JPH0575748B2 - - Google Patents
Info
- Publication number
- JPH0575748B2 JPH0575748B2 JP2544287A JP2544287A JPH0575748B2 JP H0575748 B2 JPH0575748 B2 JP H0575748B2 JP 2544287 A JP2544287 A JP 2544287A JP 2544287 A JP2544287 A JP 2544287A JP H0575748 B2 JPH0575748 B2 JP H0575748B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- synthesis
- yield
- formula
- groups
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 description 85
- 230000015572 biosynthetic process Effects 0.000 description 84
- -1 N-methylacetylaminomethyl group Chemical group 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 239000013078 crystal Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- NZLCEIYRRDWTEV-UHFFFAOYSA-N 5-tert-butyl-1,2-oxazol-3-one Chemical compound CC(C)(C)C1=CC(O)=NO1 NZLCEIYRRDWTEV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical class OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 4
- AFVFIJAYAFTQRB-UHFFFAOYSA-N 5-phenylisoxazol-3-ol Chemical compound O1N=C(O)C=C1C1=CC=CC=C1 AFVFIJAYAFTQRB-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FWPDXKAPOBVGQT-UHFFFAOYSA-N 1-ethyl-5-iodo-2-methyl-4-nitroimidazole Chemical compound CCN1C(C)=NC([N+]([O-])=O)=C1I FWPDXKAPOBVGQT-UHFFFAOYSA-N 0.000 description 3
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical compound OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 description 3
- ATCHDWWVBOYDRW-UHFFFAOYSA-N 5-tert-butylpyrazolidin-3-one Chemical compound CC(C)(C)C1CC(=O)NN1 ATCHDWWVBOYDRW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OHQHYFUBCXVTIW-UHFFFAOYSA-N 1-decylsulfanyl-2-nitro-4-(trifluoromethyl)benzene Chemical compound CCCCCCCCCCSC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O OHQHYFUBCXVTIW-UHFFFAOYSA-N 0.000 description 2
- YXXNVDWHLYGBAB-UHFFFAOYSA-N 1-decylsulfonyl-2-nitro-4-(trifluoromethyl)benzene Chemical compound CCCCCCCCCCS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O YXXNVDWHLYGBAB-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 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
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 2
- JCIPWPZWBYTTSQ-UHFFFAOYSA-N 4-chloro-n-hexadecyl-n-methyl-3-nitrobenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 JCIPWPZWBYTTSQ-UHFFFAOYSA-N 0.000 description 2
