JP4368679B2 - ホトクロミックビス−ナフトピラン化合物およびそれらの製造方法 - Google Patents
ホトクロミックビス−ナフトピラン化合物およびそれらの製造方法 Download PDFInfo
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- JP4368679B2 JP4368679B2 JP2003524988A JP2003524988A JP4368679B2 JP 4368679 B2 JP4368679 B2 JP 4368679B2 JP 2003524988 A JP2003524988 A JP 2003524988A JP 2003524988 A JP2003524988 A JP 2003524988A JP 4368679 B2 JP4368679 B2 JP 4368679B2
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- Prior art keywords
- alkyl
- alkoxy
- phenyl
- substituted
- aryl
- 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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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 29
- IJJMQFOFFIWMNN-UHFFFAOYSA-N 12-oxapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2(11),3,5,7,9,15,17,19,21-decaene Chemical class C1=CC=CC2=C3COC4=CC=C(C=CC=C5)C5=C4C3=CC=C21 IJJMQFOFFIWMNN-UHFFFAOYSA-N 0.000 title description 6
- -1 phenyl vinyl Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052760 oxygen Chemical group 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- IFBNDCRGSQAVKS-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-[5-[5-[3-(2-fluorophenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound FC1=CC=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C(=CC=CC=2)F)C=CC2=C3C=CC=CC3=CC=C2O1 IFBNDCRGSQAVKS-UHFFFAOYSA-N 0.000 claims description 3
- KVBYJSOLTLFGAS-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-[5-[5-[3-(4-fluorophenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(F)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(F)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 KVBYJSOLTLFGAS-UHFFFAOYSA-N 0.000 claims description 3
- YEQJONKQJLKCHR-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[5-[5-[3-(4-methoxyphenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(OC)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 YEQJONKQJLKCHR-UHFFFAOYSA-N 0.000 claims description 3
- NYUMKEXJTPXMJR-UHFFFAOYSA-N 3-(4-methylphenyl)-3-[5-[5-[3-(4-methylphenyl)benzo[f]chromen-3-yl]thiophen-2-yl]thiophen-2-yl]benzo[f]chromene Chemical compound C1=CC(C)=CC=C1C1(C=2SC(=CC=2)C=2SC(=CC=2)C2(C=CC3=C4C=CC=CC4=CC=C3O2)C=2C=CC(C)=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NYUMKEXJTPXMJR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 6
- 238000005562 fading Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KLTRLSNGWVFQNG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-thiophen-2-ylprop-2-yn-1-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C#C)C1=CC=CS1 KLTRLSNGWVFQNG-UHFFFAOYSA-N 0.000 description 4
- VXMHYFQHZLBFFE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 VXMHYFQHZLBFFE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IMTDPCTYUISKDT-UHFFFAOYSA-N bis[3-(4-methoxyphenyl)thiophen-2-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)C2=C(C=CS2)C=2C=CC(OC)=CC=2)SC=C1 IMTDPCTYUISKDT-UHFFFAOYSA-N 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NRSHWKZBFDZELB-UHFFFAOYSA-N 3-(4-methylphenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(C)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NRSHWKZBFDZELB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000001228 spectrum Methods 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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
- IUOBPBSTMKHCNS-UHFFFAOYSA-N bis[4-methoxy-2-(5-thiophen-2-ylthiophen-2-yl)phenyl]methanone Chemical compound C=1C=C(C=2SC=CC=2)SC=1C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1C(S1)=CC=C1C1=CC=CS1 IUOBPBSTMKHCNS-UHFFFAOYSA-N 0.000 description 2
