JP2016079144A - 新規オキソカーボン系化合物 - Google Patents
新規オキソカーボン系化合物 Download PDFInfo
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- JP2016079144A JP2016079144A JP2014213954A JP2014213954A JP2016079144A JP 2016079144 A JP2016079144 A JP 2016079144A JP 2014213954 A JP2014213954 A JP 2014213954A JP 2014213954 A JP2014213954 A JP 2014213954A JP 2016079144 A JP2016079144 A JP 2016079144A
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- oxocarbon
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- -1 oxocarbon compound Chemical class 0.000 title abstract description 200
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 56
- 125000001424 substituent group Chemical group 0.000 claims abstract description 30
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 24
- 125000004429 atom Chemical group 0.000 claims abstract description 13
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 11
- 125000000962 organic group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 239000000975 dye Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 150000001924 cycloalkanes Chemical class 0.000 description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- RBSLJAJQOVYTRQ-UHFFFAOYSA-N croconic acid Chemical compound OC1=C(O)C(=O)C(=O)C1=O RBSLJAJQOVYTRQ-UHFFFAOYSA-N 0.000 description 8
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 8
- SPGDADSXZDUHLA-UHFFFAOYSA-N 7h-acenaphthyleno[2,1-b]pyrrole Chemical compound C1=CC(C=2C=CNC=22)=C3C2=CC=CC3=C1 SPGDADSXZDUHLA-UHFFFAOYSA-N 0.000 description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000005309 thioalkoxy group Chemical group 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- UNWYRONHIKZNPS-UHFFFAOYSA-N 1-(2-methoxyphenyl)-2H-isoindole Chemical compound COC1=CC=CC=C1C2=C3C=CC=CC3=CN2 UNWYRONHIKZNPS-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 2
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003828 azulenyl group Chemical group 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
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 238000009472 formulation 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
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000003427 indacenyl group Chemical group 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 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 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 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
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 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 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004338 2,2,3-trimethylbutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- GJWKQQZDZGZCIZ-UHFFFAOYSA-N C1=CC=C2C([S])=CC=CC2=C1 Chemical compound C1=CC=C2C([S])=CC=CC2=C1 GJWKQQZDZGZCIZ-UHFFFAOYSA-N 0.000 description 1
