JP6956960B2 - 紫外線吸収剤 - Google Patents
紫外線吸収剤 Download PDFInfo
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- JP6956960B2 JP6956960B2 JP2017554194A JP2017554194A JP6956960B2 JP 6956960 B2 JP6956960 B2 JP 6956960B2 JP 2017554194 A JP2017554194 A JP 2017554194A JP 2017554194 A JP2017554194 A JP 2017554194A JP 6956960 B2 JP6956960 B2 JP 6956960B2
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- chloride
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- 239000006096 absorbing agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 p-methoxybenzyl group Chemical group 0.000 claims description 96
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002029 aromatic hydrocarbon 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
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000002904 solvent Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000003054 catalyst Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 14
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000007810 chemical reaction solvent Substances 0.000 description 10
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 238000002189 fluorescence spectrum Methods 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000003849 aromatic solvent Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000003963 dichloro group Chemical group Cl* 0.000 description 5
- 230000026030 halogenation Effects 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 4
- HPQRTCWQTKIRJV-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C=C1)O)N2NN=C3N2C=CC=C3 Chemical compound CC(C)(C)C1=CC(=C(C=C1)O)N2NN=C3N2C=CC=C3 HPQRTCWQTKIRJV-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- 229940011051 isopropyl acetate Drugs 0.000 description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- NBHAHMHUMMWFPJ-UHFFFAOYSA-N 1-bromo-2-phenylmethoxybenzene Chemical compound BrC1=CC=CC=C1OCC1=CC=CC=C1 NBHAHMHUMMWFPJ-UHFFFAOYSA-N 0.000 description 3
