JPS60146877A - ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン - Google Patents
２―置換―６―（５―置換―２―ピリミジニル）ナフタリンInfo
- Publication number
- JPS60146877A JPS60146877A JP59003122A JP312284A JPS60146877A JP S60146877 A JPS60146877 A JP S60146877A JP 59003122 A JP59003122 A JP 59003122A JP 312284 A JP312284 A JP 312284A JP S60146877 A JPS60146877 A JP S60146877A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- substituted
- pyrimidinyl
- compound
- naphthalene
- 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
- -1 2-substituted-6-(5-substituted-2-pyrimidinyl)naphthalene Chemical class 0.000 title abstract description 6
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 abstract description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 2
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 230000007423 decrease Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 210000002858 crystal cell Anatomy 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- PEUUEJUQHBNLCX-UHFFFAOYSA-N 5-butyl-2-(6-pentoxynaphthalen-2-yl)pyrimidine Chemical compound C1=CC2=CC(OCCCCC)=CC=C2C=C1C1=NC=C(CCCC)C=N1 PEUUEJUQHBNLCX-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MKBAQNGVFLNOTL-UHFFFAOYSA-N 2-(6-heptylnaphthalen-2-yl)-5-hexylpyrimidine Chemical compound C1=CC2=CC(CCCCCCC)=CC=C2C=C1C1=NC=C(CCCCCC)C=N1 MKBAQNGVFLNOTL-UHFFFAOYSA-N 0.000 description 1
- BOCLNHHITMVKPJ-UHFFFAOYSA-N 2-(6-pentoxynaphthalen-2-yl)-5-propylpyrimidine Chemical compound C1=CC2=CC(OCCCCC)=CC=C2C=C1C1=NC=C(CCC)C=N1 BOCLNHHITMVKPJ-UHFFFAOYSA-N 0.000 description 1
- ACTFEOAZWWJXLT-UHFFFAOYSA-N 2-naphthalen-1-ylpyrimidine Chemical compound N1=CC=CN=C1C1=CC=CC2=CC=CC=C12 ACTFEOAZWWJXLT-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000005684 electric field Effects 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
- MPOKJOWFCMDRKP-UHFFFAOYSA-N gold;hydrate Chemical compound O.[Au] MPOKJOWFCMDRKP-UHFFFAOYSA-N 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59003122A JPS60146877A (ja) | 1984-01-11 | 1984-01-11 | ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン |
| US06/683,162 US4585575A (en) | 1984-01-11 | 1984-12-18 | 2-substituted-6-(5-substituted-2-pyrimidinyl)naphthalenes |
| EP84115764A EP0151294B1 (en) | 1984-01-11 | 1984-12-19 | 2-substituted-6-(5-substituted-2-pyrimidinyl)naphthalenes and liquid crystal compositions containing the same |
| DE8484115764T DE3472254D1 (en) | 1984-01-11 | 1984-12-19 | 2-substituted-6-(5-substituted-2-pyrimidinyl)naphthalenes and liquid crystal compositions containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59003122A JPS60146877A (ja) | 1984-01-11 | 1984-01-11 | ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60146877A true JPS60146877A (ja) | 1985-08-02 |
| JPH0428265B2 JPH0428265B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-13 |
Family
ID=11548550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59003122A Granted JPS60146877A (ja) | 1984-01-11 | 1984-01-11 | ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン |
Country Status (4)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002146354A (ja) * | 2000-11-08 | 2002-05-22 | Dainippon Ink & Chem Inc | 液晶組成物 |
| JP2017528520A (ja) * | 2014-08-29 | 2017-09-28 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | ハンチントンタンパク質のイメージング用プローブ |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61152659A (ja) * | 1984-12-27 | 1986-07-11 | Chisso Corp | １，４−ジピリミジニルベンゼン誘導体 |
| GB8610349D0 (en) * | 1986-04-28 | 1986-06-04 | Bdh Ltd | 6-hydroxy-2-naphthoic acid derivatives |
| CA1294954C (en) * | 1986-12-26 | 1992-01-28 | Masakatsu Nakatsuka | Optically active naphthalene derivatives |
| US4908458A (en) * | 1988-12-15 | 1990-03-13 | Shell Oil Company | Ketoheterocyclic derivatives |
| US5496500A (en) * | 1991-03-13 | 1996-03-05 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain & Northern Ireland | Naphthyl organic compounds |