- KLPXQLKDOGQNAA-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1,2-oxazol-3-one Chemical compound C1=CC(OC)=CC=C1C1=CC(O)=NO1 KLPXQLKDOGQNAA-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- VUYNTIDSHCJIKF-UHFFFAOYSA-N ethyl 4,4-dimethyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)(C)C VUYNTIDSHCJIKF-UHFFFAOYSA-N 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NAPORKAUKZRITJ-UHFFFAOYSA-N n-[2-decylsulfonyl-5-(trifluoromethyl)phenyl]hydroxylamine Chemical compound CCCCCCCCCCS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1NO NAPORKAUKZRITJ-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YQQBYLLBRXHRHO-UHFFFAOYSA-M 1-(2-ethylhexyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCC(CC)C[N+]1=CC=CC=C1 YQQBYLLBRXHRHO-UHFFFAOYSA-M 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- UKDQQMUWOMVLCG-UHFFFAOYSA-N 1-chloro-2,4-bis(methylsulfonyl)benzene Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(S(C)(=O)=O)=C1 UKDQQMUWOMVLCG-UHFFFAOYSA-N 0.000 description 1
- UNCOBOZHCCCMCQ-UHFFFAOYSA-N 1-chloro-4-methylsulfonyl-2-tetradecylsulfonylbenzene Chemical compound CCCCCCCCCCCCCCS(=O)(=O)C1=CC(S(C)(=O)=O)=CC=C1Cl UNCOBOZHCCCMCQ-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- PQSXVOZZXRVBGC-UHFFFAOYSA-N 4,4-dibromo-5-tert-butylpyrazolidin-3-one Chemical compound CC(C)(C)C1NNC(=O)C1(Br)Br PQSXVOZZXRVBGC-UHFFFAOYSA-N 0.000 description 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 1
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 1
- SPZGXONNVLTQDE-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 SPZGXONNVLTQDE-UHFFFAOYSA-N 0.000 description 1
- MHSWRIORWSKGGD-UHFFFAOYSA-N 4-chloro-n-hexadecyl-3-nitrobenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCNS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 MHSWRIORWSKGGD-UHFFFAOYSA-N 0.000 description 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 description 1
- BXQDLEHCXQQSCH-UHFFFAOYSA-N 5-phenyl-1,2-oxazole Chemical compound O1N=CC=C1C1=CC=CC=C1 BXQDLEHCXQQSCH-UHFFFAOYSA-N 0.000 description 1
- IQUFYHXKYDGMDZ-UHFFFAOYSA-N 5-tert-butyl-2-[2-decylsulfonyl-5-(trifluoromethyl)phenyl]-1,2-oxazol-3-one Chemical compound CCCCCCCCCCS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1N1C(=O)C=C(C(C)(C)C)O1 IQUFYHXKYDGMDZ-UHFFFAOYSA-N 0.000 description 1
- CCWUPRCJJSLLPA-UHFFFAOYSA-N 5-tert-butyl-2-[2-nitro-4-(trifluoromethyl)phenyl]-1,2-oxazol-3-one Chemical compound O1C(C(C)(C)C)=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O CCWUPRCJJSLLPA-UHFFFAOYSA-N 0.000 description 1
