# US 5,707,547 A · Trans-olefin compounds, method for production thereof, liquid crystal composition containing the same as active ingredient, and liquid crystal element using said composition

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- Number: US 5,707,547 A
- Document ID: US5707547A
- Status: Granted
- Kind: A
- Application number: 08/282,024
- Filed: 1994-07-29
- Granted: 1998-01-13
- Earliest claimed: 1993-08-03
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Yukari Fujimoto; Naoyuki Takano; Takayuki Higashii; Masayoshi Minai; Chizu Sekine; Kayoko Ueda; Koichi Fujisawa; Kyoko Endo; Takeshi Tani
- Web page: https://patentgrep.com/patent/US5707547A

## CPC

- C07D 213/30: Oxygen atoms
- C07C 43/215: having unsaturation outside the six-membered aromatic rings
- C07C 43/225: containing halogen
- C07C 69/007: Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
- C07D 213/64: attached in position 2 or 6
- C07D 215/14: Radicals substituted by oxygen atoms
- C07D 237/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 239/34: One oxygen atom
- C07D 241/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C09K 19/04: characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit}
- C09K 19/12: at least two benzene rings directly linked, e.g. biphenyls
- C09K 19/126: {Compounds containing at least one asymmetric carbon atom}
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/3441: {having nitrogen as hetero atom}
- C09K 19/3444: {the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine}
- C09K 19/3452: {Pyrazine}
- C09K 19/3455: {Pyridazine}
- C09K 19/3463: {Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines}
- C09K 19/3466: {Pyrimidine with at least another heterocycle in the chain}
- C09K 19/3469: {Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-}
- C09K 19/46: containing esters
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to trans-olefin compounds represented by the general formula (1) useful as an ingredient of liquid crystal composition, trans-olefin compounds useful as intermediate of pesticides, medical drugs, liquid crystal materials and the like, a process for producing those trans-olefin compounds, a liquid crystal composition containing the trans-olefin compound as an active ingredient, and a liquid crystal element using the liquid crystal composition. ##STR1## (In the general formula (1), R.sup.1, A.sup.1, A.sup.2, A.sup.3, Z and R.sup.2 are same as defined in the specification. Also, m, p, q, n, r, s and t are each an integer as defined in the specification.)

## Claims

### Claim 1

An optically active trans-olefin compound represented by general formula (1): ##STR761## wherein n is an integer of 0-10; m, r, s and t each represents 0 or 1; Z is hydrogen atom or fluorine atom; R.sup.1 is hydrogen, saturated or unsaturated alkyl group having 1-20 carbon atoms, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms, provided that when m=1, R.sup.1 may also be a protecting group as hereinafter defined and when r=0, s=0 and t=0, R.sup.1 cannot be an unsaturated alkyl group; R.sup.2 is hydrogen atom, saturated or unsaturated alkyl group having 1-20 carbon atoms optionally substituted by halogen atom, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms optionally substituted by halogen atom, provided that when s=1 and t=0, R.sup.2 may also be a protecting group as hereinafter defined, wherein the protecting group of R.sup.1 and R.sup.2, which may be the same or different, is selected from the group consisting of aliphatic acyl group which may optionally be substituted by halogen atom or by alkoxy group; benzoyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; benzyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; trialkylsilyl group, dialkylphenylsilyl group, alkyldiphenylsilyl group, triphenylsilyl group, aralkyldialkylsilyl group, diaralkylalkylsilyl group and triaralkylsilyl group, provided that the phenyl and aralkyl groups in the above-mentioned groups may optionally be substituted by halogen atom, alkyl group, alkoxy group; and tetrahydropyranyl group, tetrahydrofuranyl group and 1-(alkoxy)-alkyl groups, which may optionally be substituted by halogen atom or alkoxy group; A.sup.1, A.sup.2 and A.sup.3 each represents one of the following groups: ##STR762## in which i is an integer of 0-4; j and k are each an integer of 0-3; and p and q are 0 or 1, provided that when A.sup.1 is a fused ring, p+q=0 or 1 and A.sup.2 and A.sup.3 are single rings, and when A.sup.1 is a single ring, p+q=1 or 2, provided that when p+q=2, A.sup.2 and A.sup.3 are both single rings provided that at least one of A.sup.1, A.sup.2 and A.sup.3 is a group of ##STR763## wherein i is an integer of 1-4, or a group of ##STR764## wherein J is an integer of 1-3 or k is an integer of 1-3.

