CN102585838A - 一种4-[(4-r烷氧基2,3,5,6-四氟苯基)乙基]苯甲酸(4-r1烷氧基)苯酯含氟液晶化合物 - Google Patents
一种4-[(4-r烷氧基2,3,5,6-四氟苯基)乙基]苯甲酸(4-r1烷氧基)苯酯含氟液晶化合物 Download PDFInfo
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- CN102585838A CN102585838A CN2012100081461A CN201210008146A CN102585838A CN 102585838 A CN102585838 A CN 102585838A CN 2012100081461 A CN2012100081461 A CN 2012100081461A CN 201210008146 A CN201210008146 A CN 201210008146A CN 102585838 A CN102585838 A CN 102585838A
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- Prior art keywords
- alkoxyl group
- liquid crystal
- ethyl
- phenyl ester
- phenyl
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 43
- -1 phenyl ester Chemical class 0.000 title claims abstract description 41
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 24
- 239000005711 Benzoic acid Substances 0.000 title abstract 2
- 235000010233 benzoic acid Nutrition 0.000 title abstract 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 3
- 229910052731 fluorine Inorganic materials 0.000 title description 3
- 239000011737 fluorine Substances 0.000 title description 3
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 16
- GHICCUXQJBDNRN-UHFFFAOYSA-N 4-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- HHOXWPCTCQMHNN-UHFFFAOYSA-N C1(=CC=CC=C1)I.[F] Chemical class C1(=CC=CC=C1)I.[F] HHOXWPCTCQMHNN-UHFFFAOYSA-N 0.000 claims description 11
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical class FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- GFSFKWHVGTYIOS-UHFFFAOYSA-N 2-(2,3,4,5,6-pentafluorophenyl)ethynyl-tris(trifluoromethyl)silane Chemical group FC([Si](C(F)(F)F)(C(F)(F)F)C#CC1=C(C(=C(C(=C1F)F)F)F)F)(F)F GFSFKWHVGTYIOS-UHFFFAOYSA-N 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 235000015320 potassium carbonate Nutrition 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000005224 alkoxybenzenes Chemical class 0.000 claims description 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- UZIXCCMXZQWTPB-UHFFFAOYSA-N trimethyl(2-phenylethynyl)silane Chemical group C[Si](C)(C)C#CC1=CC=CC=C1 UZIXCCMXZQWTPB-UHFFFAOYSA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000010409 thin film Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000002194 synthesizing effect Effects 0.000 description 9
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FVMNKQOHKRPJPB-UHFFFAOYSA-N C(CC)OC1=C(C(=C(C(=C1F)F)C#CC1=CC=C(C=C1)C(=O)O)F)F Chemical compound C(CC)OC1=C(C(=C(C(=C1F)F)C#CC1=CC=C(C=C1)C(=O)O)F)F FVMNKQOHKRPJPB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DQZWCBXFYJQLCB-UHFFFAOYSA-N 4-[2-(2,3,5,6-tetrafluoro-4-pentoxyphenyl)ethyl]benzoic acid Chemical compound C(CCCC)OC1=C(C(=C(C(=C1F)F)CCC1=CC=C(C=C1)C(=O)O)F)F DQZWCBXFYJQLCB-UHFFFAOYSA-N 0.000 description 1
- IEUKKNAJTRVWGJ-UHFFFAOYSA-N C(CC)OC1=C(C(=C(C(=C1F)F)CCC1=CC=C(C=C1)C(=O)O)F)F Chemical compound C(CC)OC1=C(C(=C(C(=C1F)F)CCC1=CC=C(C=C1)C(=O)O)F)F IEUKKNAJTRVWGJ-UHFFFAOYSA-N 0.000 description 1
- PCJMYZDTKCWPRP-UHFFFAOYSA-N C(CCC)OC1=C(C(=C(C(=C1F)F)CCC1=CC=C(C=C1)C(=O)O)F)F Chemical compound C(CCC)OC1=C(C(=C(C(=C1F)F)CCC1=CC=C(C=C1)C(=O)O)F)F PCJMYZDTKCWPRP-UHFFFAOYSA-N 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN201210008146.1A CN102585838B (zh) | 2012-01-12 | 2012-01-12 | 一种4-[(4-烷氧基2,3,5,6-四氟苯基)乙基]苯甲酸(4-烷氧基)苯酯含氟液晶化合物 |
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CN201210008146.1A CN102585838B (zh) | 2012-01-12 | 2012-01-12 | 一种4-[(4-烷氧基2,3,5,6-四氟苯基)乙基]苯甲酸(4-烷氧基)苯酯含氟液晶化合物 |
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CN102585838B CN102585838B (zh) | 2014-01-08 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827614A (zh) * | 2012-09-24 | 2012-12-19 | 上海天问化学有限公司 | 含有2,3,5,6-四氟亚苯基的负性液晶、合成方法及应用 |
CN103333697A (zh) * | 2013-07-16 | 2013-10-02 | 上海天问化学有限公司 | 含有2,3,5,6-四氟二苯乙炔的向列型负性液晶、合成方法及应用 |
CN103539641A (zh) * | 2013-10-16 | 2014-01-29 | 西安彩晶光电科技股份有限公司 | 液晶化合物二氟-[(4-烷氧基-2,3,5,6-四氟苯基)乙基)-3,5-二氟苯基-3,4,5-三氟苯氧基]甲烷的合成方法 |
CN104610975B (zh) * | 2013-11-05 | 2017-03-01 | 财团法人工业技术研究院 | 负介电各向异性液晶化合物、液晶显示器、与光电装置 |
CN110903832A (zh) * | 2019-12-20 | 2020-03-24 | 上海瓜呱科技有限公司 | 负性液晶化合物以及含有该化合物的液晶组合物及其应用 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102827614A (zh) * | 2012-09-24 | 2012-12-19 | 上海天问化学有限公司 | 含有2,3,5,6-四氟亚苯基的负性液晶、合成方法及应用 |
CN103333697A (zh) * | 2013-07-16 | 2013-10-02 | 上海天问化学有限公司 | 含有2,3,5,6-四氟二苯乙炔的向列型负性液晶、合成方法及应用 |
CN103333697B (zh) * | 2013-07-16 | 2015-06-03 | 福建省邵武市永晶化工有限公司 | 含有2,3,5,6-四氟二苯乙炔的向列型负性液晶、合成方法及应用 |
CN103539641A (zh) * | 2013-10-16 | 2014-01-29 | 西安彩晶光电科技股份有限公司 | 液晶化合物二氟-[(4-烷氧基-2,3,5,6-四氟苯基)乙基)-3,5-二氟苯基-3,4,5-三氟苯氧基]甲烷的合成方法 |
CN103539641B (zh) * | 2013-10-16 | 2014-12-17 | 西安彩晶光电科技股份有限公司 | 液晶化合物二氟-[(4-烷氧基-2,3,5,6-四氟苯基)乙基)-3,5-二氟苯基-3,4,5-三氟苯氧基]甲烷的合成方法 |
CN104610975B (zh) * | 2013-11-05 | 2017-03-01 | 财团法人工业技术研究院 | 负介电各向异性液晶化合物、液晶显示器、与光电装置 |
CN110903832A (zh) * | 2019-12-20 | 2020-03-24 | 上海瓜呱科技有限公司 | 负性液晶化合物以及含有该化合物的液晶组合物及其应用 |
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