- XRUOLHSSROFHQD-UHFFFAOYSA-N 5-tert-butyl-2-[4-nitro-3-(trifluoromethyl)phenyl]-1,2-oxazol-3-one Chemical compound O1C(C(C)(C)C)=CC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XRUOLHSSROFHQD-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- USKKBCXXAHKNLB-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)N Chemical compound C(CCCCCCCCCCCCCCC)C1=C(C=CC=C1)S(=O)(=O)N USKKBCXXAHKNLB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- JMSIATBGUPSKLE-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)C=1C(NOC=1)=O Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C=1C(NOC=1)=O JMSIATBGUPSKLE-UHFFFAOYSA-N 0.000 description 1
- AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 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
- 150000004725 beta keto acid derivatives Chemical class 0.000 description 1
- 238000007664 blowing Methods 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
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- JAYVCXPSMRJAIH-UHFFFAOYSA-N ethyl 4-chloro-2-hexadecoxy-5-nitrobenzoate Chemical compound CCCCCCCCCCCCCCCCOC1=CC(Cl)=C([N+]([O-])=O)C=C1C(=O)OCC JAYVCXPSMRJAIH-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- LOEIXPJQKVLCSA-UHFFFAOYSA-M potassium;4-chloro-3-nitrobenzenesulfonate Chemical compound [K+].[O-][N+](=O)C1=CC(S([O-])(=O)=O)=CC=C1Cl LOEIXPJQKVLCSA-UHFFFAOYSA-M 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YRQMBQUMJFVZLF-UHFFFAOYSA-N tert-butyl n-(4-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(O)C=C1 YRQMBQUMJFVZLF-UHFFFAOYSA-N 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
ïŒçºæã®åéïŒ
æ¬çºæã¯ïŒâã¢ãªãŒã«ã€ãœãªããµãŸãã³âïŒâ
ãªã³èªå°äœã«é¢ãããã®ã§ããã ïŒåŸæ¥ã®æè¡ïŒ ïŒâã¢ãªãŒã«ã€ãœãªããµãŸãªã³âïŒâãªã³èªå°
äœãšããŠã¯ããããŸã§ã«ãããããµã€ã¯ã«ãº
ïŒHeterocyclesïŒïŒ20(6)ã1123ã1126é ïŒ1983ïŒïŒ
ã±ãã«ã«ã»ã¢ã³ãã»ãã¢ãŒãã»ã³ãã€ã«ã«ã»ãã©
ãã³ïŒChemical amd Pharmaceutical
BulletinïŒïŒ30(9)ã3097â3105é ïŒããããµã€ã¯
ã«ãºïŒ19(3)ïŒ515ã520é ïŒããããµã€ã¯ã«ãºïŒ19
(3)ïŒ521ã524é ïŒãžã€ãŒãã«ã»ãªãã»ã¶ã»ããã
ãµã€ã¯ãªãã¯ã»ã±ãã¹ããªãŒïŒJournal of
Heterocyclic ChemistryïŒïŒ17(4)ïŒ727ã731é ïŒ
ã±ãã«ã«ã»ã¢ã³ãã»ãã¢ãŒãã»ã³ãã€ã«ã« ãã©
ãã³ïŒ19(7)ïŒ1389ã1394é ïŒç¹éæ55â104274
å·ãã±ãã«ã«ã»ã¢ãã¹ãã©ã¯ãèªïŒïŒChemical
AbstroctsïŒã74å·»17å·ïŒ87947PïŒåèªïŒ75å·»23
å·ïŒ140824VïŒåèªïŒ76å·»23å·ïŒ140775aïŒåèªïŒ
97å·»19å·ïŒ162961uçã«ãã®äŸåã³åææ³ãèšèŒ
ãããŠããããïŒäœã®çœ®æåºãã¯ãã«åºãè¶ ãã
é»ååžåŒæ§ã®åºãçµåããã¢ãªãŒã«åºã®ãã®ã¯ãŸ
ã€ããç¥ãããŠããªãã ïŒçºæã®ç®çïŒ æ¬çºæã®ç®çã¯ãïŒäœã®ã¢ãªãŒã«åºã«ã¯ãã«åº
