acetal in the same manner as (1-c), 6 g of a pale yellow solid of 4- (trans-6-propyl-transdecahydronaphthalen-2-yl) cyclohexanone was obtained. . Synthesis of (7-d) 6- (trans-6-propyl-transdecahydronaphthalen-2-yl) -4,4a, 5,6,7,8-hexahydro-3H-naphthalen-2-one (7-d 6 g of 4- (trans-6-propyl-transdecahydronaphthalen-2-yl) cyclohexanone obtained in c) was dissolved in 30 mL of toluene, and 15 mL of pyrrolidine was added. The mixture was heated and refluxed for 4 hours using a device equipped with a water separator until there was no more distilled water. While continuing heating, after distilling off pyrrolidine and toluene, return to room temperature, add 40 mL of toluene, and cool to 20 ° C or lower, while cooling to 8 mL of methyl vinyl ketone.
Was added dropwise over 5 minutes. After the dropwise addition, the mixture was heated under reflux for 2 hours and allowed to cool to room temperature. An aqueous solution obtained by mixing 3 g of sodium acetate, 10 mL of glacial acetic acid and 10 mL of water was added, and the mixture was heated under reflux for 2 hours and then allowed to cool to room temperature. The organic layer was separated, washed with water and the solvent was distilled off. 8 g of the obtained oil was dissolved in 40 mL of THF, and 30 mL of 3M hydrochloric acid was added. After heating under reflux for 5 hours, the temperature was returned to room temperature, the organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off to give 6- (trans-6-propyl-transdecahydronaphthalene-2). -Il) -4,4a,
8 g of a brown solid of 5,6,7,8-hexahydro-3H-naphthalen-2-one was obtained. (7-e) Synthesis of 6- (trans-6-propyl-transdecahydronaphthalen-2-yl) -transdecahydronaphthalen-2-one 6- (trans-6- obtained in (7-d) Propyl-transdecahydronaphthalen-2-yl) -4,4a, 5,6,7,8-hexahydro
8 g of -3H-naphthalen-2-one and 20 mL of t-butanol in THF
40mL solution, 2g of metallic lithium in 100mL of liquid ammonia
While dissolving, the solution was added dropwise while maintaining the internal temperature at -30 to -40 ° C. After the addition, stirring was continued for 30 minutes. After lithium ammonium was oxidized by adding solid ammonium chloride little by little, the temperature was raised to room temperature, and ammonia was distilled off. Water was added, extracted with toluene, the organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, the solvent was distilled off, purified by silica gel column chromatography (toluene), and recrystallized from hexane. 4 g of a pale yellow liquid of -6- (trans-6-propyl-transdecahydronaphthalen-2-yl) -transdecahydronaphthalen-2-one was obtained. (7-f) 6- (6-propyl-transdecahydronaphthalene-
Synthesis of 2-yl) -transdecahydronaphthalene-2-carbaldehyde 6- (6-propyl-transdecahydronaphthalen-2-yl) -transdecahydronaphthalen-2-one obtained in (7-e) By reacting 6 g with a Wittig reactant in the same manner as (6-d), 6 g of 6- (6-propyl-transdecahydronaphthalen-2-yl) -transdecahydronaphthalene-2-carbaldehyde was obtained as a pale yellow solid 4 g. I got (7-g) 6- (6-propyl-transdecahydronaphthalene-
Synthesis of 2- (yl) -2-vinyl-transdecahydronaphthalene 6- (6-propyl-transdecahydronaphthalen-2-yl) -transdecahydronaphthalene-2-carbaldehyde obtained in (7-f) By reacting 4 g with a Wittig reagent in the same manner as in (6-e), 2 g of 6- (6-propyl-transdecahydronaphthalen-2-yl) -2-vinyl-transdecahydronaphthalene white solid was obtained. Was.

The following compounds are obtained in the same manner.