- KZHKNVNBJZCORJ-UHFFFAOYSA-N 2-bromo-4-tert-butyl-1-phenylmethoxybenzene Chemical compound BrC1=CC(C(C)(C)C)=CC=C1OCC1=CC=CC=C1 KZHKNVNBJZCORJ-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 229940043232 butyl acetate Drugs 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910000103 lithium hydride Inorganic materials 0.000 description 3
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 229940090181 propyl acetate Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- PKFWMISWHRSGAC-UHFFFAOYSA-N tributyl-(4-phenylphenyl)stannane Chemical compound C1=CC([Sn](CCCC)(CCCC)CCCC)=CC=C1C1=CC=CC=C1 PKFWMISWHRSGAC-UHFFFAOYSA-N 0.000 description 3
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- OIXJMPDGGDWJOG-UHFFFAOYSA-N 1,1,1-trichloro-2-[chloro(2,2,2-trichloroethyl)phosphoryl]ethane Chemical compound ClC(Cl)(Cl)CP(Cl)(=O)CC(Cl)(Cl)Cl OIXJMPDGGDWJOG-UHFFFAOYSA-N 0.000 description 2
- ZJOQIRUTMBJWEB-UHFFFAOYSA-N 1,2-dichloro-N,N,N',N'-tetramethylethane-1,2-diamine nickel Chemical compound [Ni].ClC(C(N(C)C)Cl)N(C)C ZJOQIRUTMBJWEB-UHFFFAOYSA-N 0.000 description 2
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BPDSGGQFORKTMY-UHFFFAOYSA-N tetrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=NN=C21 BPDSGGQFORKTMY-UHFFFAOYSA-N 0.000 description 1
- ZKWLZMIZAHQXMU-UHFFFAOYSA-N tetrazolo[1,5-a]quinolin-9-ol Chemical compound OC=1C=CC=C2C=CC=3N(C=12)N=NN=3 ZKWLZMIZAHQXMU-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- CCHPAGARRYUPQC-UHFFFAOYSA-N tributyl-(4-tert-butylphenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C(C)(C)C)C=C1 CCHPAGARRYUPQC-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1
- CCXTYQMZVYIQRP-UHFFFAOYSA-N tris(3-methoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 CCXTYQMZVYIQRP-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
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- 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
- C09K3/00—Materials not provided for elsewhere
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Description