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910000063 azene Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- VIQRCOQXIHFJND-UHFFFAOYSA-N bicyclo[2.2.2]oct-2-ene Chemical compound C1CC2CCC1C=C2 VIQRCOQXIHFJND-UHFFFAOYSA-N 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001444 catalytic combustion detection Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000003074 decanoyl group Chemical group [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(*)=O 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])[H] 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 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 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])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
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- UMRZSTCPUPJPOJ-UHFFFAOYSA-N norbornane Chemical compound C1CC2CCC1C2 UMRZSTCPUPJPOJ-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])[H] 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
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
【解決手段】式3で表される、スクアリリウム骨格又はクロコニウム骨格に、直接ピロール環が結合している化合物。
(Aはピロール環のβ位の2つの炭素原子が他の原子と共に形成する環構造;XはH又は有機基;YはH、電子求引性基又は有機置換基;*は結合部位)
【選択図】なし
Description
Aは、ピロール環のβ位の2つの炭素原子が他の原子と共に形成する環構造を示し、
Xは水素原子又は有機基であり、
Yは水素原子、電子求引性基又は有機置換基であり、
*は結合部位を表す。)
本発明に係る新規のオキソカーボン系化合物は、スクアリリウム骨格を有する下記式(1)又はクロコニウム骨格を有する下記式(2)で表されることを特徴とする。
Aは、ピロール環のβ位の2つの炭素原子が他の原子と共に形成する環構造を示し、
Xは水素原子又は有機基であり、
Yは水素原子、電子求引性基又は有機置換基であり、
*は結合部位を表す。)
Z1、Z2は、炭素数1〜10のアルキレン基が好ましく、より好ましくは炭素数2〜5のアルキレン基である。好ましいアルキレン基を例示すると、例えば、−CH2−、−CH2CH2−、−CH2CH2CH2−、−CH2CH2CH2CH2−、−CH(CH2)CH2−、−CH(C2H5)CH2−、−C(CH2)2CH2−、−CH2CH2CH2CH2CH2−、−CH2CH2CH2CH2CH2CH2−、等が挙げられる。中でも−CH2−(メチレン基)、−CH2CH2−(エチレン基)、−CH(CH2)CH2−(プロピレン基)又は−CH2CH2CH2−(トリメチレン基)が好ましく、より好ましくは−CH2−(メチレン基)又は−CH2CH2−(エチレン基)である。
また、Z3は、炭素数が1〜20のアルキル基が好ましく、より好ましくは炭素数1〜10のアルキル基であり、好ましいアルキル基を例示すると、例えば、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、s−ブチル基、t−ブチル基、n−ペンチル基であり、より好ましくはメチル基又はエチル基である。
nは0〜4の整数であるが、より好ましくは0〜2であり、更に好ましくは0又は1である。
このようなアルコキシアルキル基としては、例えば、メトキシエチル基、エトキシエチル基、メトキシエトキシメチル基、メトキシエトキシメチル基、エトキシエトキシエチル基等が挙げられる。
本発明に係るオキソカーボン系化合物は、下記式(4):
紫外−可視吸収スペクトル;日立ハイテクノロジー社製 型式「U−2810」、日本分光社製 型式「v−570型」
赤外吸収スペクトル;堀場製作所製 型式「FT-720」
NMRスペクトル;日本電子社製 型式「JNM−AL400」、日本電子社製 型式「JNM−EX400」、バリアン・テクノロジーズ社製 型式「マーキュリー2000」
マススペクトル;日本電子社製、型式「JMS−MS 700型」
(MALDI−TOF)マススペクトル;アプライド・バイオシステムズ社製、型式「Voyager−DETM−PRO」
実施例1 アセナフトピロールを有するスクアリリウム色素の合成