6- (6-methyl-tetrahydronaphthalene-2-
Yl) -2-methyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2 -Propyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-pentyl-trans Decahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6 -(6-Methyl-tetrahydronaphthalen-2-yl) -2-methoxy-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6- Tyl-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-methyl-tetrahydro Naphthalen-2-yl) -2-pentyloxy-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalene- 2-yl) -2-vinyl-transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-methyl-tetrahydro Naphthalen-2-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthale 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (trans-2- (Butenyloxy) -transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-methyl-tetrahydronaphthalen-2-yl) -2- (2,2-
Difluoroethenyl) -transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-ethyl-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-propyl -Transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydro Naphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- ( 6-ethyl-tetrahydronaphthalen-2-yl) -2-methoxy-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthale 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- ( 6-ethyl-tetrahydronaphthalen-2-yl) -2-pentyloxy-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6- Ethyl-tetrahydronaphthalen-2-yl) -2-vinyl-transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- ( 6-ethyl-tetrahydronaphthalen-2-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -trans Decahydrona 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2- (trans-2 -Butenyloxy) -transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-ethyl-tetrahydronaphthalen-2-yl ) -2- (2,2-
Difluoroethenyl) -transdecahydronaphthalene

6- (6-propyl-tetrahydronaphthalene-2)
-Yl) -2-propyl-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl)- 2-pentyl-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-heptyl- Trans-decahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-methoxy-trans-decahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-ethoxy-trans-decahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-butyloxy-to Nsdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-pentyloxy-transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdeca Hydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (3 -
(Butenyl) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-propyl-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-butyl-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2 -Pentyl-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-hexyl-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-heptyl-trans Decahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-methoxy-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6 -(6-butyl-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahi Dronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-pentyloxy-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2-vinyl-transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdeca Hydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (trans-3 -Pentenyl) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (trans-2-bute (Roxy) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-butyl-tetrahydronaphthalen-2-yl) -2- (2,2-
Difluoroethenyl) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-pentyl-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-hexyl -Transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-methoxy-transdecahydro Naphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-pentyne 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2-vinyl-trans Decahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- ( 3-
(Butenyl) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-pentyl-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene

6- (6-hexyl-tetrahydronaphthalene-2)
-Yl) -2-hexyl-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl)- 2-methoxy-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-propyloxy -Transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-pentyloxy-transdeca Hydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl ) -2-vinyl-transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalene-2 -Il) -2- (3-
(Butenyl) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-hexyl-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-heptyl-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2 -Methoxy-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-propyloxy- Trans-decahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-pentyloxy-transdecahydro Naphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalene-2 -Yl) -2-vinyl-transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalene -2-yl) -2- (3-
(Butenyl) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-heptyl-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene

6- (6-methoxy-tetrahydronaphthalene-2)
-Yl) -2-methoxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl)- 2-propyloxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2-pentyl Oxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2-vinyl-trans Decahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaph Ren-2-yl) -2- (3-
(Butenyl) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-methoxy-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2-ethoxy-transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2 -Propyloxy-transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2-butyloxy-transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2-pentyloxy -Transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2-vinyl-transdeca Hydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydro Naphthalen-2-yl) -2- (3-
(Butenyl) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2- (2-
Propenyloxy) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl ) -2- (2-
(Fluoroethenyl) -transdecahydronaphthalene 6- (6-ethoxy-tetrahydronaphthalen-2-yl) -2- (2,
2-difluoroethenyl) -transdecahydronaphthalene

6- (6-propyloxy-tetrahydronaphthalen-2-yl) -2-propyloxy-transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2-butyloxy-transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2-pentyloxy-transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2-hexyloxy-transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2-vinyl-transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (3-butenyl) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-propyloxy-tetrahydronaphthalen-2-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-Butyloxy-transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-Pentyloxy-transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-Hexyloxy-transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-Vinyl-transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(Trans-1-propenyl) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(3-butenyl) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(Trans-3-pentenyl) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(2-propenyloxy) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(Trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(2-fluoroethenyl) -transdecahydronaphthalene 6- (6-butyloxy-tetrahydronaphthalen-2-yl) -2
-(2,2-difluoroethenyl) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2-pentyloxy-transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2-hexyloxy-transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2-vinyl-transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (3-butenyl) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-pentyloxy-tetrahydronaphthalen-2-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (6-hexyloxy-tetrahydronaphthalen-2-yl) -2-hexyloxy-transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2-vinyl-transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2- (3-butenyl) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
-2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-hexyloxy-tetrahydronaphthalen-2-yl)
-2- (2,2-difluoroethenyl) -transdecahydronaphthalene