[式(1)及び(2)中、R1及びR2は、それぞれ独立に、置換基を有していてもよいC6-10芳香族環又はC1-10脂肪族炭化水素基を表す。X1及びX2は、それぞれ独立に、窒素原子、リン原子又はホウ素原子を表す。Y1及びY2は、それぞれ独立に、含窒素複素環を表す。n1及びn2は、それぞれ独立に、1又は2の整数を表す。m1は、0〜3の整数を表す。m2は、0〜4の整数を表す。]
下記式(1)又は(2)で表される化合物は、紫外線吸収剤に用いることができる。化合物(1)、(2)では、ヒドロキシ基が含窒素複素環と炭素数3個以内で結合されており、紫外線を吸収した場合も熱失活し、紫外線吸収能を維持しつつ蛍光を抑制できる。
特に、式(1)で表される化合物は、短波長のUV−C光(波長280nm以下)の吸収能が良好である。
芳香族炭化水素環としては、ベンゼン環、ナフタレン環等が挙げられ、ベンゼン環が好ましい。
芳香族複素環としては、下記式で表される芳香族複素環が挙げられ、中でも、チオフェン環、チアゾール環、ピリジン環、ピロール環、イミダゾール環、フラン環、オキサゾール環等が好ましい。式中、R4は、水素原子、又はC1-4アルキル基を表す。
前記ハロゲン原子としては、フッ素原子、塩素原子、ヨウ素原子、臭素原子が挙げられる。
R3におけるハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられ、好ましくは臭素原子、ヨウ素原子である。
また、R2としては脂肪族炭化水素基が好ましい。
R1及びR2は、ベンゼン環上、ヒドロキシ基のパラ位に置換していることが好ましい。
n1及びn2は、好ましくは2である。
なお下記式において、m10が1以上の場合、R10の少なくとも1つは、ヒドロキシ基に対してパラ位に置換していることが好ましい。m20が1以上の場合、R20の少なくとも1つは、ヒドロキシ基に対してパラ位に置換していることが好ましい。
上記化合物(1)の製造方法の概要は、下記スキームで表される。すなわち、本発明の化合物(1)又は(2)は、化合物(1C)又は化合物(2C)を酸化した後(酸化工程:工程1)、得られた化合物(1B)又は(2B)に、塩基の存在下、アジド化合物を反応させ(環化工程:工程2)、得られた化合物(1A)又は(2A)を脱保護することにより製造することができる(脱保護工程:工程3)。
上記化合物(1C)又は(2C)と、酸化剤とを反応させることにより、化合物(1B)又は(2B)を得ることができる。化合物(1C)又は(2C)としては、それぞれ、例えば、式(1C−I)で表される化合物(1C−I−1)〜(1C−I−25)又は式(2C−I)で表される化合物(2C−I−1)〜(2C−I−25)が好ましい。
酸化工程における反応溶媒としては、ジクロロメタン、クロロホルム、ジクロロエタン、ジクロロプロパン等のハロゲン系溶媒;メタノール、エタノール、n−プロパノール、2−プロパノール、n−ブタノール等のアルコール系溶媒;酢酸、トリフルオロ酢酸等のカルボン酸系溶媒;水;或いはこれらの混合溶媒;が挙げられ、ハロゲン系溶媒が好ましい。
上記化合物(1B)又は(2B)に、塩基の存在下、アジド化合物を反応させることで、化合物(1A)又は(2A)を得ることができる。本工程に用いられる化合物(1B)又は(2B)としては、それぞれ、例えば、式(1B−I)で表される化合物(1B−I−1)〜(1B−I−25)又は式(2B−I)で表される化合物(2B−I−1)〜(2B−I−25)が好ましい。
前記スルホニルハライド化合物としては、メタンスルホニルクロリド、エタンスルホニルクロリド、プロパンスルホニルクロリド、イソプロパンスルホニルクロリド、ブタンスルホニルクロリド、ペンタンスルホニルクロリド、ヘキサンスルホニルクロリド;等のアルキルスルホニルクロリド化合物;ベンゼンスルホニルクロリド、2−メチルベンゼンスルホニルクロリド、3−メチルベンゼンスルホニルクロリド、4−メチルベンゼンスルホニルクロリド、2−クロロベンゼンスルホニルクロリド、3−クロロベンゼンスルホニルクロリド、4−クロロベンゼンスルホニルクロリド、2−ブロモベンゼンスルホニルクロリド、3−ブロモベンゼンスルホニルクロリド、4−ブロモベンゼンスルホニルクロリド、2−ヨードベンゼンスルホニルクロリド、3−ヨードベンゼンスルホニルクロリド、4−ヨードベンゼンスルホニルクロリド、2−フルオロベンゼンスルホニルクロリド、3−フルオロベンゼンスルホニルクロリド、4−フルオロベンゼンスルホニルクロリド、2−トリフルオロメチルベンゼンスルホニルクロリド、3−トリフルオロメチルベンゼンスルホニルクロリド、4−トリフルオロメチルベンゼンスルホニルクロリド等のアリールスルホニルクロリド化合物;塩化スルフリル;等のスルホニルクロリド化合物;ノナフルオロブタンスルホン酸フルオリド、フェニルスルホン酸フルオリド等のスルホニルフルオリド化合物;等が挙げられる。中でも、スルホニルクロリド化合物が好ましく、アリールスルホニルクロリド化合物がより好ましく、4−メチルベンゼンスルホニルクロリドがさらに好ましい。