ãè¶ ããé»ååžåŒæ§ã®åºãçµåããïŒâã¢ãªãŒã«
ã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœãæäŸããã
ãšã§ããã ïŒçºæã®æ§æïŒ æ¬çºæã®ååç©ã¯åŒããã§è¡šããããã åŒãã
ãªã³èªå°äœã«é¢ãããã®ã§ããã ïŒåŸæ¥ã®æè¡ïŒ ïŒâã¢ãªãŒã«ã€ãœãªããµãŸãªã³âïŒâãªã³èªå°
äœãšããŠã¯ããããŸã§ã«ãããããµã€ã¯ã«ãº
ïŒHeterocyclesïŒïŒ20(6)ã1123ã1126é ïŒ1983ïŒïŒ
ã±ãã«ã«ã»ã¢ã³ãã»ãã¢ãŒãã»ã³ãã€ã«ã«ã»ãã©
ãã³ïŒChemical amd Pharmaceutical
BulletinïŒïŒ30(9)ã3097â3105é ïŒããããµã€ã¯
ã«ãºïŒ19(3)ïŒ515ã520é ïŒããããµã€ã¯ã«ãºïŒ19
(3)ïŒ521ã524é ïŒãžã€ãŒãã«ã»ãªãã»ã¶ã»ããã
ãµã€ã¯ãªãã¯ã»ã±ãã¹ããªãŒïŒJournal of
Heterocyclic ChemistryïŒïŒ17(4)ïŒ727ã731é ïŒ
ã±ãã«ã«ã»ã¢ã³ãã»ãã¢ãŒãã»ã³ãã€ã«ã« ãã©
ãã³ïŒ19(7)ïŒ1389ã1394é ïŒç¹éæ55â104274
å·ãã±ãã«ã«ã»ã¢ãã¹ãã©ã¯ãèªïŒïŒChemical
AbstroctsïŒã74å·»17å·ïŒ87947PïŒåèªïŒ75å·»23
å·ïŒ140824VïŒåèªïŒ76å·»23å·ïŒ140775aïŒåèªïŒ
97å·»19å·ïŒ162961uçã«ãã®äŸåã³åææ³ãèšèŒ
ãããŠããããïŒäœã®çœ®æåºãã¯ãã«åºãè¶ ãã
é»ååžåŒæ§ã®åºãçµåããã¢ãªãŒã«åºã®ãã®ã¯ãŸ
ã€ããç¥ãããŠããªãã ïŒçºæã®ç®çïŒ æ¬çºæã®ç®çã¯ãïŒäœã®ã¢ãªãŒã«åºã«ã¯ãã«åº
ãè¶ ããé»ååžåŒæ§ã®åºãçµåããïŒâã¢ãªãŒã«
ã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœãæäŸããã
ãšã§ããã ïŒçºæã®æ§æïŒ æ¬çºæã®ååç©ã¯åŒããã§è¡šããããã åŒãã
ãåŒã
åŒäžãR1ã¯ã¢ã«ãã«åºïŒçœ®æåºãæã€ãã®ã
å«ããäŸãã°ã¡ãã«åºããšãã«åºãã€ãœãããã«
åºãã·ã¯ãããã·ã«åºãïœâããã«åºãã¯ãã«ã¡
ãã«åºãâã¡ãã«ã¢ã»ãã«ã¢ããã¡ãã«åºããª
ã¯ãã«ããªã¡ãã«åºãã¢ããã³ãã«åºããŠã³ãã·
ã«åºãããã¿ãã·ã«åºãªã©ïŒããããã¯ã¢ãªãŒã«
åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ãããšãã«
åºãïŒâã¡ãã«ããšãã«åºãïŒâã¡ãã«ããšãã«
åºãïŒâã¡ããã·ããšãã«åºãïŒâã¡ããã·âïŒ
âã¢ã»ã¿ããããšãã«åºãïŒâããã·ã«ãªãã·ã
ãšãã«åºãïŒâãªã¯ã¿ãã·ã«ãªãã·ããšãã«åºã
ïŒâã¹ã«ãâïŒâã¡ããã·ããšãã«åºãªã©ïŒã§ã
ããã¢ã«ãã«åºã®å Žåã«ã¯ïŒãïŒãã¢ãªãŒã«åºã®
å Žåã«ã¯ïŒã24ã®ççŽ æ°ã®ãã®ã奜ãŸããã R2ãR3ãR4ã¯ã¢ã«ã³ãã·åºïŒçœ®æåºãæã€ã
ã®ãå«ããäŸãã°ãã¡ããã·åºãïŒâã¡ããã·ãš
ããã·åºãããšããã·åºãïŒâïœâãããµãã·ã«
ã«ã«ãã¢ã€ã«ããšããã·åºããšããã·åºãïœâã
ãã·ã«ãªãã·åºãïœâãããµãã·ã«ãªãã·åºãã¡
ããã·ãããã«åºãªã©ïŒãã¢ã·ã«åºïŒçœ®æåºãæ
ã€ãã®ãå«ããäŸãã°ã¢ã»ãã«åºãïœâããã«ã
ã€ã«åºããã³ãŸã€ã«åºãïŒâãšããã·ã«ã«ããã«
ãã³ãŸã€ã«åºãïŒïŒïŒâãžã¡ãã«ããããã€ã«åº
ãªã©ïŒãã¢ã«ã³ãã·ãŸãã¯ã¢ãªãŒã«ãªãã·ã«ã«ã
ãã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ã¡ãã
ã·ã«ã«ããã«åºããšããã·ã«ã«ããã«åºãïœâãª
ã¯ãã«ãªãã·ã«ã«ããã«åºãïœâãããµãã·ã«ãª
ãã·ã«ã«ããã«åºãããšããã·ã«ã«ããã«åºãª
ã©ïŒãã¹ã«ããã«åºïŒçœ®æåºãæã€ãã®ãå«ãã
äŸãã°ãã¡ãã«ã¹ã«ããã«åºãã¯ãã«ã¡ãã«ã¹ã«
ããã«åºããšãã«ã¹ã«ããã«åºãïœâããã·ã«ã¹
ã«ããã«åºãïœâããã©ãã·ã«ã¹ã«ããã«åºãã
ãšãã«ã¹ã«ããã«åºãïŒâã¡ãã«ããšãã«ã¹ã«ã
ãã«åºãïœâããã·ã«ã¹ã«ããã«åºãªã©ïŒãã«ã«