### Claim 2

A liquid crystal composition containing at least one transolefin compound represented by general formula (1): ##STR765## wherein n is an integer of 0-10; m, r, s and t each represents 0 or 1; Z is hydrogen atom or fluorine atom; R.sup.1 is hydrogen, saturated or unsaturated alkyl group having 1-20 carbon atoms, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms, provided that when m=1, R.sup.1 may also be a protecting group as hereinafter defined and when r=0, s=0 and t=0, R.sup.1 cannot be an unsaturated alkyl group; R.sup.2 is hydrogen atom, saturated or unsaturated alkyl group having 1-20 carbon atoms optionally substituted by halogen atom, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms optionally substituted by halogen atom, provided that when s=1 and t=0, R.sup.2 may also be a protecting group as hereinafter defined, wherein the protecting group of R.sup.1 and R.sup.2, which may be the same or different, is selected from the group consisting of aliphatic acyl group which may optionally be substituted by halogen atom or by alkoxy group; benzoyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; benzyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; trialkylsilyl group, dialkylphenylsilyl group, alkyldiphenylsilyl group, triphenylsilyl group, aralkyldialkylsilyl group, diaralkylalkylsilyl group and triaralkylsilyl group, provided that the phenyl and aralkyl groups in the above-mentioned groups may optionally be substituted by halogen atom, alkyl group, alkoxy group; and tetrahydropyranyl group, tetrahydrofuranyl group and 1-(alkoxy)-alkyl groups, which may optionally be substituted by halogen atom or alkoxy group; A.sup.1, A.sup.2, and A.sup.3 each represents one of the following groups: ##STR766## in which i is an integer of 0-4; j and k are each an integer of 0-3; and p and q are 0 or 1, provided that when A.sup.1 is a fused ring, p+q=0 or 1 and A.sup.2 and A.sup.3 are single rings, and when A.sup.1 is a single ring, p+q=1 or 2, provided that when p+q=2, A.sup.2 and A.sup.3 are both single rings provided that at least one of A.sup.1, A.sup.2 and A.sup.3 is a group of ##STR767## wherein i is an integer of 1-4, or a group of ##STR768## wherein J is an integer of 1-3 or k is an integer of 1-3, and at least one trans-olefin compound represented by the general formula (1'): ##STR769## wherein n is an integer of 0-10; m, r, s and t each represent 0 or 1; Z is hydrogen atom or fluorine atom; R.sup.1 is hydrogen, saturated or unsaturated alkyl group having 1-20 carbon atoms, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms, provided that when m=1, R.sup.1 may also be a protecting group as hereinafter defined and when r=0, s=0 and t=0, R.sup.1 cannot be unsaturated alkyl group; R.sup.2 is hydrogen atom, saturated or unsaturated alkyl group having 1-20 carbon atoms optionally substituted by halogen atom, or saturated or unsaturated alkoxyalkyl group having 2-20 carbon atoms optionally substituted by halogen atom, provided that when s=1 and t=0, R.sup.2 may also be a protecting group as hereinafter defined, wherein the protecting group of R.sup.1 and R.sup.2, which may be the same or different, is selected from the group consisting of aliphatic acyl group which may optionally be substituted by halogen atom or by alkoxy group; benzoyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; benzyl group which may optionally be substituted by halogen atom, or by alkyl group, or by alkoxy group, or by nitro group, or by cyano group; trialkylsilyl group, dialkylphenylsilyl group, alkyldiphenylsilyl group, triphenylsilyl group, aralkyldialkylsilyl group, diaralkylalkylsilyl group and triaralkylsilyl group, provided that the phenyl and aralkyl groups in the above-mentioned groups may optionally be substituted by halogen atom, alkyl group, alkoxy group; and tetrahydropyranyl group, tetrahydrofuranyl group and 1-(alkoxy)-alkyl groups, which may optionally be substituted by halogen atom or alkoxy group; A.sup.1, A.sup.2 and A.sup.3 each represents one of the following groups: ##STR770## in which i, j and k each represents 0; and p and q are 0 or 1, provided that when A.sup.1 is a fused ring, p+q=0 or 1 and A.sup.2 and A.sup.3 are single rings, and when A.sup.1 is a single ring, p+q=1 or 2, provided that when p+q=2, A.sup.2 and A.sup.3 are both single rings wherein the rings A.sup.1, A.sup.2 and A.sup.3 have no fluorine atom.

### Claim 3 (depends on 2)

A liquid crystal composition according to claim 2 which further comprises an optically active compound.