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- 238000001953 recrystallisation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- WMJSQDMPJLFVEJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3H-benzo[f]chromene Chemical compound COc1ccc(cc1)C1=CCOc2ccc3ccccc3c12 WMJSQDMPJLFVEJ-UHFFFAOYSA-N 0.000 description 1
- WKMZFSBJVUDCAI-UHFFFAOYSA-N 1-naphthalen-2-yl-1-(5-thiophen-2-ylthiophen-2-yl)prop-2-yn-1-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C(C#C)(O)C(S1)=CC=C1C1=CC=CS1 WKMZFSBJVUDCAI-UHFFFAOYSA-N 0.000 description 1
- FJTNVEFEPJXYLG-UHFFFAOYSA-N 1-naphthalen-2-yl-3H-benzo[f]chromene Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CCOC2=C1C1=CC=CC=C1C=C2 FJTNVEFEPJXYLG-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 1
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 description 1
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- NPWBWRGEKRCJKH-UHFFFAOYSA-N 3-(2-fluorophenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound FC1=CC=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 NPWBWRGEKRCJKH-UHFFFAOYSA-N 0.000 description 1
- LUIQNLIEDINBMR-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-thiophen-2-ylbenzo[f]chromene Chemical compound C1=CC(F)=CC=C1C1(C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 LUIQNLIEDINBMR-UHFFFAOYSA-N 0.000 description 1
- OZZGYTATBPHFBV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-(5-thiophen-2-ylthiophen-2-yl)benzo[f]chromene Chemical compound C1=CC(OC)=CC=C1C1(C=2SC(=CC=2)C=2SC=CC=2)C=CC2=C3C=CC=CC3=CC=C2O1 OZZGYTATBPHFBV-UHFFFAOYSA-N 0.000 description 1
- JORUZGFDZMBHDR-UHFFFAOYSA-N 3-naphthalen-2-yl-3-(5-thiophen-2-ylthiophen-2-yl)benzo[f]chromene Chemical compound O1C2=CC=C3C=CC=CC3=C2C=CC1(C=1C=C2C=CC=CC2=CC=1)C(S1)=CC=C1C1=CC=CS1 JORUZGFDZMBHDR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002225 anti-radical effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000005325 aryloxy aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical class CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000009661 fatigue test Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002578 polythiourethane polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Eyeglasses (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/945,897 US6747145B2 (en) | 2001-09-04 | 2001-09-04 | Photochromic bis-naphthopyran compounds and methods for their manufacture |
| PCT/US2002/025669 WO2003020718A1 (en) | 2001-09-04 | 2002-08-13 | Photochromic bis-naphthopyran compounds and methods for their manufacture |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005508897A JP2005508897A (ja) | 2005-04-07 |
| JP2005508897A5 JP2005508897A5 (enExample) | 2005-12-22 |
| JP4368679B2 true JP4368679B2 (ja) | 2009-11-18 |
Family
ID=25483666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003524988A Expired - Fee Related JP4368679B2 (ja) | 2001-09-04 | 2002-08-13 | ホトクロミックビス−ナフトピラン化合物およびそれらの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6747145B2 (enExample) |
| EP (1) | EP1423387B1 (enExample) |
| JP (1) | JP4368679B2 (enExample) |
| KR (1) | KR100906205B1 (enExample) |
| CN (1) | CN1296371C (enExample) |
| AU (1) | AU2002332520B2 (enExample) |
| BR (1) | BR0212551A (enExample) |
| CA (1) | CA2459866A1 (enExample) |
| DE (1) | DE60235706D1 (enExample) |
| TW (1) | TW591021B (enExample) |
| WO (1) | WO2003020718A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050258408A1 (en) * | 2001-12-20 | 2005-11-24 | Molock Frank F | Photochromic contact lenses and methods for their production |
| JP4506953B2 (ja) * | 2004-05-28 | 2010-07-21 | 日本電気株式会社 | 共重合高分子膜およびその作製方法 |
| US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
| US8647538B2 (en) | 2005-04-08 | 2014-02-11 | Transitions Optical, Inc. | Photochromic compounds having at least two photochromic moieties |
| US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