ãã€ã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ãã«
ã«ãã¢ã€ã«åºããžã¡ãã«ã«ã«ãã¢ã€ã«åºããžãšã
ã«ã«ã«ãã¢ã€ã«åºãïœâããã«ã«ã«ãã¢ã€ã«åºã
ïŒâïŒïŒïŒïŒâãžâïœâãã³ãã«ããšããã·ïŒã
ããã«ã«ã«ãã¢ã€ã«åºãâã¡ãã«ââïœâãª
ã¯ãã«ã«ã«ãã¢ã€ã«åºãïŒïŒâãããµãã·ã«ã¹ã«
ãã¢ã¢ã€ã«ïŒããšãã«ã«ã«ãã¢ã€ã«åºãâã¡ã
ã«ââïœâãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«åºãïœâ
ãããµãã·ã«ã«ã«ãã¢ã€ã«åºãïŒâïœâããã·ã«
ãªãã·ãããã«ã«ã«ãã¢ã€ã«åºããªã©ïŒãã¹ã«ã
ã¢ã¢ã€ã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ã
ã¡ãã«ã¹ã«ãã¢ã¢ã€ã«åºããžã¡ãã«ã¹ã«ãã¢ã¢ã€
ã«åºããžãšãã«ã¹ã«ãã¢ã¢ã€ã«åºããžããã«ã¹ã«
ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâããã·ã«ã¹
ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâãªã¯ãã«
ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâãããµ
ãã·ã«ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâ
ãªã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«åºãïœâããã·ã«ã¹
ã«ãã¢ã¢ã€ã«åºãâããšãã«ââãããµãã·
ã«ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïŒâã¡ã
ãã·ãããã«ã¹ã«ãã¢ã¢ã€ã«åºããã¹ïŒïŒâã¡ã
ãã·ãšãã«ïŒã¹ã«ãã¢ã¢ã€ã«åºãªã©ïŒããããåºã
ã·ã¢ãåºãããã²ã³ååãŸãã¯ããªãã«ãªãã¡ã
ã«åºã®äžããéžã°ããåºã§ãããR2ããã³R3ã¯
å°ãªããšãäžæ¹ããããåºãã·ã¢ãåºãã¹ã«ãã
ã«åºãŸãã¯ããªãã«ãªãã¡ãã«ããéžã°ããã
R2ãR3ã¯å¥œãŸããã¯å°ãªããšãäžæ¹ã¯ãããåº
ãããã¯ã¹ã«ããã«åºã§ãããç¹ã«R2ãR3ã®å°
ãªããšãäžæ¹ããããåºã§ãããã®ã奜ãŸããã ãã®æR2ãR3ã®ãããåºä»¥å€ã®äžæ¹ã®åºãã
ã³ïŒãŸãã¯R4ãã¹ã«ããã«åºãã¹ã«ãã¢ã¢ã€ã«
åºãã¢ã«ã³ãã·ã«ã«ããã«åºãã«ã«ãã¢ã€ã«åºã
ã¢ã·ã«åºãããªãã«ãªãã¡ãã«åºåã¯ã·ã¢ãåºã§
ãããã®ã奜ãŸããã ç¹ã«ãR2ããããåºã§ãããR3ãã¹ã«ãã¢ã¢
ã€ã«åºãã«ã«ãã¢ã€ã«åºãã¢ã«ã³ãã·ã«ã«ããã«
åºãŸãã¯ããªãã«ãªãã¡ãã«åºã§ãããR4ãæ°Ž
çŽ ååã§ãããã®ã奜ãŸããã æ¬çºæã®ååç©ã¯ãäžè¬ã«ä»¥äžã«èšãããã«å€§
å¥ããŠãããããã¯ããã®äºéãã®æ¹æ³ã§å
æããããšãåºæ¥ãã ãAã çªçŽ â眮æããããã·ã«ã¢ãã³ãããããª
ãŒã«é žèªå°äœïŒãšã¹ãã«ãé žãã©ã€ãïŒã§ïŒ®â
ã¢ã·ã«åããå¡©åºæ§æ¡ä»¶äžãéç°ãïŒâã€ãœãª
ããµãŸãªã³âïŒâãªã³èªå°äœãåŸãæ¹æ³
ïŒChemical AbstractsïŒ76å·»23å·ïŒ140775aïŒ
Chemical AbstractsïŒ75å·»17å·ïŒ110227kãªã©
ã«äŸãç¥ãããŠãããïŒãããã¯çªçŽ â眮æã
ãããã·ã«ã¢ãã³ããžã±ãã³ãããã¯Î²âã±ã
é žèªå°äœã«ããâã¢ã·ã«åãè¡ãªããè±æ°Žé
ç°ãè¡ãªãïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èª
å°äœãåŸãæ¹æ³ïŒHeterocyclesïŒ20å·»ïŒå·ïŒ
1123ã1126é ãå19å·»ïŒå·ïŒ521ã524é ãªã©ã«
äŸãç¥ãããŠãããïŒ ãBã ïŒäœãããã¯ãã®å ±åœ¹äœçœ®ã«é»ååžåŒæ§åº
ãæãããããã³ãŒã³é¡ãªã©ã®ãè³éŠææ±æ žçœ®
æã«å¯ŸããŠæŽ»æ§ãªè³éŠæååç©ãšïŒâãããã
ã·ã€ãœãªããµãŸãŒã«ããžã¡ãã«ã¹ã«ããã·ãã
ããã¯ãžã¡ãã«ãã«ã ã¢ãããªã©ã®éãããã³
æ§æ¥µæ§æº¶åªäžãå¡©åºæ§æ¡ä»¶äžçœ®æåå¿ãè¡ãªã
ïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœãåŸã
æ¹æ³ã§ããã 以äžã«æ¬çºæã®ååç©ã®å ·äœäŸããã®è£œé ã«é©
ããåææ¹æ³ãšãšãã«åæãããäœããæ¬çºæã¯
ãããã®å ·äœäŸã«éå®ããããã®ã§ã¯ãªãã
å«ããäŸãã°ã¡ãã«åºããšãã«åºãã€ãœãããã«
åºãã·ã¯ãããã·ã«åºãïœâããã«åºãã¯ãã«ã¡
ãã«åºãâã¡ãã«ã¢ã»ãã«ã¢ããã¡ãã«åºããª
ã¯ãã«ããªã¡ãã«åºãã¢ããã³ãã«åºããŠã³ãã·
ã«åºãããã¿ãã·ã«åºãªã©ïŒããããã¯ã¢ãªãŒã«
åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ãããšãã«
åºãïŒâã¡ãã«ããšãã«åºãïŒâã¡ãã«ããšãã«
åºãïŒâã¡ããã·ããšãã«åºãïŒâã¡ããã·âïŒ
âã¢ã»ã¿ããããšãã«åºãïŒâããã·ã«ãªãã·ã
ãšãã«åºãïŒâãªã¯ã¿ãã·ã«ãªãã·ããšãã«åºã
ïŒâã¹ã«ãâïŒâã¡ããã·ããšãã«åºãªã©ïŒã§ã
ããã¢ã«ãã«åºã®å Žåã«ã¯ïŒãïŒãã¢ãªãŒã«åºã®
å Žåã«ã¯ïŒã24ã®ççŽ æ°ã®ãã®ã奜ãŸããã R2ãR3ãR4ã¯ã¢ã«ã³ãã·åºïŒçœ®æåºãæã€ã
ã®ãå«ããäŸãã°ãã¡ããã·åºãïŒâã¡ããã·ãš
ããã·åºãããšããã·åºãïŒâïœâãããµãã·ã«
ã«ã«ãã¢ã€ã«ããšããã·åºããšããã·åºãïœâã
ãã·ã«ãªãã·åºãïœâãããµãã·ã«ãªãã·åºãã¡
ããã·ãããã«åºãªã©ïŒãã¢ã·ã«åºïŒçœ®æåºãæ
ã€ãã®ãå«ããäŸãã°ã¢ã»ãã«åºãïœâããã«ã
ã€ã«åºããã³ãŸã€ã«åºãïŒâãšããã·ã«ã«ããã«
ãã³ãŸã€ã«åºãïŒïŒïŒâãžã¡ãã«ããããã€ã«åº
ãªã©ïŒãã¢ã«ã³ãã·ãŸãã¯ã¢ãªãŒã«ãªãã·ã«ã«ã
ãã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ã¡ãã
ã·ã«ã«ããã«åºããšããã·ã«ã«ããã«åºãïœâãª
ã¯ãã«ãªãã·ã«ã«ããã«åºãïœâãããµãã·ã«ãª
ãã·ã«ã«ããã«åºãããšããã·ã«ã«ããã«åºãª
ã©ïŒãã¹ã«ããã«åºïŒçœ®æåºãæã€ãã®ãå«ãã
äŸãã°ãã¡ãã«ã¹ã«ããã«åºãã¯ãã«ã¡ãã«ã¹ã«
ããã«åºããšãã«ã¹ã«ããã«åºãïœâããã·ã«ã¹
ã«ããã«åºãïœâããã©ãã·ã«ã¹ã«ããã«åºãã
ãšãã«ã¹ã«ããã«åºãïŒâã¡ãã«ããšãã«ã¹ã«ã
ãã«åºãïœâããã·ã«ã¹ã«ããã«åºãªã©ïŒãã«ã«
ãã€ã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ãã«
ã«ãã¢ã€ã«åºããžã¡ãã«ã«ã«ãã¢ã€ã«åºããžãšã
ã«ã«ã«ãã¢ã€ã«åºãïœâããã«ã«ã«ãã¢ã€ã«åºã
ïŒâïŒïŒïŒïŒâãžâïœâãã³ãã«ããšããã·ïŒã
ããã«ã«ã«ãã¢ã€ã«åºãâã¡ãã«ââïœâãª
ã¯ãã«ã«ã«ãã¢ã€ã«åºãïŒïŒâãããµãã·ã«ã¹ã«
ãã¢ã¢ã€ã«ïŒããšãã«ã«ã«ãã¢ã€ã«åºãâã¡ã
ã«ââïœâãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«åºãïœâ
ãããµãã·ã«ã«ã«ãã¢ã€ã«åºãïŒâïœâããã·ã«
ãªãã·ãããã«ã«ã«ãã¢ã€ã«åºããªã©ïŒãã¹ã«ã
ã¢ã¢ã€ã«åºïŒçœ®æåºãæã€ãã®ãå«ããäŸãã°ã
ã¡ãã«ã¹ã«ãã¢ã¢ã€ã«åºããžã¡ãã«ã¹ã«ãã¢ã¢ã€
ã«åºããžãšãã«ã¹ã«ãã¢ã¢ã€ã«åºããžããã«ã¹ã«
ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâããã·ã«ã¹
ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâãªã¯ãã«
ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâãããµ
ãã·ã«ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïœâ
ãªã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«åºãïœâããã·ã«ã¹
ã«ãã¢ã¢ã€ã«åºãâããšãã«ââãããµãã·
ã«ã¹ã«ãã¢ã¢ã€ã«åºãâã¡ãã«ââïŒâã¡ã
ãã·ãããã«ã¹ã«ãã¢ã¢ã€ã«åºããã¹ïŒïŒâã¡ã
ãã·ãšãã«ïŒã¹ã«ãã¢ã¢ã€ã«åºãªã©ïŒããããåºã
ã·ã¢ãåºãããã²ã³ååãŸãã¯ããªãã«ãªãã¡ã
ã«åºã®äžããéžã°ããåºã§ãããR2ããã³R3ã¯