上記(1A)又は(2A)を脱保護することにより製造することができる(脱保護工程:工程3)。本工程に用いられる化合物(1A)又は(2A)としては、それぞれ、例えば、式(1A−I)で表される化合物(1A−I−1)〜(1A−I−25)又は式(2A−I)で表される化合物(2A−I−1)〜(2A−I−25)が好ましい。
上記化合物(1C)又は(2C)としては、市販品を用いてもよいし、以下の方法により製造してもよい。
化合物(1C)は、例えば、化合物(1G)のヒドロキシ基を保護し(保護工程:工程4)、次いで得られた化合物(1F)をハロゲン化し(ハロゲン化工程:工程5)、さらに得られた化合物(1E)と化合物(1D)とを反応させる(付加工程1:工程6)ことにより得ることができる。
また化合物(2C)は、例えば、化合物(2G)をハロゲン化し(ハロゲン化工程:工程7)、次いで得られた化合物(2F)のヒドロキシ基を保護し(保護工程:工程8)、さらに得られた化合物(2E)と金属マグネシウムを反応させグリニャール試薬とした上で、ニッケル触媒の存在下、化合物(2D)とを反応させる(付加工程2:工程9)ことにより得ることができる。
以下、各工程について説明する。
X11、X21、X22は、それぞれ独立に、ハロゲン原子を表す。
M1は、ホウ素原子又はスズ原子を表す。
L1は、それぞれ独立に、脂肪族炭化水素基、水酸基、アルコキシ基又はアリールオキシ基を表し、複数のL1は、M1とともに環を形成していてもよい。
k1は、2又は3の整数を表す。]
保護工程は、種々の方法により行うことができ、ヒドロキシ基の保護基としてベンジル基を用いる場合は、例えば、化合物(1G)又は化合物(2F)のヒドロキシ基に、塩基の存在下、臭化ベンジルを反応させることにより行うことができる。
前記塩基としては、炭酸カリウム等のアルカリ金属炭酸塩;水酸化ナトリウム等のアルカリ金属水酸化物;を用いることができる。反応溶媒としては、アセトニトリル等のニトリル系溶媒が好ましい。
ハロゲン化は、種々の方法により行うことができ、例えば、化合物(1F)又は化合物(2G)に、酸の共存下、ハロゲン化試薬と接触させることにより行うことができる。前記酸としては、酢酸等の有機酸が好ましく、ハロゲン化試薬としては、N−ブロモスクシンイミド、N−クロロスクシンイミド、N−ヨードスクシンイミド、ピリジン臭素錯体塩、臭素、塩素、よう素等が好ましい。
反応溶媒としては、ジクロロメタン、クロロホルム、ジクロロエタン、ジクロロプロパン等のハロゲン系溶媒、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸イソプロピル、酢酸ブチルなどのエステル系溶媒、ペンタン、ヘキサン、シクロヘキサン、ヘプタンなどの炭化水素系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼンなどの芳香族系溶媒が好ましい。
ハロゲン化により得られた化合物(1E)を下記式で表される化合物(1D)と反応させることにより、化合物(1C)を製造することができる。
k1は、M1の種類に応じて2又は3であり、M1がホウ素原子の場合2であり、M1がスズ原子の場合3である。
中でも、下記式(Om−1)、(Om−2)、(Om−5)、(Om−6)で表される基が好ましい。
これらの中でも、トルエン、キシレン、テトラヒドロフラン、ジオキサン、N,N−ジメチルホルムアミドが特に好ましい。
反応には、マイクロウェーブを使用してもよい。
化合物(2E)と金属マグネシウムを反応させグリニャール試薬とした上で、ニッケル触媒の存在下、化合物(2D)と反応させることにより、化合物(2C)を得ることができる。本工程の原料に用いられる化合物(2E)としては、例えば、式(2E−I)で表される化合物(2E−I−1)〜(2E−I−25)が好ましい。
反応系中、水を含まないことが好ましい。また、還流下で反応を行うことが好ましい。
反応系中、水を含まないことが好ましい。また、還流下で反応を行うことが好ましい。
本発明の紫外線吸収剤と、樹脂とを含有する紫外線吸収剤含有組成物(以下、単に「樹脂組成物」という場合がある)も本発明の範囲に包含される。
また前記樹脂としては、ポリオレフィン系樹脂、ポリエステル系樹脂、ポリスチレン系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、ポリイミド系樹脂、ポリアミドイミド樹脂、フッ素系樹脂、ポリ(メタ)アクリル系樹脂、シリコーン系樹脂、ウレタン系樹脂、セルロール系樹脂、塩化ビニル樹脂、アクリロニトリル−ブタジエン−スチレン共重合合成樹脂等が挙げられる。