反応容器にアセナフトピロール20(413mg,1.1mmol)を加え、窒素置換した。dryTHFを30mL加え遮光し、LiAlH4(213mg,5.6mmol)を加えて一晩加熱還流した。室温に戻した後、飽和酒石酸Na水溶液でクエンチし、酢酸エチルで抽出後、水と飽和食塩水で洗浄した。Na2SO4で乾燥させ、減圧濃縮し、目的のアセナフトピロール2を得た(収量356mg,1.1mmol,収率quant.)。
Mol.Form.:(Exact Mass:317.2143,Mol.Wt.:317.4672)
Appearance:淡黄緑色固体
1H NMR (CDCl3,400MHz):δ=7.72 (brs,1H),7.60(d,J=1.2Hz,1H),7.52(m,2H),7.50(m,1H),6.85(d,J=2.3Hz,1H),2.54(s,3H),1.45(s, 9H),1.43(s, 9H)
反応容器にスクアリン酸1(62.4mg,0.547mmol)とアセナフトピロール2(0.356g,1.13mmol)を加えて窒素置換した。n−BuOH及びtolueneを1:1の割合で20mL加え、加熱還流した。1時間後に原料のアセナフトピロールが消えているのをTLCで確認した後、加熱をやめ室温に戻して減圧濃縮した。MeOHで洗浄し生成物と思われる暗緑色の固体を得、さらにCHCl3/MeOHで再結晶させることで化合物3を得た(収量0.2744g,0.383mmol,収率70%)。クロロホルム溶解時の回転異性体存在比は5:3であった。
Mol.Form.:(Exact Mass712.4029:,Mol.Wt.:712.9601)
Appearance:緑色粉末
1H NMR (CDCl3,400MHz):δ=10.19(brs,1H,minor),9.97(brs,1H,major),9.42(s,1H,major),9.24(s,1H,minor),7.80−7.78(m,2H),7.73−7.68(m,4H),2.76(s,3H,minor),2.64(s,3H,major),1.63-1.48(m,36H)
UV−vis (CHCl3) λmax,709nm
MS(MALDI−TOF MS):713.0355(M+)
Mol.Form.:(Exact Mass:580.2362, Mol.Wt.:580.6722)
Appearance:緑色粉末
1H NMR (CDCl3,400MHz):δ=10.66(brs,1H),10.38(brs,1H),7.78(m,2H),7.36(m,2H),7.09(m,2H),7.04(m,2H),6.63(m,2H),6.53(m,2H),5.06(m,1H),4.92(m,1H),4.38(m,2H),4.07(s,3H),4.03(s,3H),1.79−1.56(m,8H)
UV−vis (CHCl3) λmax,639nm
MS(MALDI−TOF MS):581.8236(M+),553.8042(M+−28), 524.7811(M+−56)
Mol.Form.:(Exact Mass:524.1736,Mol.Wt.:524.5654)
Appearance:黒色粉末
1H NMR (CDCl3,400MHz):δ=12.38(brs,1H,major),12.12(brs,1H,minor),8.94(d,J=8.1Hz,1H,minor),8.80(d,J=8.1Hz,1H,major),8.14−8.06(m,4H),7.51−7.38(m,6H),7.20−7.10(m,4H),4.19(s,3H,major),4.10(s,3H,minor)
UV−vis (CHCl3) λmax,740nm
MS(MALDI−TOF MS):546.03(M++23)
Mol.Form.:(Exact Mass:580.2362,Mol.Wt.:396.4810)
Appearance:色粉末
1H NMR (CDCl3,400MHz):δ=9.61(brs,1H),9.39 (brs,1H),6.56−6.46(m,4H),4.94(m,1H),4.80 (m,1H),3.90(s,2H),2.36(s,6H),1.65−1.26(m,8H)
UV−vis (CHCl3) λmax, 563nm
MS(MALDI−TOF):368.84(M+−28)
MS(FAB):396(M+), 340(M+−56)
Mol.Form.:(Exact Mass:340.1212,Mol.Wt.:340.3746)
Appearance:黒色粉末
UV−vis (CHCl3) λmax,650nm
yield:109mg(41%)
Mol.Form.:C34H34N2O4(Exact Mass:534.25,Mol.Wt.:534.64)
Appearance:green powder
UV-vis(CHCl3):651nm
実施例7 o−メトキシフェニル−ビシクロピロールを有するクロコニウム色素の合成
Mol.Form.:C39H32N2O5(Exact Mass:608.23,Mol.Wt.:608.68)
Appearance:brown−red powder
1H NMR:(CDCl3,400MHz):δ=13.14(brs,1H),12.83(brs,1H),12.76(brs,1H),12.60(brs,1H),7.94−7.83(m,2H+2H),7.47−7.40(m,2H+2H),7.15−7.06(m,4H+4H),6.71−6.52(m,4H+4H),5.81(m,1H),5.72 (m,1H),5.65 (m,1H),4.47−4.41(m,2H+2H),4.17(s,3H),4.16(s,3H),4.14(s,3H),4.10(s,3H),1.69−1.56(m,8H+8H)
MS(MALDI−TOF): 579.49(M+−28)
UV−vis(CHCl3) λmax,794nm
yield: trace (trace)
Mol.Form.: C39H32N2O5 (Exact Mass:552.17,Mol.Wt.:552.58)
Appearance: block solid