å°ãªããšãäžæ¹ããããåºãã·ã¢ãåºãã¹ã«ãã
ã«åºãŸãã¯ããªãã«ãªãã¡ãã«ããéžã°ããã
R2ãR3ã¯å¥œãŸããã¯å°ãªããšãäžæ¹ã¯ãããåº
ãããã¯ã¹ã«ããã«åºã§ãããç¹ã«R2ãR3ã®å°
ãªããšãäžæ¹ããããåºã§ãããã®ã奜ãŸããã ãã®æR2ãR3ã®ãããåºä»¥å€ã®äžæ¹ã®åºãã
ã³ïŒãŸãã¯R4ãã¹ã«ããã«åºãã¹ã«ãã¢ã¢ã€ã«
åºãã¢ã«ã³ãã·ã«ã«ããã«åºãã«ã«ãã¢ã€ã«åºã
ã¢ã·ã«åºãããªãã«ãªãã¡ãã«åºåã¯ã·ã¢ãåºã§
ãããã®ã奜ãŸããã ç¹ã«ãR2ããããåºã§ãããR3ãã¹ã«ãã¢ã¢
ã€ã«åºãã«ã«ãã¢ã€ã«åºãã¢ã«ã³ãã·ã«ã«ããã«
åºãŸãã¯ããªãã«ãªãã¡ãã«åºã§ãããR4ãæ°Ž
çŽ ååã§ãããã®ã奜ãŸããã æ¬çºæã®ååç©ã¯ãäžè¬ã«ä»¥äžã«èšãããã«å€§
å¥ããŠãããããã¯ããã®äºéãã®æ¹æ³ã§å
æããããšãåºæ¥ãã ãAã çªçŽ â眮æããããã·ã«ã¢ãã³ãããããª
ãŒã«é žèªå°äœïŒãšã¹ãã«ãé žãã©ã€ãïŒã§ïŒ®â
ã¢ã·ã«åããå¡©åºæ§æ¡ä»¶äžãéç°ãïŒâã€ãœãª
ããµãŸãªã³âïŒâãªã³èªå°äœãåŸãæ¹æ³
ïŒChemical AbstractsïŒ76å·»23å·ïŒ140775aïŒ
Chemical AbstractsïŒ75å·»17å·ïŒ110227kãªã©
ã«äŸãç¥ãããŠãããïŒãããã¯çªçŽ â眮æã
ãããã·ã«ã¢ãã³ããžã±ãã³ãããã¯Î²âã±ã
é žèªå°äœã«ããâã¢ã·ã«åãè¡ãªããè±æ°Žé
ç°ãè¡ãªãïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èª
å°äœãåŸãæ¹æ³ïŒHeterocyclesïŒ20å·»ïŒå·ïŒ
1123ã1126é ãå19å·»ïŒå·ïŒ521ã524é ãªã©ã«
äŸãç¥ãããŠãããïŒ ãBã ïŒäœãããã¯ãã®å ±åœ¹äœçœ®ã«é»ååžåŒæ§åº
ãæãããããã³ãŒã³é¡ãªã©ã®ãè³éŠææ±æ žçœ®
æã«å¯ŸããŠæŽ»æ§ãªè³éŠæååç©ãšïŒâãããã
ã·ã€ãœãªããµãŸãŒã«ããžã¡ãã«ã¹ã«ããã·ãã
ããã¯ãžã¡ãã«ãã«ã ã¢ãããªã©ã®éãããã³
æ§æ¥µæ§æº¶åªäžãå¡©åºæ§æ¡ä»¶äžçœ®æåå¿ãè¡ãªã
ïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœãåŸã
æ¹æ³ã§ããã 以äžã«æ¬çºæã®ååç©ã®å ·äœäŸããã®è£œé ã«é©
ããåææ¹æ³ãšãšãã«åæãããäœããæ¬çºæã¯
ãããã®å ·äœäŸã«éå®ããããã®ã§ã¯ãªãã
ãåã
ãåã
ãåã
ãåã
ãåã
ãåã
ãåã
ãåã
ïŒçºæã®å¹æïŒ
æ¬çºæã®ååç©ã¯ããã²ã³åéåçæå
ææã®
åéã«ãããŠãããžäœçšååç©ãšåŒã°ãããé žå
éå åå¿ãè¡ãªãåççã«æçšãªè©Šè¬ãæŸåºãã
ååç©çŸ€ã®äžã§ããšãããéèŠãªäžçŸ€ã®ååç©ã
åæããããã®éèŠäžéäœã§ããã æ¬çºæã®ååç©ãäžéäœãšããããžäœçšååç©
ã¯äŸãã°ãç¹é¡æ60â244873å·ãç¹é¡æ61â
88625å·ãç¹é¡æ61â88623å·ãç¹é¡æ61â89502
å·ãç¹é¡æ61â130342å·ãç¹é¡æ61â136947å·ã«
èšèŒãããŠãããšãããå€ãã®æçšæ§ãæããŠã
ãããŸããïŒâã¢ãªãŒã«âïŒâã€ãœãªããµãŸãªã³
âïŒâãªã³èªå°äœã¯é€èå€ã殺èå€ãé®çå€ãæ¶
çå€ãªã©ãšããŠã®è¬çäœçšãæããŠããçç掻æ§
ç©è³ªãšããŠãéèŠãªæå³ãæããŠããã 以äžã«å®æœäŸãæ²ããæ¬çºæãæŽã«è©³çŽ°ã«èª¬æ
ããã å®æœäŸ ïŒ åææ³ããã«ããååç©äŸããïŒâïœâããã«
âïŒâïŒïŒâããã·ã«ã¹ã«ããã«âïŒâããªãã«
ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãªã³â
ïŒâãªã³ã®åæã åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâãã©ãŸãªãã³ã®åæ 1.0Kgã®ãããã€ã«é ¢é žãšãã«ã2.5ã®ãšã¿ã
ãŒã«ã«æº¶è§£ããæ°Žå·äž320ïœã®å æ°Žããã©ãžã³ã
滎äžããã滎äžçµäºåŸã宀枩ã«ãŠäžæ©åå¿ããã®
ã¡5.0ã®æ°Žãæ·»å ãæ¹æãããæåºããçµæ¶ã
æžå§ãéããæ°Žã§è¯ãæŽæµããã®ã¡å°éã®ã¡ã¿ã
ãŒã«ã§æŽã颚也ãããåé812ïœãåç98.5ïŒ ã åæäŸ ïŒâïŒïŒïŒïŒâãžããã âïŒâïœâãã