各物性の測定方法は、以下の通りである。
熱重量分析装置(島津製作所製、「TGA−50」)を用いて熱重量分析測定を行った。
得られた化合物を0.03g/Lの濃度になるようにクロロホルムに溶解し、紫外・可視分光装置(島津製作所製、「UV−2450」)及び光路長1cmのセルを用いて紫外可視吸収スペクトル測定を行った。
次いで、メタクロロ過安息香酸(mCPBA)(1.5モル当量)及び無水ジクロロメタン20mL)を入れ、室温で24時間撹拌した。反応終了後、精製して9−ベンジルオキシインキノリン−N−オキシド(白色固体)を1.12g得た(収率75%)。
ねじ口試験管に9−ベンジルオキシインキノリン−N−オキシド(1.12g)、ジフェニルホスホリルアジド(DPPA)(5モル当量)及び無水ピリジン(2モル当量)を入れ、窒素雰囲気下、120℃で24時間撹拌した。反応終了後、精製して9−ベンジルオキシテトラゾロ[1,5−a]キノリン(白色固体)を630mg得た(収率51%)。
さらに、50mLフラスコに9−ベンジルオキシテトラゾロ[1,5−a]キノリン(276mg、1mmol)、エタノール(5mL)を入れ、5%パラジウム炭素触媒(50mg)を入れ、さらに水素ガスを導入して、室温で2時間撹拌した。反応終了後、精製し、9−ヒドロキシテトラゾロ[1,5−a]キノリンを102mg得た(収率55%)。
6−ブロモ−9−ベンジルオキシキノリン(630mg、2mmol)、1−tert−ブチル−4−(トリブチルスタンニル)ベンゼン(1.2モル当量)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.1モル当量)及び無水トルエン(5mL)を入れ、マイクロウェーブ反応装置を用いて180℃で10分撹拌した。反応終了後、精製し、6−(4−tert−ブチルフェニル)−9−ベンジルオキシキノリンを780mg得た。
さらに、メタクロロ過安息香酸(mCPBA)(1.5モル当量)及び無水ジクロロメタン(10mL)を入れ、室温で8時間撹拌した。反応終了後、精製して6−(4−tert−ブチルフェニル)−9−ベンジルオキシキノリン−N−オキシドを595mg得た(収率72%)。
ねじ口試験管にジフェニルホスホリルアジド(DPPA)(5モル当量)及び無水ピリジン(2モル当量)を入れ、窒素雰囲気下、120℃で24時間撹拌した。反応液を精製し、6−(4−tert−ブチルフェニル)−9−ベンジルオキシテトラゾロ[1,5−a]キノリンを450mg得た(収率71%)。
さらに100mLフラスコに6−(4−tert−ブチルフェニル)−9−ベンジルオキシテトラゾロ[1,5−a]キノリン(343mg、0.84mmol)、エタノール/酢酸エチル混合溶媒(1:1)(10mL)を入れ、5%パラジウム炭素触媒(50mg)を入れ、さらに水素ガスを導入して、60℃で4時間撹拌した。反応終了後、精製して、6−(4−tert−ブチルフェニル)−9−ヒドロキシテトラゾロ[1,5−a]キノリンを146mg得た(収率55%)。
6−ブロモ−9−ベンジルオキシキノリン(787mg、2.5mmol)、1−フェニル−4−(トリブチルスタンニル)ベンゼン(1.2モル当量)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.1モル当量)及び無水トルエン(5mL)を入れ、マイクロウェーブ反応装置を用いて180℃で10分撹拌した。反応終了後、精製し、6−(4−フェニルフェニル)−9−ベンジルオキシキノリンを320mg得た。
さらに、メタクロロ過安息香酸(mCPBA)(1.5モル当量)及び無水ジクロロメタン(10mL)を入れ、室温で2日間撹拌した。反応終了後、精製して6−(4−フェニルフェニル)−9−ベンジルオキシキノリン−N−オキシドを180mg得た(収率75%)。
ねじ口試験管にジフェニルホスホリルアジド(DPPA)(5モル当量)及び無水ピリジン(2モル当量)を入れ、窒素雰囲気下、120℃で24時間撹拌した。反応液を精製し、6−(4−フェニルフェニル)−9−ベンジルオキシテトラゾロ[1,5−a]キノリンを109mg得た(収率57%)。
さらに6−(4−フェニルフェニル)−9−ベンジルオキシテトラゾロ[1,5−a]キノリン(109mg)と、テトラヒドロフラン(20mL)を100mLフラスコに入れ、5%パラジウム炭素触媒(30mg)を入れ、さらに水素ガスを導入して、60℃で6時間撹拌した。反応終了後、精製して、6−(4−フェニルフェニル)−9−ヒドロキシテトラゾロ[1,5−a]キノリンを65mg得た(収率77%)。