UV−vis(CHCl3) λmax,866nm
Mol.Form.: C51H54N2O3 (Exact Mass:742.41,Mol.Wt.:742.99)
Appearance: brown−red powder
1H NMR:(CDCl3,400MHz):δ(syn)=12.60(brs,2H,major),9.67(s,2H,major),7.82(s,2H,major),7.68(s,2H,major),7.43(s,2H,major),2.55(s,6H,major),1.62(s,18H,major),1.41(s,18H,major),δ(anti)=13.41(brs,1H,minor),11.76(brs,1H,minor),9.74(s,1H,minor),9.64(s,1H,minor),7.86(s,1H,minor),7.83(s,1H,minor),7.77(s,1H,minor),7.72(s,1H,minor),7.69(s,1H,minor),7.63(s,1H,minor),2.82(s,3H,minor),2.57(s,3H,minor),1.64(s,9H,minor),1.60(s,9H,minor),1.50(s,9H,minor),1.47(s,9H,minor)
MS (FAB): 742(M+)
UV−vis (CHCl3) λmax,854 nm
yield:408mg(57%)
Mol.Form.:C35H32N2O5(Exact Mass:560.23,Mol.Wt.:560.64)
Appearance:brown−red powder
UV-vis(CHCl3):800nm
下記処方1〜5で得た塗膜をキセノンウェザーメーター(スガ試験機株式会社製、X75SC)にセットし、耐光性試験を実施した。評価条件は60℃雰囲気下で24時間の光照射とした。
製造例1(ポリイミドのジメチルアセトアミド溶液)
1,2,4,5−シクロヘキサンテトラカルボン酸(東京化成製、純度98%、mw=260.20)5部と無水酢酸(和光純薬製)44部とをフラスコに仕込み、攪拌しながら反応器内を窒素ガスで置換した。窒素ガス雰囲気下で溶剤の還流温度まで昇温し、10分間溶剤を還流させた。攪拌しながら室温まで冷却し、結晶を析出させた。析出した結晶を固液分離し、乾燥して目的物(1,2,4,5−シクロヘキサンテトラカルボン酸二無水物)の結晶を得た。温度計、撹拌器、窒素導入管、側管付き滴下ロート、ディーンスターク、冷却管を備えたフラスコに、窒素気流下、4,4’−ジアミノジフェニルエーテル(和光純薬製、mw=200.24)8.9部と、溶剤としてジメチルアセトアミド76部を仕込んで溶解させた後、1,2,4,5−シクロヘキサンテトラカルボン酸二無水物(mw=224.17)10部を室温にて、固体のまま1時間かけて分割投入し、室温下2時間撹拌した。共沸脱水剤としてトルエンを26部添加して130℃で3時間反応を行い、ディーンスタークで還流して共沸する生成水を分離した。194℃に昇温しながらキシレンを留去した後、冷却しポリイミドのジメチルアセトアミド溶液を得た。
日本触媒製アクリビュア(登録商標:「RN」)10部をジオキサン90部と混合、撹拌して、アクリビュア(RN)のジオキサン溶液を得た。
処方1(化合物3を含む樹脂組成物)
製造例1で得たポリイミドのジメチルアセトアミド溶液をジメチルアセトアミドで希釈し、濃度を8%に調整した。この溶液12.31部と実施例1で得た化合物(3)0.015部を混合し、化合物を溶解した。この溶液をろ過して不溶分等を除いた後、ガラス基板上にスピンコートし、150℃で20分間焼成し、塗膜を得た。
製造例2で得たアクリビュアのジオキサン溶液9.85部と、実施例1で得た化合物(3)0.015部を混合し、化合物を溶解した。この溶液をろ過して不溶分等を除いた後、ガラス基板上にスピンコートし、150℃で20分間焼成し、塗膜を得た。
製造例2で得たアクリビュアのジオキサン溶液9.85部と、実施例8で得た化合物(12)0.015部を混合し、化合物を溶解した。この溶液をろ過して不溶分等を除いた後、ガラス基板上にスピンコートし、150℃で20分間焼成し、塗膜を得た。
製造例1で得たポリイミドのジメチルアセトアミド溶液をジメチルアセトアミドで希釈し、濃度を8%に調整した。この溶液12.31部と下記式で表されるスクアリリウム色素0.015部を混合し、該色素を溶解した。この溶液をろ過して不溶分等を除いた後、ガラス基板上にスピンコートし、150℃で20分間焼成し、塗膜を得た。
製造例1で得たポリイミドのジメチルアセトアミド溶液をジメチルアセトアミドで希釈し、濃度を8%に調整した。この溶液12.31部と下記式で表されるクロコニウム色素0.015部を混合し、色素を溶解した。この溶液をろ過して不溶分等を除いた後、ガラス基板上にスピンコートし、150℃で20分間焼成し、塗膜を得た。
処方1(図1) 44%
処方2(図2) 72%
処方3(図3) 92%
処方4(図4) 2%
処方5(図5) 56%
Claims (3)
- スクアリリウム骨格を有する下記式(1)又はクロコニウム骨格を有する下記式(2)で表されることを特徴とするオキソカーボン系化合物。
Aは、ピロール環のβ位の2つの炭素原子が他の原子と共に形成する環構造を示し、
Xは水素原子又は有機基であり、
Yは水素原子、電子求引性基又は有機置換基であり、
*は結合部位を表す。) - 前記Aは、芳香族環、脂環式炭化水素環、芳香族環もしくは脂環式炭化水素環を構成する炭素原子の少なくとも1個以上が、N、S及びOから選ばれる少なくとも1種以上の原子に置き換わった複素環、及びこれらの環が他の環と縮環している環である請求項1に記載のオキソカーボン系化合物。
- 前記Xが水素原子であり、前記Yが置換基を有していてもよい炭素数1〜4のアルキル基、又は置換基を有していてもよいアリール基である請求項1又は2に記載のオキソカーボン系化合物。
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