JPS61215375A - 安息香酸ピリミジニルフエニルエステル誘導体 - Google Patents
安息香酸ピリミジニルフエニルエステル誘導体Info
- Publication number
- JPS61215375A JPS61215375A JP60056655A JP5665585A JPS61215375A JP S61215375 A JPS61215375 A JP S61215375A JP 60056655 A JP60056655 A JP 60056655A JP 5665585 A JP5665585 A JP 5665585A JP S61215375 A JPS61215375 A JP S61215375A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- benzoic acid
- pyrimidinylphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- GDNXXGJBLPEXCW-UHFFFAOYSA-N (2-pyrimidin-2-ylphenyl) benzoate Chemical class N1=C(N=CC=C1)C1=C(C=CC=C1)OC(C1=CC=CC=C1)=O GDNXXGJBLPEXCW-UHFFFAOYSA-N 0.000 title abstract 2
- -1 phenyl ester Chemical class 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 37
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 230000005684 electric field Effects 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 230000005621 ferroelectricity Effects 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000004990 Smectic liquid crystal Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YNPVNLWKVZZBTM-ZETCQYMHSA-N (4s)-4-methylhexan-1-ol Chemical compound CC[C@H](C)CCCO YNPVNLWKVZZBTM-ZETCQYMHSA-N 0.000 description 1
- BJKXZCGJAOWNTN-JTQLQIEISA-N (7s)-7-methylnonan-1-ol Chemical compound CC[C@H](C)CCCCCCO BJKXZCGJAOWNTN-JTQLQIEISA-N 0.000 description 1
- QPRQEDXDYOZYLA-YFKPBYRVSA-N (S)-2-methylbutan-1-ol Chemical compound CC[C@H](C)CO QPRQEDXDYOZYLA-YFKPBYRVSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- PPQAGRXNKROYIP-UHFFFAOYSA-N 1-methyl-2-phenyl-3-propylindole Chemical compound CN1C2=CC=CC=C2C(CCC)=C1C1=CC=CC=C1 PPQAGRXNKROYIP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 1
- PGFNVWGMBZSAEW-ZDUSSCGKSA-N 4-[(6s)-6-methyloctoxy]benzoic acid Chemical compound CC[C@H](C)CCCCCOC1=CC=C(C(O)=O)C=C1 PGFNVWGMBZSAEW-ZDUSSCGKSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- VHVJRSVTZPYXEH-UHFFFAOYSA-N [amino-(4-hydroxyphenyl)methylidene]azanium;chloride Chemical compound Cl.NC(=N)C1=CC=C(O)C=C1 VHVJRSVTZPYXEH-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000005261 decarburization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Chemical group 0.000 description 1
- 239000002184 metal Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60056655A JPS61215375A (ja) | 1985-03-20 | 1985-03-20 | 安息香酸ピリミジニルフエニルエステル誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60056655A JPS61215375A (ja) | 1985-03-20 | 1985-03-20 | 安息香酸ピリミジニルフエニルエステル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61215375A true JPS61215375A (ja) | 1986-09-25 |
| JPH0425952B2 JPH0425952B2 (enrdf_load_stackoverflow) | 1992-05-06 |
Family
ID=13033388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60056655A Granted JPS61215375A (ja) | 1985-03-20 | 1985-03-20 | 安息香酸ピリミジニルフエニルエステル誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61215375A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725688A (en) * | 1984-06-07 | 1988-02-16 | Seiko Instruments Inc. | Liquid crystal compound |
| EP0262809A1 (en) * | 1986-09-02 | 1988-04-06 | Teikoku Chemical Industry Co., Ltd. | Pyrimidinylphenyl ester compound |
| US4826979A (en) * | 1986-06-13 | 1989-05-02 | Alps Electric Co., Ltd. | Liquid crystal compound |
| US4835274A (en) * | 1986-06-13 | 1989-05-30 | Alps Electric Co., Ltd. | Liquid crystal compound |
| US4834904A (en) * | 1985-04-27 | 1989-05-30 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Nitrogen-containing heterocycles |
| US4891151A (en) * | 1987-09-19 | 1990-01-02 | Hoechst Aktiengesellschaft | Liquid-crystalline phenylpyrimidinyl cyclohexanecarboxylates having a smectic phase, a process for their preparation, and their use in liquid-crystal mixtures |
| US5055221A (en) * | 1985-05-24 | 1991-10-08 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Smectic liquid-crystalline phases |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653661A (en) * | 1979-08-20 | 1981-05-13 | Ueruku Fuyuuru Fuerunzeeerekut | Nematic crystal liquid 55alkyll22*44acyloxyy phenyl**pyrimidine* its manufacture and its use |
-
1985
- 1985-03-20 JP JP60056655A patent/JPS61215375A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653661A (en) * | 1979-08-20 | 1981-05-13 | Ueruku Fuyuuru Fuerunzeeerekut | Nematic crystal liquid 55alkyll22*44acyloxyy phenyl**pyrimidine* its manufacture and its use |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725688A (en) * | 1984-06-07 | 1988-02-16 | Seiko Instruments Inc. | Liquid crystal compound |
| US4834904A (en) * | 1985-04-27 | 1989-05-30 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Nitrogen-containing heterocycles |
| US5055221A (en) * | 1985-05-24 | 1991-10-08 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Smectic liquid-crystalline phases |
| US4826979A (en) * | 1986-06-13 | 1989-05-02 | Alps Electric Co., Ltd. | Liquid crystal compound |
| US4835274A (en) * | 1986-06-13 | 1989-05-30 | Alps Electric Co., Ltd. | Liquid crystal compound |
| EP0262809A1 (en) * | 1986-09-02 | 1988-04-06 | Teikoku Chemical Industry Co., Ltd. | Pyrimidinylphenyl ester compound |
| US4891151A (en) * | 1987-09-19 | 1990-01-02 | Hoechst Aktiengesellschaft | Liquid-crystalline phenylpyrimidinyl cyclohexanecarboxylates having a smectic phase, a process for their preparation, and their use in liquid-crystal mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0425952B2 (enrdf_load_stackoverflow) | 1992-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term |