JPS61221171A - ２−フエニルピリジン誘導体 - Google Patents
２−フエニルピリジン誘導体Info
- Publication number
- JPS61221171A JPS61221171A JP60062553A JP6255385A JPS61221171A JP S61221171 A JPS61221171 A JP S61221171A JP 60062553 A JP60062553 A JP 60062553A JP 6255385 A JP6255385 A JP 6255385A JP S61221171 A JPS61221171 A JP S61221171A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- reaction
- ethyl
- compounds
- stirring
- 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
- 150000005360 2-phenylpyridines Chemical class 0.000 title claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 33
- 239000004973 liquid crystal related substance Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- -1 Sodium-bromopentane Chemical compound 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- STYJKBMRWQQJIS-UHFFFAOYSA-N 1-(4-bromophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(Br)C=C1 STYJKBMRWQQJIS-UHFFFAOYSA-N 0.000 description 2
- SGCJPYYTVBHQGE-UHFFFAOYSA-N 1-bromo-4-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C=C1 SGCJPYYTVBHQGE-UHFFFAOYSA-N 0.000 description 2
- VCLBNKVFUHIBLR-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-5-pentylpyridine Chemical compound N1=CC(CCCCC)=CC=C1C1=CC=C(OCC)C=C1 VCLBNKVFUHIBLR-UHFFFAOYSA-N 0.000 description 2
- CGTLZHCHQURDHP-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-5-pentylpyridine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CC=C(CCCCC)C=N1 CGTLZHCHQURDHP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000004768 bromobenzenes Chemical class 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- XQRFASOUJIKXRE-UHFFFAOYSA-N (4-cyanophenyl) 4-butylbenzoate Chemical compound C1=CC(CCCC)=CC=C1C(=O)OC1=CC=C(C#N)C=C1 XQRFASOUJIKXRE-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HQXWRAOZXKCCPF-UHFFFAOYSA-N 2-(4-butylphenyl)-5-octylpyridine 5-octyl-2-(4-pentylphenyl)pyridine 5-octyl-2-(4-propylphenyl)pyridine Chemical compound C(CCCC)C1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC.C(CCC)C1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC.C(CC)C1=CC=C(C=C1)C1=NC=C(C=C1)CCCCCCCC HQXWRAOZXKCCPF-UHFFFAOYSA-N 0.000 description 1
- FHNPQXOYUGJBFD-UHFFFAOYSA-N 2-(4-hexylphenyl)-5-octylpyridine Chemical compound N1=CC(CCCCCCCC)=CC=C1C1=CC=C(CCCCCC)C=C1 FHNPQXOYUGJBFD-UHFFFAOYSA-N 0.000 description 1
- JBZWENJZNAKLFF-UHFFFAOYSA-N 2-(4-octylphenyl)-5-pentylpyridine Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(CCCCC)C=N1 JBZWENJZNAKLFF-UHFFFAOYSA-N 0.000 description 1
- SUFGHKDXFPUICR-UHFFFAOYSA-N 2-(4-pentoxyphenyl)-5-pentylpyridine Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(CCCCC)C=N1 SUFGHKDXFPUICR-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- GWBJBXLZUHKCDX-UHFFFAOYSA-N 5-ethyl-2-(4-octylphenyl)pyridine Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(CC)C=N1 GWBJBXLZUHKCDX-UHFFFAOYSA-N 0.000 description 1
- HJDQIENRPICGKS-UHFFFAOYSA-N 5-octyl-2-(4-octylphenyl)pyridine Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(CCCCCCCC)C=N1 HJDQIENRPICGKS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- POWSVIZSGKRCPM-UHFFFAOYSA-N lithium;pentylbenzene Chemical compound [Li+].CCCCCC1=CC=[C-]C=C1 POWSVIZSGKRCPM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Landscapes
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60062553A JPS61221171A (ja) | 1985-03-27 | 1985-03-27 | ２−フエニルピリジン誘導体 |
| DE19853524489 DE3524489A1 (de) | 1984-07-12 | 1985-07-09 | 2-phenylpyridinderivate und verfahren zu ihrer herstellung |
| GB08517437A GB2161808B (en) | 1984-07-12 | 1985-07-10 | Liquid crystalline 2-phenylpyridine derivatives |
| CA000486645A CA1254573A (en) | 1984-07-12 | 1985-07-11 | 2-phenylpyridine derivatives |
| FR858510651A FR2568875B1 (fr) | 1984-07-12 | 1985-07-11 | 2-phenylpyridine et compositions de cristal liquide en contenant |
| US06/754,056 US4684220A (en) | 1984-07-12 | 1985-07-11 | 2-phenylpyridine derivatives and liquid crystal compositions including same |
| KR1019850004944A KR900006429B1 (ko) | 1984-07-12 | 1985-07-11 | 2-페닐피리딘 유도체의 제조방법 |
| CH3047/85A CH668968A5 (de) | 1984-07-12 | 1985-07-12 | 2-phenylpyridin-derivate. |
| NL8502011A NL8502011A (nl) | 1984-07-12 | 1985-07-12 | Fenylpyridinederivaten. |
| US07/068,996 US4879060A (en) | 1984-07-12 | 1987-05-22 | 2-phenylpyridine derivatives and liquid crystal compositions including same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60062553A JPS61221171A (ja) | 1985-03-27 | 1985-03-27 | ２−フエニルピリジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61221171A true JPS61221171A (ja) | 1986-10-01 |
| JPH0246032B2 JPH0246032B2 (enrdf_load_stackoverflow) | 1990-10-12 |
Family
ID=13203561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60062553A Granted JPS61221171A (ja) | 1984-07-12 | 1985-03-27 | ２−フエニルピリジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61221171A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62255477A (ja) * | 1986-04-22 | 1987-11-07 | エフ・ホフマン―ラ ロシユ アーゲー | ピリジン誘導体 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6124570A (ja) * | 1984-07-12 | 1986-02-03 | Seiko Epson Corp | ２−フエニルピリジン誘導体 |
| JPS6191170A (ja) * | 1984-10-11 | 1986-05-09 | Seiko Epson Corp | ２−フエニルピリジン誘導体 |
-
1985
- 1985-03-27 JP JP60062553A patent/JPS61221171A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6124570A (ja) * | 1984-07-12 | 1986-02-03 | Seiko Epson Corp | ２−フエニルピリジン誘導体 |
| JPS6191170A (ja) * | 1984-10-11 | 1986-05-09 | Seiko Epson Corp | ２−フエニルピリジン誘導体 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62255477A (ja) * | 1986-04-22 | 1987-11-07 | エフ・ホフマン―ラ ロシユ アーゲー | ピリジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0246032B2 (enrdf_load_stackoverflow) | 1990-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |