JP4860464B2 - ベンゾクロメン誘導体 - Google Patents
ベンゾクロメン誘導体 Download PDFInfo
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- JP4860464B2 JP4860464B2 JP2006501636A JP2006501636A JP4860464B2 JP 4860464 B2 JP4860464 B2 JP 4860464B2 JP 2006501636 A JP2006501636 A JP 2006501636A JP 2006501636 A JP2006501636 A JP 2006501636A JP 4860464 B2 JP4860464 B2 JP 4860464B2
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- Japan
- Prior art keywords
- liquid crystal
- formula
- zli
- independently
- bromo
- 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.)
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- VCDAWCBLCCVSKE-UHFFFAOYSA-N 2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=CCO2 VCDAWCBLCCVSKE-UHFFFAOYSA-N 0.000 title description 7
- -1 heptane-2,4-diyl Chemical group 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 93
- 239000004973 liquid crystal related substance Substances 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 25
- 0 CC1CCC(**)CC1 Chemical compound CC1CCC(**)CC1 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000013078 crystal Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 16
- 239000012071 phase Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- OCODJNASCDFXSR-UHFFFAOYSA-N 1-bromo-2-fluoro-4-iodobenzene Chemical compound FC1=CC(I)=CC=C1Br OCODJNASCDFXSR-UHFFFAOYSA-N 0.000 description 5
- QNGVPYFPKLUQDX-UHFFFAOYSA-N 6-bromo-2-fluoro-3-methylbenzoic acid Chemical compound CC1=CC=C(Br)C(C(O)=O)=C1F QNGVPYFPKLUQDX-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- DVAPVAYHSYQGCV-UHFFFAOYSA-N 8-ethoxy-4,7-difluoro-3-phenylmethoxybenzo[c]chromen-6-one Chemical compound FC1=C2OC(=O)C3=C(F)C(OCC)=CC=C3C2=CC=C1OCC1=CC=CC=C1 DVAPVAYHSYQGCV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000008648 triflates Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- GHQPLVWOWSSUHW-UHFFFAOYSA-N (6-bromo-2-fluoro-3-pentylphenyl) 6-bromo-2-fluoro-3-methylbenzoate Chemical compound CCCCCC1=CC=C(Br)C(OC(=O)C=2C(=C(C)C=CC=2Br)F)=C1F GHQPLVWOWSSUHW-UHFFFAOYSA-N 0.000 description 3
- PQYGFFABMUEQON-UHFFFAOYSA-N 1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene Chemical compound CCCCOC1=CC=C(Br)C(OCOCCOC)=C1F PQYGFFABMUEQON-UHFFFAOYSA-N 0.000 description 3
- DQJSFSVPQDIUOD-UHFFFAOYSA-N 2,3-difluoro-2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=C(F)C(F)O2 DQJSFSVPQDIUOD-UHFFFAOYSA-N 0.000 description 3
- NOCFJMVWLRFUDI-UHFFFAOYSA-N 3-butoxy-4,6,6,7-tetrafluoro-8-(4-pentylcyclohexyl)benzo[c]chromene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2(F)F)C2=C1F NOCFJMVWLRFUDI-UHFFFAOYSA-N 0.000 description 3
- PFCOCJSPOJYUGG-UHFFFAOYSA-N 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)benzo[c]chromen-6-one Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2=O)C2=C1F PFCOCJSPOJYUGG-UHFFFAOYSA-N 0.000 description 3
- CABLNMPDNZPSOT-UHFFFAOYSA-N 3-butoxy-4,7-difluoro-8-(4-pentylcyclohexyl)benzo[c]chromene-6-thione Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C(=C(F)C(OCCCC)=CC=2)OC2=S)C2=C1F CABLNMPDNZPSOT-UHFFFAOYSA-N 0.000 description 3
- ZMTIHOQUIPYSQK-UHFFFAOYSA-N 4-bromo-1-ethoxy-2-fluorobenzene Chemical compound CCOC1=CC=C(Br)C=C1F ZMTIHOQUIPYSQK-UHFFFAOYSA-N 0.000 description 3
- KWDPNPVCQGEUKZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(4-pentylcyclohexen-1-yl)benzene Chemical compound C1C(CCCCC)CCC(C=2C(=CC(Br)=CC=2)F)=C1 KWDPNPVCQGEUKZ-UHFFFAOYSA-N 0.000 description 3
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-UHFFFAOYSA-N 0.000 description 3
- KXFJNXXTTNGXTQ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-pentylbenzene Chemical compound CCCCCC1=CC=C(Br)C=C1F KXFJNXXTTNGXTQ-UHFFFAOYSA-N 0.000 description 3
- HCVUDNMNSPYSHS-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylmethoxybenzene Chemical compound FC1=CC(Br)=CC=C1OCC1=CC=CC=C1 HCVUDNMNSPYSHS-UHFFFAOYSA-N 0.000 description 3
- NQHXLQOYPJHTGF-UHFFFAOYSA-N 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoic acid Chemical compound C1CC(CCCCC)CCC1C1=CC=C(Br)C(C(O)=O)=C1F NQHXLQOYPJHTGF-UHFFFAOYSA-N 0.000 description 3
- MKUCVRSKYGZIKK-UHFFFAOYSA-N 6-bromo-2-fluoro-3-pentylphenol Chemical compound CCCCCC1=CC=C(Br)C(O)=C1F MKUCVRSKYGZIKK-UHFFFAOYSA-N 0.000 description 3
- WDWMIQICZJPVHB-UHFFFAOYSA-N 6-bromo-2-fluoro-3-phenylmethoxyphenol Chemical compound OC1=C(Br)C=CC(OCC=2C=CC=CC=2)=C1F WDWMIQICZJPVHB-UHFFFAOYSA-N 0.000 description 3
- XISACNRTNATVPU-UHFFFAOYSA-N 8-ethoxy-4,7-difluoro-6h-benzo[c]chromen-3-ol Chemical compound OC1=CC=C2C3=CC=C(OCC)C(F)=C3COC2=C1F XISACNRTNATVPU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DYSJQUQJVBYIOT-UHFFFAOYSA-N Cc(ccc(C)c1F)c1F Chemical compound Cc(ccc(C)c1F)c1F DYSJQUQJVBYIOT-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- BVNDLKONNFGLBX-WKILWMFISA-N FC=1C(OCC)=CC=C(C2=CC=3)C=1COC2=C(F)C=3OC[C@H]1CC[C@H](C=C)CC1 Chemical compound FC=1C(OCC)=CC=C(C2=CC=3)C=1COC2=C(F)C=3OC[C@H]1CC[C@H](C=C)CC1 BVNDLKONNFGLBX-WKILWMFISA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NWRGTDCZGWVEJQ-UHFFFAOYSA-N 4,7-difluoro-8-methyl-3-pentyl-6h-benzo[c]chromene Chemical compound CC1=CC=C2C3=CC=C(CCCCC)C(F)=C3OCC2=C1F NWRGTDCZGWVEJQ-UHFFFAOYSA-N 0.000 description 2
- HZUFMTWUPUVPDS-UHFFFAOYSA-N 4,7-difluoro-8-methyl-3-pentylbenzo[c]chromen-6-one Chemical compound CC1=CC=C2C3=CC=C(CCCCC)C(F)=C3OC(=O)C2=C1F HZUFMTWUPUVPDS-UHFFFAOYSA-N 0.000 description 2
- LFXZYFFWYVFNJA-UHFFFAOYSA-N 6-bromo-3-butoxy-2-fluorophenol Chemical compound CCCCOC1=CC=C(Br)C(O)=C1F LFXZYFFWYVFNJA-UHFFFAOYSA-N 0.000 description 2
- AMTAVRYIRXKBQJ-UHFFFAOYSA-N 6-bromo-3-ethoxy-2-fluorobenzoic acid Chemical compound CCOC1=CC=C(Br)C(C(O)=O)=C1F AMTAVRYIRXKBQJ-UHFFFAOYSA-N 0.000 description 2
- JTPHMYZEINFFSE-UHFFFAOYSA-N 8-ethoxy-4,6,6,7-tetrafluoro-3-pentylbenzo[c]chromene Chemical compound CCOC1=CC=C2C3=CC=C(CCCCC)C(F)=C3OC(F)(F)C2=C1F JTPHMYZEINFFSE-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- IOWLXRZVKTVUGK-HDJSIYSDSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Br)C=C1F Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Br)C=C1F IOWLXRZVKTVUGK-HDJSIYSDSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NRZIJCCVRBHFCO-UHFFFAOYSA-N methyl 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoate Chemical compound C1CC(CCCCC)CCC1C1=CC=C(Br)C(C(=O)OC)=C1F NRZIJCCVRBHFCO-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- VIWUJKBBJRFTMC-UHFFFAOYSA-N (1,2-difluoro-2-phenylethenyl)benzene Chemical class C=1C=CC=CC=1C(F)=C(F)C1=CC=CC=C1 VIWUJKBBJRFTMC-UHFFFAOYSA-N 0.000 description 1
- TVDGCJHEEOTNED-UHFFFAOYSA-N (6-bromo-2-fluoro-3-phenylmethoxyphenyl) 6-bromo-3-ethoxy-2-fluorobenzoate Chemical compound CCOC1=CC=C(Br)C(C(=O)OC=2C(=C(OCC=3C=CC=CC=3)C=CC=2Br)F)=C1F TVDGCJHEEOTNED-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000020477 pH reduction Effects 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
-
- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10308266.2 | 2003-02-25 | ||
| DE10308266 | 2003-02-25 | ||
| PCT/EP2004/000731 WO2004076438A2 (de) | 2003-02-25 | 2004-01-28 | Benzochromenderivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006520327A JP2006520327A (ja) | 2006-09-07 |
| JP2006520327A5 JP2006520327A5 (enExample) | 2007-03-15 |
| JP4860464B2 true JP4860464B2 (ja) | 2012-01-25 |
Family
ID=32797765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006501636A Expired - Fee Related JP4860464B2 (ja) | 2003-02-25 | 2004-01-28 | ベンゾクロメン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7326447B2 (enExample) |
| EP (1) | EP1618101B1 (enExample) |
| JP (1) | JP4860464B2 (enExample) |
| KR (1) | KR101133905B1 (enExample) |
| DE (1) | DE102004004228A1 (enExample) |
| TW (1) | TWI338034B (enExample) |
| WO (1) | WO2004076438A2 (enExample) |
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| JP4403307B2 (ja) * | 2003-03-28 | 2010-01-27 | Ｄｉｃ株式会社 | ６員環ラクトン骨格を有する化合物を含有する液晶組成物 |
| DE10337346A1 (de) * | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
| JP5379974B2 (ja) | 2004-07-02 | 2013-12-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体、およびそれを備える電気光学的ディスプレイ |
| US7648742B2 (en) | 2004-07-29 | 2010-01-19 | Merck Patent Gmbh | Difluorosubstituted heterocyclic compounds and the use thereof in the form of components in liquid crystalline media |
| EP2258695B1 (de) * | 2004-10-07 | 2013-05-29 | Merck Patent GmbH | Chroman-derivate sowie ihre verwendung in flüssigkristallinen medien |
| USRE46558E1 (en) | 2005-04-28 | 2017-09-26 | Paloma Pharmaceuticals, Inc. | Compositions and methods to treat diseases characterized by cellular proliferation and angiogenesis |
| JP5332206B2 (ja) * | 2005-12-08 | 2013-11-06 | Ｊｎｃ株式会社 | ヒドロクマリン骨格を含有する化合物、液晶組成物、および液晶表示素子 |
| DE102006057027B4 (de) | 2005-12-22 | 2023-07-06 | Merck Patent Gmbh | Benzochromenderivate |
| DE102005062098A1 (de) | 2005-12-22 | 2007-06-28 | Merck Patent Gmbh | Oxaphenanthren-Derivate |
| CN101346366B (zh) * | 2005-12-22 | 2012-11-21 | 默克专利股份有限公司 | 苯并色烯衍生物 |
| KR101417138B1 (ko) * | 2005-12-22 | 2014-07-08 | 메르크 파텐트 게엠베하 | 액정 매질에서의 사용 및 치료 활성 물질로서의 사용을위한 벤조크로멘 유도체 |
| JP2009528381A (ja) * | 2006-02-28 | 2009-08-06 | パロマ ファーマシューティカルズ，インク． | 細胞増殖および血管新生を特徴とする疾患を治療する組成物および方法 |
| DE102008054350A1 (de) | 2007-11-27 | 2009-05-28 | Merck Patent Gmbh | Benzo[f]chromen- und Pyrano[3,2-f]chromen-Derivate |
| AU2009228303B2 (en) * | 2008-03-25 | 2015-08-13 | Paloma Pharmaceuticals, Inc. | Methods of treating fibrotic disorders |
| DE102009022309A1 (de) | 2009-05-22 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| KR101821003B1 (ko) * | 2010-12-21 | 2018-03-08 | 제이엔씨 주식회사 | 디하이드로페난트렌을 갖는 화합물, 액정 조성물 및 액정 표시 소자 |
| WO2012112791A1 (en) | 2011-02-16 | 2012-08-23 | Paloma Pharmaceuticals, Inc. | Radiation countermeasure agents |
| EP2514800B2 (de) * | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| JP5983393B2 (ja) | 2012-01-27 | 2016-08-31 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| TWI452122B (zh) | 2012-02-24 | 2014-09-11 | Dainippon Ink & Chemicals | 液晶組成物 |
| CN104610217A (zh) * | 2015-02-09 | 2015-05-13 | 石家庄诚志永华显示材料有限公司 | 含有环戊基的二苯并吡喃酮衍生物的液晶化合物及其应用 |
| CN105647543A (zh) * | 2016-01-13 | 2016-06-08 | 石家庄诚志永华显示材料有限公司 | 液晶组合物 |
| JP6738044B2 (ja) | 2016-07-22 | 2020-08-12 | Jnc株式会社 | ベンゾピラン骨格を有する液晶性化合物、液晶組成物、および液晶表示素子 |
| CN107253942B (zh) * | 2017-06-19 | 2019-07-12 | 清华大学 | 侧向二氟亚甲基醚桥键双末端烷基环己基联苯衍生物及其制备方法与应用 |
| CN108018048B (zh) * | 2017-12-15 | 2021-11-05 | 石家庄诚志永华显示材料有限公司 | 一种负介电各项异性液晶组合物 |
| CN111484475B (zh) * | 2019-01-28 | 2022-11-04 | 北京八亿时空液晶科技股份有限公司 | 一种液晶化合物及其制备方法与应用 |
| MX2023008677A (es) | 2021-01-27 | 2023-10-03 | Vandria Sa | Derivados de urolitinas y métodos para su uso. |
| CN116179214B (zh) * | 2021-11-29 | 2025-04-25 | 石家庄诚志永华显示材料有限公司 | 一种含有苯并色烯化合物的液晶组合物及其应用 |
| EP4626385A1 (en) | 2022-12-01 | 2025-10-08 | Massachusetts Institute Of Technology | Cleavable comonomer strategy for accelerating removal of gel nail polish |
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| FR95364E (fr) * | 1967-08-11 | 1970-09-11 | Ugine Kuhlmann | Nouveaux colorants méthiniques et leurs procédés de préparation. |
| JPH10236992A (ja) * | 1997-02-25 | 1998-09-08 | Chisso Corp | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| JP2001026587A (ja) * | 1999-07-12 | 2001-01-30 | Chisso Corp | ジベンゾピラン−６−オン誘導体およびそれを含む液晶組成物 |
| US20040099842A1 (en) * | 2000-12-23 | 2004-05-27 | Melanie Klasen-Memmer | Liquid crystalline medium |
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| US5648021A (en) * | 1994-01-17 | 1997-07-15 | Hoechst Aktiengesellschaft | Phenanthrene derivatives and their use in liquid-crystalline mixtures |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
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2004
- 2004-01-28 US US10/546,801 patent/US7326447B2/en not_active Expired - Lifetime
- 2004-01-28 WO PCT/EP2004/000731 patent/WO2004076438A2/de not_active Ceased
- 2004-01-28 EP EP04705793.0A patent/EP1618101B1/de not_active Expired - Lifetime
- 2004-01-28 JP JP2006501636A patent/JP4860464B2/ja not_active Expired - Fee Related
- 2004-01-28 KR KR1020057015682A patent/KR101133905B1/ko not_active Expired - Fee Related
- 2004-01-28 DE DE200410004228 patent/DE102004004228A1/de not_active Withdrawn
- 2004-02-24 TW TW093104656A patent/TWI338034B/zh not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR95364E (fr) * | 1967-08-11 | 1970-09-11 | Ugine Kuhlmann | Nouveaux colorants méthiniques et leurs procédés de préparation. |
| JPH10236992A (ja) * | 1997-02-25 | 1998-09-08 | Chisso Corp | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| JP2001026587A (ja) * | 1999-07-12 | 2001-01-30 | Chisso Corp | ジベンゾピラン−６−オン誘導体およびそれを含む液晶組成物 |
| US20040099842A1 (en) * | 2000-12-23 | 2004-05-27 | Melanie Klasen-Memmer | Liquid crystalline medium |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI338034B (en) | 2011-03-01 |
| JP2006520327A (ja) | 2006-09-07 |
| KR101133905B1 (ko) | 2012-04-10 |
| EP1618101A2 (de) | 2006-01-25 |
| KR20050115872A (ko) | 2005-12-08 |
| TW200418958A (en) | 2004-10-01 |
| DE102004004228A1 (de) | 2004-09-02 |
| WO2004076438A2 (de) | 2004-09-10 |
| US20060177603A1 (en) | 2006-08-10 |
| WO2004076438A3 (de) | 2005-02-24 |
| EP1618101B1 (de) | 2017-12-20 |
| US7326447B2 (en) | 2008-02-05 |
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