6- (6-vinyl-tetrahydronaphthalene-2-
Yl) -2-vinyl-transdecahydronaphthalene 6- (6-vinyl-tetrahydronaphthalen-2-yl) -2- (trans-1-propenyl) -transdecahydronaphthalene 6- (6-vinyl-tetrahydronaphthalene- 2-yl) -2- (3-butenyl) -transdecahydronaphthalene 6- (6-vinyl-tetrahydronaphthalen-2-yl) -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- (6 -Vinyl-tetrahydronaphthalen-2-yl) -2- (2-propenyloxy) -transdecahydronaphthalene 6- (6-vinyl-tetrahydronaphthalen-2-yl) -2- (trans-2-butenyloxy) -trans Decahydronaphthalene 6- (6-vinyl-tetrahydronaphthalen-2-yl) -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- (6-vinyl-tetrahydronaphthalen-2-yl) -2- ( 2,2-
Difluoroethenyl) -transdecahydronaphthalene 6- [6- (trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (trans-1-propenyl) -transdecahydronaphthalene 6- [6- ( Trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (3-butenyl) -transdecahydronaphthalene 6- [6- (trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (Trans-3-pentenyl) -transdecahydronaphthalene 6- [6- (trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (2-propenyloxy) -transdecahydronaphthalene 6- [6 -(Trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- [6- (trans-1-propenyl) -tetrahydronaphthalen-2-yl ] -2- (2-Fluorethenyl) -transdecahydro Phthalene 6- [6- (trans-1-propenyl) -tetrahydronaphthalen-2-yl] -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydro Naphthalen-2-yl] -2
-(3-Butenyl) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydronaphthalen-2-yl] -2
-(Trans-3-pentenyl) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydronaphthalen-2-yl] -2
-(2-propenyloxy) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydronaphthalen-2-yl] -2
-(Trans-2-butenyloxy) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydronaphthalen-2-yl] -2
-(2-Fluoroethenyl) -transdecahydronaphthalene 6- [6- (3-butenyl) -tetrahydronaphthalen-2-yl] -2
-(2,2-difluoroethenyl) -transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -tetrahydronaphthalen-2-yl] -2- (trans-3-pentenyl) -transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -tetrahydronaphthalen-2-yl] -2- (2-propenyloxy) -transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -tetrahydronaphthalene- 2-yl] -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -tetrahydronaphthalen-2-yl] -2- (2-fluoroethenyl)- Transdecahydronaphthalene 6- [6- (trans-3-pentenyl) -tetrahydronaphthalen-2-yl] -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- [6- (2-propenyl) (Oxy) -tetrahydronaphthalene-2
-Yl] -2- (2-propenyloxy) -transdecahydronaphthalene 6- [6- (2-propenyloxy) -tetrahydronaphthalene-2
-Yl] -2- (trans-2-butenyloxy) -transdecahydronaphthalene 6- [6- (2-propenyloxy) -tetrahydronaphthalene-2
-Yl] -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- [6- (2-propenyloxy) -tetrahydronaphthalene-2
-Yl] -2- (2,2-difluoroethenyl) -transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -tetrahydronaphthalen-2-yl] -2- (trans-2-butenyloxy) -Transdecahydronaphthalene 6- [6- (trans-2-butenyloxy) -tetrahydronaphthalen-2-yl] -2- (2-fluoroethenyl) -transdecahydronaphthalene 6- [6- (trans-2- Butenyloxy) -tetrahydronaphthalen-2-yl] -2- (2,2-difluoroethenyl) -transdecahydronaphthalene

Example 8 Preparation of Liquid Crystal Composition (1) General-purpose n-type host liquid crystal composition (H)

[0388]

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Was prepared. This (H) shows a nematic phase at 72.5 ° C. or less, and its melting point is 17 ° C. The physical properties of this composition were as follows.

Dielectric anisotropy (Δε) -1.3 Refractive index anisotropy (Δn) 0.085 Next, 80% by weight of (H) and the compound (I-2) of the present invention obtained in Example 2

[0391]

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A liquid crystal composition (H-2) consisting of 20% by weight was prepared. Liquid crystal (nematic) phase maximum temperature (T _NI ) of this composition
Was 67.1 ° C., and the decrease with respect to (H) could be suppressed to 4 ° C. This (H-5) was allowed to stand at −20 ° C. for 2 weeks, but no precipitation of crystals or phase separation was observed. It was cooled to -60 ° C and crystallized, and its melting point (T _CN ) was measured.
Met. This indicates that the compound (I-2) is also excellent in compatibility with general-purpose liquid crystals.

