JPS6084273A - ２，３−ジシアノ−５−置換ピラジン誘導体 - Google Patents
２，３−ジシアノ−５−置換ピラジン誘導体Info
- Publication number
- JPS6084273A JPS6084273A JP19383983A JP19383983A JPS6084273A JP S6084273 A JPS6084273 A JP S6084273A JP 19383983 A JP19383983 A JP 19383983A JP 19383983 A JP19383983 A JP 19383983A JP S6084273 A JPS6084273 A JP S6084273A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- reacting
- dicyano
- 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 2,3-dicyano-5-substituted pyrazine Chemical class 0.000 title claims abstract description 15
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003216 pyrazines Chemical class 0.000 claims description 3
- 102000016917 Complement C1 Human genes 0.000 claims 1
- 108010028774 Complement C1 Proteins 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 22
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 abstract description 3
- 229940073735 4-hydroxy acetophenone Drugs 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- VACLULPMEXHBMD-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzoic acid Chemical compound C1CC(CCC)CCC1C1=CC=C(C(O)=O)C=C1 VACLULPMEXHBMD-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 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
- 239000005711 Benzoic acid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MTMONFVFAYLRSG-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-oxoacetaldehyde Chemical compound OC1=CC=C(C(=O)C=O)C=C1 MTMONFVFAYLRSG-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
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- OZPPUPJQRJYTNY-UHFFFAOYSA-N 4-pentoxybenzoic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=C1 OZPPUPJQRJYTNY-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 241001063191 Elops affinis Species 0.000 description 1
- 235000002756 Erythrina berteroana Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-M phenyl carbonate Chemical compound [O-]C(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-M 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19383983A JPS6084273A (ja) | 1983-10-17 | 1983-10-17 | ２，３−ジシアノ−５−置換ピラジン誘導体 |
| DE8484109430T DE3481055D1 (de) | 1983-08-22 | 1984-08-08 | 2,3-dicyan-5-substituierte pyrazine und diese enthaltende fluessigkristall-zusammensetzung. |
| EP84109430A EP0136480B1 (en) | 1983-08-22 | 1984-08-08 | 2,3-dicyano-5-substituted pyrazines and liquid crystal composition containing them |
| US06/641,730 US4592857A (en) | 1983-08-22 | 1984-08-17 | 2,3-dicyano-5-substituted pyrazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19383983A JPS6084273A (ja) | 1983-10-17 | 1983-10-17 | ２，３−ジシアノ−５−置換ピラジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6084273A true JPS6084273A (ja) | 1985-05-13 |
| JPH0452269B2 JPH0452269B2 (en]) | 1992-08-21 |
Family
ID=16314592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19383983A Granted JPS6084273A (ja) | 1983-08-22 | 1983-10-17 | ２，３−ジシアノ−５−置換ピラジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6084273A (en]) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04129722U (ja) * | 1991-05-16 | 1992-11-27 | 三菱農機株式会社 | 移動農機におけるリコイル式始動装置 |
| WO2017082246A1 (ja) * | 2015-11-10 | 2017-05-18 | 国立大学法人九州大学 | ジシアノピラジン化合物、発光材料、それを用いた発光素子、および２，５－ジシアノ－３，６－ジハロゲノピラジンの製造方法 |
-
1983
- 1983-10-17 JP JP19383983A patent/JPS6084273A/ja active Granted
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04129722U (ja) * | 1991-05-16 | 1992-11-27 | 三菱農機株式会社 | 移動農機におけるリコイル式始動装置 |
| WO2017082246A1 (ja) * | 2015-11-10 | 2017-05-18 | 国立大学法人九州大学 | ジシアノピラジン化合物、発光材料、それを用いた発光素子、および２，５－ジシアノ－３，６－ジハロゲノピラジンの製造方法 |
| CN108137554A (zh) * | 2015-11-10 | 2018-06-08 | 国立大学法人九州大学 | 二氰基吡嗪化合物、发光材料、使用该发光材料的发光元件、以及2,5－二氰基－3,6－二卤代吡嗪的制造方法 |
| JPWO2017082246A1 (ja) * | 2015-11-10 | 2018-08-30 | 国立大学法人九州大学 | ジシアノピラジン化合物、発光材料、それを用いた発光素子、および２，５−ジシアノ−３，６−ジハロゲノピラジンの製造方法 |
| US10399960B2 (en) | 2015-11-10 | 2019-09-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10497878B2 (en) | 2015-11-10 | 2019-12-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10522763B2 (en) | 2015-11-10 | 2019-12-31 | Kyushu University, National Universit Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| EP3375779A4 (en) * | 2015-11-10 | 2020-11-04 | Kyushu University National University Corporation | DICYANOPYRAZINE COMPOUND, LUMINESCENT MATERIAL, LIGHT EMITTER USING IT AND PROCESS FOR THE PRODUCTION OF 2,5-DICYANO-3,6-DIHALOGENOPYRAZINE |
| JP2021014458A (ja) * | 2015-11-10 | 2021-02-12 | 国立大学法人九州大学 | ジシアノピラジン化合物、発光材料、およびそれを用いた発光素子 |
| CN108137554B (zh) * | 2015-11-10 | 2022-03-18 | 国立大学法人九州大学 | 二氰基吡嗪化合物、发光材料、使用该发光材料的发光元件、以及2,5－二氰基－3,6－二卤代吡嗪的制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0452269B2 (en]) | 1992-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6144845A (ja) | 光学活性化合物 | |
| JPH0417174B2 (en]) | ||
| JPS6084273A (ja) | ２，３−ジシアノ−５−置換ピラジン誘導体 | |
| JPH0368866B2 (en]) | ||
| US4592857A (en) | 2,3-dicyano-5-substituted pyrazines | |
| JPH0239497B2 (ja) | 44*toransuu4**arukirushikurohekishiru*ansokukosan2*44jiharogenofueniruesuteru | |
| JPS58121272A (ja) | ３−クロロ−６−ヒドロキシピリジンのエステル誘導体 | |
| JPS58135837A (ja) | ４−（β−アルキルオキシエトキシ）安息香酸４′−アルキルフエニルエステル類 | |
| JP4094742B2 (ja) | エステル化合物ならびにそれを含有する液晶組成物 | |
| JPS62175465A (ja) | 新規エステル化合物 | |
| JPH0142261B2 (en]) | ||
| JP2500687B2 (ja) | ビシクロヘキシルトラン誘導体 | |
| JPH0350734B2 (en]) | ||
| JPH0142941B2 (en]) | ||
| JP4023887B2 (ja) | エステル化合物およびそれを含有する液晶組成物 | |
| JPS642595B2 (en]) | ||
| JPS58210045A (ja) | ４−α，α，α−トリフルオロメチル安息香酸−４−（トランス−４′−アルキルシクロヘキシル）フエニルエステル | |
| JPS60197651A (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３−フルオロ−４−シアノフエニルエステル | |
| JP2819645B2 (ja) | ピリミジン誘導体およびそれを含有する液晶組成物 | |
| JP4763943B2 (ja) | エステル化合物およびそれを含有する液晶組成物 | |
| JPS58188841A (ja) | ３，４−ジクロロ安息香酸トランス−４−（トランス−４′−アルキルシクロヘキシル）フエニルエステル | |
| JPS62286943A (ja) | ４′−置換ビフエニルクロチルエ−テル誘導体 | |
| JPS6110533A (ja) | 液晶性エステル化合物およびその組成物 | |
| JPS6346741B2 (en]) | ||
| JPS6150953A (ja) | ４−アルキル安息香酸３−フルオロ−４−シアノフエニルエステル |