JPS6092276A - ピラジン誘導体 - Google Patents

Info

Publication number

JPS6092276A

JPS6092276A JP20142983A JP20142983A JPS6092276A JP S6092276 A JPS6092276 A JP S6092276A JP 20142983 A JP20142983 A JP 20142983A JP 20142983 A JP20142983 A JP 20142983A JP S6092276 A JPS6092276 A JP S6092276A

Authority

JP

Japan

Prior art keywords

formula

compound

liquid crystal

phase

optically active

Prior art date

1983-10-27

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

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• 150000003216 pyrazines Chemical class 0.000 title claims 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 42
• 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 27
• 239000004990 Smectic liquid crystal Substances 0.000 claims abstract description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
• 230000001747 exhibiting effect Effects 0.000 claims abstract description 5
• 230000003287 optical effect Effects 0.000 claims abstract description 4
• 239000000203 mixture Substances 0.000 claims description 20
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract description 10
• 239000000126 substance Substances 0.000 abstract description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 5
• WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 abstract description 3
• 239000013078 crystal Substances 0.000 abstract description 3
• 230000015572 biosynthetic process Effects 0.000 abstract description 2
• 150000001350 alkyl halides Chemical class 0.000 abstract 1
• 239000000463 material Substances 0.000 abstract 1
• 230000001590 oxidative effect Effects 0.000 abstract 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
• 239000012071 phase Substances 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
• 238000000034 method Methods 0.000 description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 230000007704 transition Effects 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 230000004044 response Effects 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 239000007788 liquid Substances 0.000 description 5
• 230000010287 polarization Effects 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
• NEKGDYGTJYCIRI-UHFFFAOYSA-N 4-octylbenzoyl chloride Chemical compound CCCCCCCCC1=CC=C(C(Cl)=O)C=C1 NEKGDYGTJYCIRI-UHFFFAOYSA-N 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 239000004988 Nematic liquid crystal Substances 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-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
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
• 239000004372 Polyvinyl alcohol Substances 0.000 description 3
• 230000003098 cholesteric effect Effects 0.000 description 3
• 229920002451 polyvinyl alcohol Polymers 0.000 description 3
• 230000002269 spontaneous effect Effects 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• -1 2-p-octylbenzoyloxy-5 -(2-methylbutyloxyphenyl)pyrazine Chemical compound 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 210000002858 crystal cell Anatomy 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• JYVLIDXNZAXMDK-UHFFFAOYSA-N methyl propyl carbinol Natural products CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 229910052711 selenium Inorganic materials 0.000 description 2
• 239000011669 selenium Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• XKVLZBNEPALHIO-UHFFFAOYSA-N 1-bromo-2-methylbutane Chemical compound CCC(C)CBr XKVLZBNEPALHIO-UHFFFAOYSA-N 0.000 description 1
• QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methyl-1-butanol Substances CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
• DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 1
• IALWCYFULVHLEC-UHFFFAOYSA-N 4-(octyloxy)benzoic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=C1 IALWCYFULVHLEC-UHFFFAOYSA-N 0.000 description 1
• HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 239000001000 anthraquinone dye Substances 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 230000001186 cumulative effect Effects 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000005401 electroluminescence Methods 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000003446 memory effect Effects 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1

Cited By (7)