Next, this (H-2) was filled in a TN cell having a cell thickness of 8.0 μm to prepare a liquid crystal element, and its electro-optical characteristics were measured at 20 ° C .. The results were as follows.

Threshold voltage (Vth) 1.56 V Response time (τ) 43.0 ms Dielectric anisotropy (Δε) 4.2 Refractive index anisotropy (Δn) 0.082 Electric field response because host liquid crystal (H) is n-type Not, but (H
In -2), the dielectric anisotropy (Δ
ε) increased to 4.2, the threshold voltage became 1.56V, and low-voltage driving became possible, and a high-speed response of 43.0 ms was also possible. (Comparative Example 1) In Example 8, a phenyldecahydronaphthalene derivative (R-2) having a similar structure in place of (I-2) but having R as an alkyl group

[0395]

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Was added to (H) in the same amount (20% by weight) to prepare a nematic liquid crystal composition (H-R2). A liquid crystal element was prepared in the same manner, and its electro-optical characteristics were measured. The results were as follows.

Nematic phase maximum temperature (T _NI ) 65.3 ° C. Melting point (T _CN ) 2.0 ° C. Threshold voltage (Vth) 1.68 V Response time (τ) 41.5 ms Dielectric anisotropy (Δε) 4.0 Refractive index anisotropy ( (N) 0.084 (H-R2) has slightly improved response time than (H-2), but T _NI is slightly lower than (H-2) and Vth is about 10% higher than (H-2) .

As described above, the compound (I-2) of the present invention has excellent nematic liquid crystallinity and is very useful for preparing a liquid crystal composition having a greatly reduced threshold voltage. (Example 9) Preparation of liquid crystal composition (2) General-purpose p-type host liquid crystal composition (J)

[0399]

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Was prepared. This (J) shows a nematic phase at 116.7 ° C. or lower, and its melting point is 11.0 ° C. A liquid crystal element was prepared by filling (J) into a TN cell having a cell thickness of 6.0 μm, and the electro-optical characteristics at 20 ° C. were as follows.

Threshold voltage (Vth) 2.14 V Response time (τ) 25.3 ms Steepness (γ) 1.23 Dielectric anisotropy (Δε) 4.8 Refractive index anisotropy (Δn) 0.090 Next, this (J) 80% by weight and the compound (I-1) of the present invention obtained in Example 1.

[0402]

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A liquid crystal composition (J-1) consisting of 20% by weight was prepared. T _NI of the composition was 87.0 ° C.. This (J-1)
Was left at -20 ° C for 4 weeks, but no crystal precipitation or phase separation was observed. In addition, it was cooled down to -60 ° C and left to crystallize, and its _TCN was measured to be 8.0 ° C, which was lower than (J), and (I-1) dissolved well in the host liquid crystal. You can see that it is doing.

Next, a liquid crystal device was prepared by filling (J-1) into a TN cell having a cell thickness of 6.0 μm, and its electro-optical characteristics were measured at 20 ° C., and the results were as follows.

Threshold voltage (Vth) 1.74 V Response time (τ) 44.0 ms Dielectric anisotropy (Δε) 5.8 Refractive index anisotropy (Δn) 0.078 Therefore, by adding 20% of (I-1) The dielectric anisotropy was increased, and the threshold voltage (Vth) was reduced by 0.54V. (Comparative Example 2) In Example 9, instead of (I-1), a phenyldecahydronaphthalene derivative (R-1) having a similar structure but in which R is an alkyl group

[0406]

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The same amount (20% by weight) was added to (J) to prepare a nematic liquid crystal composition (J-R1). A liquid crystal element was prepared in the same manner, and its electro-optical characteristics were measured. The results were as follows.

Nematic phase upper limit temperature (T _NI ) 88.7 ° C. Melting point (T _CN ) 13.0 ° C. Threshold voltage (Vth) 1.69 V Response time (τ) 41.5 ms Dielectric anisotropy (Δε) 5.7 Refractive index anisotropy ( Δn) 0.080 (J-R1) means that Vth is larger than (J-1) and response time is (J-R1).
1) It is slightly improved.

