JPS58134046A - トランス−４−アルキルオキシメチル−１−（４′−アルキルビフエニリル−４）シクロヘキサン類 - Google Patents
トランス−４−アルキルオキシメチル−１−（４′−アルキルビフエニリル−４）シクロヘキサン類Info
- Publication number
- JPS58134046A JPS58134046A JP1588682A JP1588682A JPS58134046A JP S58134046 A JPS58134046 A JP S58134046A JP 1588682 A JP1588682 A JP 1588682A JP 1588682 A JP1588682 A JP 1588682A JP S58134046 A JPS58134046 A JP S58134046A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- trans
- reacted
- liquid crystal
- formula
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- SRPSOCQMBCNWFR-UHFFFAOYSA-N iodous acid Chemical compound OI=O SRPSOCQMBCNWFR-UHFFFAOYSA-N 0.000 abstract 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 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 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- -1 lithium aluminum hydride Chemical compound 0.000 description 4
- CKUNTDNDGXPOPB-UHFFFAOYSA-N 4-butylcyclohexan-1-one Chemical compound CCCCC1CCC(=O)CC1 CKUNTDNDGXPOPB-UHFFFAOYSA-N 0.000 description 3
- NQEDLIZOPMNZMC-UHFFFAOYSA-N 4-propylcyclohexan-1-one Chemical compound CCCC1CCC(=O)CC1 NQEDLIZOPMNZMC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SRPDEHMURXAMGW-UHFFFAOYSA-N (4-phenylcyclohexyl)methanol Chemical compound C1CC(CO)CCC1C1=CC=CC=C1 SRPDEHMURXAMGW-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- OKSDJGWHKXFVME-UHFFFAOYSA-N 4-ethylcyclohexan-1-one Chemical compound CCC1CCC(=O)CC1 OKSDJGWHKXFVME-UHFFFAOYSA-N 0.000 description 1
- QQBCXOPRVOCINO-UHFFFAOYSA-N 4-hexylcyclohexan-1-one Chemical compound CCCCCCC1CCC(=O)CC1 QQBCXOPRVOCINO-UHFFFAOYSA-N 0.000 description 1
- UKLNPJDLSPMJMQ-UHFFFAOYSA-N 4-pentylcyclohexan-1-one Chemical compound CCCCCC1CCC(=O)CC1 UKLNPJDLSPMJMQ-UHFFFAOYSA-N 0.000 description 1
- XUPTVKORAROJNP-UHFFFAOYSA-N C(CCCCC)OCCCCCC.[Na] Chemical compound C(CCCCC)OCCCCCC.[Na] XUPTVKORAROJNP-UHFFFAOYSA-N 0.000 description 1
- AXBYOBGLQCWUGP-UHFFFAOYSA-N C(CCCCCCC)OCCCCCCCC.[Na] Chemical compound C(CCCCCCC)OCCCCCCCC.[Na] AXBYOBGLQCWUGP-UHFFFAOYSA-N 0.000 description 1
- SRPDEHMURXAMGW-AULYBMBSSA-N C1(=CC=CC=C1)[C@@H]1CC[C@H](CC1)CO Chemical compound C1(=CC=CC=C1)[C@@H]1CC[C@H](CC1)CO SRPDEHMURXAMGW-AULYBMBSSA-N 0.000 description 1
- GKKYLFIDGREUAD-UHFFFAOYSA-N CC1CCC(CC1)=O.CC1CCC(CC1)=O Chemical compound CC1CCC(CC1)=O.CC1CCC(CC1)=O GKKYLFIDGREUAD-UHFFFAOYSA-N 0.000 description 1
- XQCYLFPNPVBVNG-LSAOGOSGSA-N COC[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C)C1=CCCCC1 Chemical compound COC[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C)C1=CCCCC1 XQCYLFPNPVBVNG-LSAOGOSGSA-N 0.000 description 1
- 101000796022 Homo sapiens Thioredoxin-interacting protein Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 102100031344 Thioredoxin-interacting protein Human genes 0.000 description 1
- NMRUTZHKRXABQM-UHFFFAOYSA-N [4-(methoxymethyl)cyclohexyl]benzene Chemical compound C1CC(COC)CCC1C1=CC=CC=C1 NMRUTZHKRXABQM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MCYYJHPHBOPLMH-UHFFFAOYSA-L disodium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane;hydrate Chemical compound O.[Na+].[Na+].[O-]S([O-])(=O)=S MCYYJHPHBOPLMH-UHFFFAOYSA-L 0.000 description 1