| EP0517498A1 (en) * | 1991-06-03 | 1992-12-09 | Sanyo Chemical Industries Ltd. | Liquid crystal compounds and compositions |
| DE4434754A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Ag | Neue Verbindungen zur Verwendung in Flüssigkristallmischungen |
| WO2001077082A1 (fr) * | 1999-06-02 | 2001-10-18 | Torii Pharmaceutical Co., Ltd. | Derives de naphtalene |
| US9271963B2 (en) * | 2005-03-03 | 2016-03-01 | Universitat Des Saarlandes | Selective inhibitors of human corticosteroid synthases |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH617452A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-10-25 | 1980-05-30 | Hoffmann La Roche | |
| US4062798A (en) * | 1975-09-19 | 1977-12-13 | Hoffmann-La Roche Inc. | Phenylpyrimidine derivatives |
| DE2949080A1 (de) * | 1979-12-06 | 1981-06-11 | Merck Patent Gmbh, 6100 Darmstadt | Naphthalinderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| DE2951099A1 (de) * | 1979-12-19 | 1981-06-25 | Merck Patent Gmbh, 6100 Darmstadt | Tetrahydrochinazoline, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement |
| DD160394A3 (de) * | 1980-09-29 | 1983-07-27 | Dietrich Demus | Anwendung fluessig-kristalliner substanzen |
| DE3131593A1 (de) * | 1980-09-29 | 1982-06-24 | VEB Werk für Fernsehelektronik im VEB Kombinat Mikroelektronik, DDR 1160 Berlin | Kristallin-fluessige substanzen |
| CH645664A5 (de) * | 1980-12-16 | 1984-10-15 | Merck Patent Gmbh | Fluessigkristallmischung. |
| DD208167A5 (de) * | 1980-12-23 | 1984-03-28 | Hoffmann La Roche | Decaline |
| DE3270906D1 (en) * | 1982-01-14 | 1986-06-05 | Merck Patent Gmbh | Liquid crystal mixtures |
| JPS5939876A (ja) * | 1982-08-26 | 1984-03-05 | Chisso Corp | ピリミジン誘導体 |
-
1984
- 1984-01-11 JP JP59003122A patent/JPS60146877A/ja active Granted
- 1984-12-18 US US06/683,162 patent/US4585575A/en not_active Expired - Lifetime
- 1984-12-19 EP EP84115764A patent/EP0151294B1/en not_active Expired
- 1984-12-19 DE DE8484115764T patent/DE3472254D1/de not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002146354A (ja) * | 2000-11-08 | 2002-05-22 | Dainippon Ink & Chem Inc | 液晶組成物 |
| JP2017528520A (ja) * | 2014-08-29 | 2017-09-28 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | ハンチントンタンパク質のイメージング用プローブ |
Also Published As
| Publication number | Publication date |
|---|---|
| US4585575A (en) | 1986-04-29 |
| EP0151294A1 (en) | 1985-08-14 |
| DE3472254D1 (en) | 1988-07-28 |
| EP0151294B1 (en) | 1988-06-22 |
| JPH0428265B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60146877A (ja) | ２―置換―６―（５―置換―２―ピリミジニル）ナフタリン | |
| JPS6322568A (ja) | ２−（トランス−４−アルキルシクロヘキシル）−５−アルコキシピリミジン | |
| JPS60255779A (ja) | 複素環化合物 | |
| JPS60193969A (ja) | シクロヘキシルピリミジン誘導体 | |
| JPS61152659A (ja) | １，４−ジピリミジニルベンゼン誘導体 | |
| JPS60132978A (ja) | ２−置換−６−（トランス−５−アルキル−１，３−ジオキサン−２−イル）ナフタレン | |
| JPS58121272A (ja) | ３−クロロ−６−ヒドロキシピリジンのエステル誘導体 | |
| US5366657A (en) | Geminal dimethylalkyl compounds, process for their preparation and their use in liquid-crystalline mixtures | |
| JPS60199878A (ja) | ６−置換−２−（５−置換−２−ビリミジニル）−１，２，３，４−テトラヒドロナフタレン | |
| JPS59157056A (ja) | 光学活性アルコ−ルのエステル | |
| JPS59141540A (ja) | 三環カルボン酸エステル誘導体 | |
| JPS60172971A (ja) | アルキルビピリミジン類 | |
| JPS60204769A (ja) | ハロゲノピリミジン誘導体 | |
| JPS6032722A (ja) | ６，６’−ジ置換−２，２’−ビナフチル | |
| JPS59184165A (ja) | ５−アルキル−２−（４−フルオロフエニル）−ピリミジン | |
| JPS6050177B2 (ja) | 液晶化合物 | |
| JPS60190766A (ja) | ２，５′−ジ置換−５，２′−ピピリミジニル類 | |
| JPS60199879A (ja) | 二置換ピリミジン類 | |
| JPS60197637A (ja) | β−（４−置換フエニル）プロピオン酸フエニルエステル誘導体 | |
| JPS60188347A (ja) | α−メチル−β−（４−置換フエニル）プロピオン酸のハロゲノフエニルのエステル誘導体 | |
| JPS6136251A (ja) | ３−ハロゲノ−４−シアノフエノ−ルのエステル誘導体 | |
| JPS6168447A (ja) | フエノオキシ酢酸エステル誘導体 | |
| JPH01193254A (ja) | アリルピリミジニルフェノールのエステル誘導体 | |
| JPH045015B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS60152460A (ja) | トランス−４−（４−置換フエニル）シクロヘキサンカルボン酸−４−クロロチオフエニルエステル |