4−(2−ヒドロキシフェニル)−テトラゾロ[1,5−a]ピリジンの合成(実施例4)
3−(2−ヒドロキシ−5−tert−ブチルフェニル)−テトラゾロ[1,5−a]ピリジンの合成(実施例5)
工程(1):2−ブロモ−1−ベンジルオキシベンゼンの合成
次いで、2−ブロモ−1−ヒドロキシ−4−tert−ブチルベンゼン(2.29g、19mmol)、臭化ベンジル(1.2モル当量)、炭酸カリウム(1.5モル当量)、アセトニトリル60mLを加え、還流下、一晩撹拌した。反応終了後、精製し2−ブロモ−1−ベンジルオキシ−4−tert−ブチルベンゼンを4.33g得た。
次いで、メタクロロ過安息香酸(1.5モル当量)及び無水ジクロロメタン(10mL)を入れ、室温で19時間撹拌した。反応終了後、精製して、2−(1−ベンジルオキシフェニル)ピリジン−N−オキシドを790mg(収率79%)又は2−(1−ベンジルオキシ−4−tert−ブチルフェニル)ピリジンを1.87g得た。
ねじ口試験管にジフェニルホスホリルアジド(DPPA)(5モル当量)、無水ピリジン(2モル当量)を入れ、窒素雰囲気下、120℃で24時間撹拌した。反応終了後、精製して、4−(2−ベンジルオキシフェニル)−テトラゾロ[1,5−a]ピリジンを850mg(収率98%)又は3−(2−ベンジルオキシ−5−tert−ブチルフェニル)−テトラゾロ[1,5−a]ピリジンを863mg(収率57%)得た。
さらに50mLフラスコに4−(2−ベンジルオキシフェニル)−テトラゾロ[1,5−a]ピリジン(850mg)又は3−(2−ベンジルオキシ−5−tert−ブチルフェニル)−テトラゾロ[1,5−a]ピリジン(863mg)、エタノール/酢酸エチル混合溶媒(1:1)(30mL)を入れ、5%パラジウム炭素触媒(100mg)を入れ、さらに水素ガスを導入して、60℃で4時間撹拌した。反応終了後、精製して、4−(2−ヒドロキシフェニル)−テトラゾロ[1,5−a]ピリジンを530mg(収率85%)又は3−(2−ヒドロキシ−5−tert−ブチルフェニル)−テトラゾロ[1,5−a]ピリジンを642mg得た(収率99%)。
2−(2−ヒドロキシ−5−tert−ブチルフェニル)ベンゾトリアゾールを比較例の化合物とした。
6−[4−(4’−tert−ブチル)ビフェニル]−9−ヒドロキシテトラゾロ[1,5−a]キノリンの合成
100mLフラスコに9−ベンジルオキシキノリン1.18g(5mmol)、臭素(1モル当量)、無水クロロホルム(10mL)を入れ、室温で17時間撹拌した。次いで、臭素(1モル当量)を追加し、室温でさらに2時間撹拌した。反応終了後、精製し6−ブロモ−9−ベンジルオキシキノリンを1.67g得た。
6−ブロモ−9−ベンジルオキシキノリン(630mg、2.0mmol)、4−tert−ブチル−4’−(トリブチルスタンニル)ビフェニル(1.2モル当量)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.1モル当量)及び無水トルエン(5mL)を入れ、マイクロウェーブ反応装置を用いて180℃で20分撹拌した。反応終了後、精製し、6−[4−(4’−tert−ブチル)ビフェニル]−9−ベンジルオキシキノリンを983mg得た。
さらに、メタクロロ過安息香酸(mCPBA)(1.5モル当量)及び無水ジクロロメタン(10mL)を入れ、室温で12時間撹拌した。反応終了後、精製して6−[4−(4’−tert−ブチル)ビフェニル]−9−ベンジルオキシキノリン−N−オキシドを552mg得た(収率60%)。
ねじ口試験管にジフェニルホスホリルアジド(DPPA)(5モル当量)及び無水ピリジン(2モル当量)を入れ、窒素雰囲気下、120℃で24時間撹拌した。反応液を精製し、6−[4−(4’−tert−ブチル)ビフェニル]−9−ベンジルオキシテトラゾロ[1,5−a]キノリンを121mg得た(収率17%)。
さらに6−[4−(4’−tert−ブチル)ビフェニル]−9−ベンジルオキシテトラゾロ[1,5−a]キノリン(121mg)と、テトラヒドロフラン(20mL)エタノール(10mL)を100mLフラスコに入れ、10%パラジウム炭素触媒(100mg)を入れ、さらに水素ガスを導入して、60℃で2時間撹拌した。反応終了後、精製して、6−[4−(4’−tert−ブチル)ビフェニル]−9−ヒドロキシテトラゾロ[1,5−a]キノリンを91mg得た(収率92%)。
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