As described above, the compound (I-1) of the present invention is very useful in preparing a liquid crystal composition having excellent nematic liquid crystallinity and compatibility and having a greatly reduced threshold voltage. is there. (Example 10) Preparation of liquid crystal composition (3) 80% by weight of general-purpose p-type host liquid crystal composition (J) and compound of the present invention (I-3) obtained in Example 3

[0410]

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A liquid crystal composition (J-3) consisting of 20% by weight of the above was prepared. T _NI of the composition was 120.3 ° C.. This (J-3)
Was left at -20 ° C for 4 weeks, but no crystal precipitation or phase separation was observed. Also, allowed to stand to crystallize by cooling to -60 ° C., is -10.0 ° C. was measured and the T _CN, can be lowered significantly than (J), (I-3 ) is a host crystal It can be seen that it was dissolved well.

Next, a liquid crystal element was prepared by filling (J-3) into a TN cell having a cell thickness of 6.0 μm, and its electro-optical characteristics were measured at 20 ° C., and the results were as follows.

Threshold voltage (Vth) 2.59 V Response time (τ) 34.8 ms Dielectric anisotropy (Δε) 3.4 Refractive index anisotropy (Δn) 0.101 Therefore, by adding (I-3) by 20%, In addition, the maximum temperature of the nematic phase (T _NI ) increased by about 4 ° C., and the melting point (T _CN ) decreased significantly to −10 ° C. (Comparative Example 3) In Example 10, having a similar structure in place of (I-3), but a 1,4-cyclohexylene group instead of decahydronaphthalene-2,6-diyl group Cyclohexylnaphthalene derivative (R-3)

[0414]

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Was added to (J) in the same amount (20% by weight) to prepare a nematic liquid crystal composition (J-R3). A liquid crystal element was prepared in the same manner, and its electro-optical characteristics were measured. The results were as follows.

Nematic phase maximum temperature (T _NI ) 104.7 ° C. Melting point (T _CN ) 12.0 ° C. Threshold voltage (Vth) 2.43 V Response time (τ) 28.9 ms Dielectric anisotropy (Δε) 3.2 Refractive index anisotropy ( Δn) 0.102 (J-R3) has a T _NI less than (J-3), the nematic phase temperature range is reduced. Therefore, it can be seen that the solubility of (R-3) in the host liquid crystal is not so excellent as compared with (I-3).

As described above, the compound (I-3) of the present invention is very useful for preparing a liquid crystal composition having an improved nematic phase temperature range. In addition, the general formula (I-3)
The compound has no strong polar group in the molecule, can easily obtain a large specific resistance and a high voltage holding ratio, and can be used as a component of a liquid crystal material for driving an active matrix. (Example 11) Preparation of liquid crystal composition (4) 80% by weight of general-purpose p-type host liquid crystal composition (J) and compound of the present invention (I-4) obtained in Example 4

[0418]

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A liquid crystal composition (J-4) consisting of 20% by weight was prepared. T _NI of the composition was 105.7 ° C.. This (J-4)
Was left at -20 ° C for 4 weeks, but no crystal precipitation or phase separation was observed. After cooling to −60 ° C. and allowing it to crystallize, its _TCN was measured to be + 14.2 ° C., which was almost the same as (J), and (I-4) dissolved well in the host liquid crystal. You can see that it is.

Next, a liquid crystal device was prepared by filling (J-4) into a TN cell having a cell thickness of 6.0 μm, and its electro-optical characteristics were measured at 20 ° C., and the results were as follows.

Threshold voltage (Vth) 2.10 V Response time (τ) 33.5 ms Dielectric anisotropy (Δε) 3.8 Refractive index anisotropy (Δn) 0.090 The voltage holding ratio of this device at room temperature and 80 ° C. Measurements revealed that each of them was extremely good and could be used sufficiently for driving an active matrix. (Comparative Example 4) In Example 11, having a similar structure in place of (I-4), but replacing with a decahydronaphthalene-2,6-diyl group with 1,1′-bicyclohexane-4,4 Bicyclohexylnaphthalene derivative which is a '-diyl group (R-4)

[0422]

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The same amount (20% by weight) was added to (J) to prepare a nematic liquid crystal composition (J-R4). A liquid crystal element was prepared in the same manner, and its electro-optical characteristics were measured. The results were as follows.

Nematic phase maximum temperature (T _NI ) 139.2 ° C. Melting point (T _CN ) 33.0 ° C. Threshold voltage (Vth) 2.34 V Response time (τ) 31.7 ms Dielectric anisotropy (Δε) 4.7 Refractive index anisotropy ( Δn) 0.100 (J-R4) is higher than the _{T NI (J-4),} T CN is considerably increased. Therefore, it can be seen that the solubility of (R-4) in the host liquid crystal is not so excellent as compared with (I-4). Further, it can be seen that the electro-optical characteristics of (R-4) are almost the same as (H-4).