| US8147725B2 (en) | 2005-04-08 | 2012-04-03 | Transitions Optical, Inc | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US8158037B2 (en) | 2005-04-08 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US20060226402A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems |
| US20060228557A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
| US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
| US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
| ATE406413T1 (de) * | 2006-01-27 | 2008-09-15 | Ems Chemie Ag | Photochrome formmassen und daraus hergestellte gegenstände |
| US20090244479A1 (en) * | 2008-03-31 | 2009-10-01 | Diana Zanini | Tinted silicone ophthalmic devices, processes and polymers used in the preparation of same |
| US8595218B2 (en) * | 2008-06-12 | 2013-11-26 | Intellectual Ventures Holding 67 Llc | Interactive display management systems and methods |
| US10381134B2 (en) * | 2015-12-29 | 2019-08-13 | Xerox Corporation | Strain gauge polymer comprising photochromic colorant |
| CN110152728A (zh) * | 2019-05-31 | 2019-08-23 | 上海纳米技术及应用国家工程研究中心有限公司 | 具备光致变色性能的复合材料的制备方法及产品和应用 |
| JP7721446B2 (ja) * | 2019-10-17 | 2025-08-12 | 株式会社トクヤマ | フォトクロミック化合物及び該フォトクロミック化合物を含む硬化性組成物 |
| US12326443B2 (en) * | 2020-09-21 | 2025-06-10 | B/E Aerospace Inc. | Detecting antimicrobial surfaces |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567605A (en) | 1966-03-30 | 1971-03-02 | Ralph S Becker | Photochemical process |
| US5066818A (en) | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| JPH0689962A (ja) | 1992-02-28 | 1994-03-29 | Mega Chips:Kk | 半導体装置 |
| US5384077A (en) * | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
| EP0770116B1 (de) * | 1994-07-11 | 1999-09-22 | Optische Werke G. Rodenstock | Diaryl-2h-naphthopyrane |
| US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
| US6281366B1 (en) | 2000-02-29 | 2001-08-28 | Essilor International Compagnie Generale D'optique | Photochromic [3H]naphtho[2,1-b]pyran compounds containing an acetylenic substituent, process for their manufacture, and photochromic materials and articles obtained |
-
2001
- 2001-09-04 US US09/945,897 patent/US6747145B2/en not_active Expired - Fee Related
-
2002
- 2002-08-13 EP EP02797735A patent/EP1423387B1/en not_active Expired - Lifetime
- 2002-08-13 DE DE60235706T patent/DE60235706D1/de not_active Expired - Lifetime
- 2002-08-13 BR BR0212551-0A patent/BR0212551A/pt not_active IP Right Cessation
- 2002-08-13 CA CA002459866A patent/CA2459866A1/en not_active Abandoned
- 2002-08-13 AU AU2002332520A patent/AU2002332520B2/en not_active Ceased
- 2002-08-13 KR KR1020047003278A patent/KR100906205B1/ko not_active Expired - Fee Related
- 2002-08-13 CN CNB028216644A patent/CN1296371C/zh not_active Expired - Fee Related
- 2002-08-13 JP JP2003524988A patent/JP4368679B2/ja not_active Expired - Fee Related
- 2002-08-13 WO PCT/US2002/025669 patent/WO2003020718A1/en not_active Ceased
- 2002-09-03 TW TW091119985A patent/TW591021B/zh not_active IP Right Cessation
-
2003
- 2003-10-28 US US10/695,062 patent/US6939007B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0212551A (pt) | 2004-10-19 |
| TW591021B (en) | 2004-06-11 |
| DE60235706D1 (de) | 2010-04-29 |
| CN1296371C (zh) | 2007-01-24 |
| AU2002332520B2 (en) | 2007-04-26 |
| US6939007B2 (en) | 2005-09-06 |
| KR20040041601A (ko) | 2004-05-17 |
| EP1423387B1 (en) | 2010-03-17 |
| US20030078441A1 (en) | 2003-04-24 |
| KR100906205B1 (ko) | 2009-07-07 |
| US20040084660A1 (en) | 2004-05-06 |
| US6747145B2 (en) | 2004-06-08 |
| CA2459866A1 (en) | 2003-03-13 |
| JP2005508897A (ja) | 2005-04-07 |
| WO2003020718A1 (en) | 2003-03-13 |
| CN1671699A (zh) | 2005-09-21 |
| EP1423387A1 (en) | 2004-06-02 |
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