- QCUPYFTWJOZAOB-HYXAFXHYSA-N ectylurea Chemical compound CC\C(=C\C)C(=O)NC(N)=O QCUPYFTWJOZAOB-HYXAFXHYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 229930183328 quinanone Natural products 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102220092092 rs876657864 Human genes 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1588682A JPS58134046A (ja) | 1982-02-03 | 1982-02-03 | トランス−４−アルキルオキシメチル−１−（４′−アルキルビフエニリル−４）シクロヘキサン類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1588682A JPS58134046A (ja) | 1982-02-03 | 1982-02-03 | トランス−４−アルキルオキシメチル−１−（４′−アルキルビフエニリル−４）シクロヘキサン類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58134046A true JPS58134046A (ja) | 1983-08-10 |
| JPH0316330B2 JPH0316330B2 (en]) | 1991-03-05 |
Family
ID=11901269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1588682A Granted JPS58134046A (ja) | 1982-02-03 | 1982-02-03 | トランス−４−アルキルオキシメチル−１−（４′−アルキルビフエニリル−４）シクロヘキサン類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58134046A (en]) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507222A (en) * | 1982-03-26 | 1985-03-26 | Chisso Corporation | Liquid-crystalline compounds |
| US4522741A (en) * | 1982-06-12 | 1985-06-11 | Chisso Corporation | Trans-4-alkyloxymethyl-1-(4'-substituted biphenylyl-4)cyclohexanes |
| US4564694A (en) * | 1981-02-25 | 1986-01-14 | Hitachi, Ltd. | Colorless liquid crystalline compounds |
| EP0857774A3 (en) * | 1997-02-10 | 1998-09-02 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57140737A (en) * | 1981-02-25 | 1982-08-31 | Kanto Kagaku Kk | Colorless liquid crystal substance, colorless liquid crystal composition, and display element of liquid crystal |
-
1982
- 1982-02-03 JP JP1588682A patent/JPS58134046A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57140737A (en) * | 1981-02-25 | 1982-08-31 | Kanto Kagaku Kk | Colorless liquid crystal substance, colorless liquid crystal composition, and display element of liquid crystal |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4564694A (en) * | 1981-02-25 | 1986-01-14 | Hitachi, Ltd. | Colorless liquid crystalline compounds |
| US4694098A (en) * | 1981-02-25 | 1987-09-15 | Hitachi, Ltd. | Colorless liquid crystalline compounds |
| US4507222A (en) * | 1982-03-26 | 1985-03-26 | Chisso Corporation | Liquid-crystalline compounds |
| US4704228A (en) * | 1982-03-26 | 1987-11-03 | Chisso Corporation | Liquid-crystalline compounds |
| US4522741A (en) * | 1982-06-12 | 1985-06-11 | Chisso Corporation | Trans-4-alkyloxymethyl-1-(4'-substituted biphenylyl-4)cyclohexanes |
| US4617141A (en) * | 1982-06-12 | 1986-10-14 | Chisso Corporation | Trans-4-alkyloxymethyl-1-(4'-substituted biphenylyl-4)cyclohexanes |
| EP0857774A3 (en) * | 1997-02-10 | 1998-09-02 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0316330B2 (en]) | 1991-03-05 |
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