As described above, the compound (I-4) of the present invention is very useful for preparing a liquid crystal composition having an improved nematic phase temperature range. In addition, the general formula (I-4)
The compound has no strong polar group in the molecule, can easily obtain a large specific resistance and a high voltage holding ratio, and can be used as a component of a liquid crystal material for driving an active matrix. Example 12 Preparation of Liquid Crystal Composition (5) 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 trans-4-pentylcyclohexanecarboxylic acid 4-methylphenyl 3% by weight of trans-4-propylcyclohexanecarboxylic acid 4-ethoxyphenyl 3% by weight of trans-4- (4-methylphenyl) -trans-4'-
Vinyl bicyclohexane 3% by weight of trans-4-butyl-trans-4'-propylbicyclohexane 4% by weight of trans-4-pentyl-trans-4'-vinylbicyclohexane 3% by weight of 4,4'-bis ( 3-butenyl) bicyclohexane 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'-
Ethyl biphenyl 3% by weight 4- (trans-4-propylcyclohexyl) -1-cyanobenzene 4% by weight 4- [trans-4- (trans-1-propenyl) cyclohexyl] -1-cyanobenzene 3% by weight 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 3,4-difluorophenyl trans-4-pentylcyclohexanecarboxylate 4% by weight 3-fluoro-4-cyanophenyl 4-butylbenzoate 3% by weight of 4- (trans-3-penten-1-yl) benzoic acid Acid 3,5-
Difluoro-4-cyanophenyl 3% by weight of trans-4- (3-fluoro-4-cyanophenyl)-
Trans-4 '-(3-methoxypropyl) bicyclohexane 3% by weight of trans-4- (3,4-difluorophenyl) -trans-4'-ethylbicyclohexane 4% by weight of trans-4- (3,4 -Difluorophenyl) -trans-4'-vinylbicyclohexane 4% by weight of trans-4- (3,4,5-trifluorophenyl) -trans-4'-propylbicyclohexane 3% by weight of trans-4- [ 2- (3,4,5-trifluorophenyl)
Ethyl] -trans-4'-propylbicyclohexane 3% by weight of 4- (trans-4-propylcyclohexyl) -4'-
4% by weight of cyanobiphenyl 4- (trans-4-propylcyclohexyl) 3-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) ethynyl-4-
T _NI of (trans-4-propyl-cyclohexyl) benzene This (M) is 75.0 ° C., [Delta] n was 0.142.
90% of this (M) and obtained in Example 5 (I-1)

[0427]

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3% of (I-2) obtained in Example 1

[0429]

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A liquid crystal composition (MI) consisting of 7% was prepared. T _NI of (MI) is 71.5 ° C., [Delta] n was 0.131.

[0431]

The novel compound of the present invention, a decahydronaphthalene derivative having a ring structure such as a heteroaromatic ring or a condensed aromatic ring, is now commonly used as compared with a conventional decahydronaphthalene derivative having a phenylene group. Is excellent in the compatibility with the liquid crystal compound or the composition, and particularly excellent in the nematic liquid crystal property. By adding the compound, the liquid crystal composition which can improve the nematic phase temperature range and can be driven at a low voltage can be obtained. Therefore, a liquid crystal composition containing the same is extremely useful as a practical liquid crystal, particularly for a liquid crystal display which needs a liquid crystal display material which has a wide nematic liquid crystal temperature range and can be driven at a low voltage.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme court ゛ (Reference) G02F 1/13 500 G02F 1/13 500 (72) Inventor Haruyoshi Takatsu 3-6 Nakahara, Higashiyamato-shi, Tokyo 27 (72) Inventor Gerwald Grahe Berlin, Germany Reichhal Tostrasse 13 14195 (72) Inventor Rainer Bruno Frings, Germany Berlin Petcusser Strasse 16A 12307 (72) Inventor Christine Fugel, Germany Berlin Monumentenstrasse 11 10829 (72) Inventor Cornelia Pitthardt Germany Hirschhorner Beck 28 14163 F-term (reference) 4H006 AA01 AB64 BJ30 BJ50 BM10 BM30 BM71 BM72 BM73 BM74 BN20 BP20 BP30 BS20 GP02 GP03 GP11 GP20 GP22 4H027 BA01 BB03 BB04 BC04 BC05 BD02 BD03 BD04 BD05 BD07 BD08 BD09 BD24 CB01 CB02 CC04 CD04 CL01 CL04 CM01 CM04 CN04 CP01 CP04 CQ01 CQ04 CS04 CT02 CT04 DM04 DM04 DM04 DM04 DM04 DM04 DM04 DM04 DM04 DM04 DM04

Claims (8)

[Claims] 1. A compound of the general formula (I) (In the formula, R represents an alkyl group having 1 to 12 carbon atoms, an alkoxyl group, an alkenyl group, an alkenyloxy group, an alkanoyloxy group or an alkoxycarbonyl group or a cyano group, a cyanato group, a hydroxyl group or a carboxyl group, and L represents- CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , -CH ₂ CH (CH ₃ )-, -CH ₂ O
-, -OCH _2- , -CF ₂ O-, -OCF _2- , -COO-, -OCO-, -CH = CH-,
-CF = CF-, -C≡C-, -O (CH ₂ ) ₃ -,-(CH ₂ ) ₃ O-,-(CH ₂ ) ₄ -or a single bond; Z represents a hydrogen atom or fluorine, Chlorine, bromine or iodine halogen atom or alkyl group having 1 to 12 carbon atoms, alkoxyl group, alkenyl group, alkenyloxy group, alkanoyloxy group or alkoxycarbonyl group or cyano group, cyanato group, hydroxyl group or carboxyl group, Ring Q is 1,4-phenylene group, pyrimidine-2,5-diyl group, pyridine-2,5-
Diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group, bicyclo [2.2.2] octane-1,4-diyl group , Naphthalene-2,6-
Diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group, the decahydronaphthalene ring is in trans form,
The 2,6-position is in the trans configuration, but when R or Z represents an alkyl group, an alkoxyl group, an alkenyl group, an alkenyloxy group, an alkanoyloxy group or an alkoxycarbonyl group, each has one or more fluorine atoms or carbon atoms. May be substituted by 1 to 7 alkoxyl groups, ring Q may be substituted by one or more fluorine atoms, provided that when ring Q represents a 1,4-phenylene group, R represents an alkoxyl group or an alkenyl group; L represents a oxy group, L represents a single bond, and ring Q is at least one substituted by a fluorine atom, and ring Q is decahydronaphthalene-2,6-
When R represents an alkyl group and Z represents an alkanoyloxy group, L is not a single bond or -COO-, and ring Q represents a decahydronaphthalene-2,6-diyl group and R and When Z both represent an alkoxyl group or an alkanoyloxy group, L is not a single bond, and ring Q represents a naphthalene-2,6-diyl group and R represents an unsubstituted alkyl group or an unsubstituted alkoxyl group. And when L represents -COO-, the ring Q represents a compound substituted by at least one fluorine atom. A) a decahydronaphthalene derivative represented by the formula: 2. In the general formula (I), L is -CH ₂ CH _2- , -CH ₂ O
_{-, - OCH 2 -, -} CF 2 O -, - OCF 2 -, - COO -, - OCO -, - CF = CF- or decahydronaphthalene derivative according to claim 1, wherein where represents a single bond. 3. In the general formula (I), the ring Q is 1,4-phenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydro Naphthalene-
2. The decahydronaphthalene derivative according to claim 1, which represents a 2,6-diyl group. 4. In the general formula (I), R is an alkyl group having 1 to 12 carbon atoms, an alkoxyl group, an alkenyl group which may be substituted by one or more fluorine atoms or an alkoxyl group having 1 to 7 carbon atoms. 2. The decahydronaphthalene derivative according to claim 1, which represents a group or an alkenyloxy group. 5. In the formula (I), Z is substituted by a hydrogen atom, a halogen atom of fluorine, chlorine, bromine or iodine, or one or more fluorine atoms or an alkoxyl group having 1 to 7 carbon atoms. Good carbon atoms 1
2. The decahydronaphthalene derivative according to claim 1, which represents an alkyl group, an alkoxyl group, an alkenyl group, an alkenyloxy group or a cyano group. 6. The decahydronaphthalene derivative according to claim 1, wherein L in formula (I) represents a single bond. 7. A liquid crystal composition comprising the compound represented by the general formula (I) according to claim 1. 8. A liquid crystal device comprising the liquid crystal composition according to claim 7 as a constituent element.