ã«âïŒâãã©ãŸãªãã³ã®åæ ïŒâïœâããã«âïŒâãã©ãŸãªãã³658ïœã2.0
ã®é ¢é žã«æº¶è§£ãããæ°Žå·äžãæ¹æããªãããã®
溶液ã«èçŽ 1.5Kgã滎äžããã滎äžçµäºåŸãäžæ©
åå¿ããã®ã¡5.0ã®æ°Žãæ·»å ãããæåºããçµ
æ¶ãæžå§ãéããæ°Žã§è¯ãæŽæµããã®ã¡å°éã®ã¡
ã¿ããŒã«ã§æŽã颚也ãããåé1.36Kgãåç97.2
ïŒ ã åæäŸ ïŒâïŒ ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«é žã®åæ 552ïœã®æ°Žé žåãããªãŠã ã3.0ã®æ°Žã«æº¶è§£
ããæ°·ãå ããŠïŒâ以äžãšãããã€ãã§æ¹æããª
ããããžããã âïŒâïœâããã«âïŒâãã©ãŸãª
ãã³ãïŒâ以äžã«ä¿ã¡ãªããå°éãã€æ·»å ããã
枩床ãäžæããå Žåã«ã¯æ°·ã®çºæ³¡ãé²ãããã«ã¢
ã»ããããªã«ãæ·»å ãããåå¿çµäºåŸã6Nå¡©é ž
ã§é žæ§ãšããã®ã¡é ¢é žãšãã«ãå ãïŒåºŠæœåºã
ãã æœåºæ¶²ã¯ç¡æ°Žç¡«é žãããªãŠã ã§ä¹Ÿç¥ããåŸãé ¢
é žãšãã«ãæžå§çå»ãããæ®æž£ã®ãªã€ã«ãïŒïŒïŒ
âãžã¡ãã«âïŒâãã³ããªãŒã«é žã§ãã€ãããã®
ãªã€ã«ã¯ç²Ÿè£œãã次ã®åå¿ã«çšããã åæäŸ ïŒâïŒ ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«é žã¯ããª
ãã®åæ 466ïœã®ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«
é žã3.5ã®å¡©åã¡ãã¬ã³ã«æ··åããæ¹æããã
ããã«483ïœã®å¡©åããªãã«ãå ãïŒæéåå¿åŸã
å ç±éæµãããšæ¿ããå¡©åæ°ŽçŽ ã¬ã¹ãçºçããã
ïŒæéå ç±éæµããã®ã¡ã溶åªãçå»ãæžå§èžç
ãè¡ãªã€ããç®çç©ã¯ç¡è²ã®æ¶²äœã§ãbp.20çŽ70
âã§ãã€ããåé290ïœãåç54.3ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ããªâïŒâããããã³ãŸããªãã«ãª
ãªãã®åæ 56.4ïœã®ïŒâã¯ããâïŒâããããã³ãŸããªã
ã«ãªãªãã44ïœã®ãã·ã«ã¡ã«ã«ãã¿ã³ã50ïœã®ã
ããªãŠã ã¡ããã·ãã300mlã®ã¡ã¿ããŒã«ãæ··å
ãã80âïŒæéåå¿ãããå·åŽåŸæ°·æ°Žã«æ³šãæåº
ããçµæ¶ããåãããåé88.0ïœãåçã96.9
ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã³ãŸããª
ãã«ãªãªãã®åæ 86ïœã®ïŒâãã·ã«ããªâïŒâããããã³ãŸããª
ãã«ãªãªãã300mlã®é ¢é žãæ··åããïŒïœã®ã¿ã³
ã°ã¹ãã³é žãããªãŠã ãå ãã70âã«å ç±ããã
ããã«35ïŒ éé žåæ°ŽçŽ æ°Ž46mlã80ã85âã«ä¿ã¡ãª
ãã滎äžããã滎äžçµäºåŸããã®æž©åºŠã§ïŒæéå
å¿ãããåå¿åŸãæ°Žã«æ³šãæåºããçµæ¶ããåã
也ç¥ãããåé93.1ïœãåç99.3ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã·ã¢ãã
ãã³ãŸããªãã«ãªãªãã®åæ 100ïœã®ïŒâãã·ã«ã¹ã«ããã«âïŒâãããã
ã³ãŸããªãã«ãªãªãã100ïœã®äºéç²æ«ã450mlã®
ãšã¿ããŒã«ãæ··åãã50ã65âã«ä¿ã¡ãªãã10ïŒ
å¡©åã¢ã³ã¢ããŠã 氎溶液ã滎äžãããåå¿çµäº
åŸãã»ã©ã€ãããããŠããéãè¡ãªãäžæº¶ç©ãé€
å»ããã®ã¡ãæ°Žã«æ³šããé ¢é žãšãã«ã§æœåºããã
溶åªãçå»åŸïœâãããµã³ããåçµæ¶ãããåé
80.2ïœãåç84ïŒ åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒâãã·ã«ã¹ã«ããã«
âïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€
ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 10ïœã®ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã·
ã¢ãããã³ãŸããªãã«ãªãªããš4.2ïœã®ïŒïŒïŒâ
ãžã¡ãã«ãã³ããªãŒã«é žã¯ããªãã80mlã®ãšãŒã
ã«ã«æº¶è§£ãïŒâã«ãŠããªãšãã«ã¢ãã³3.2ïœãã
ã€ãã滎äžããé€ã ã«å®€æž©ãšããã宀枩ã§äžæ©æŸ
眮ããã®ã¡ã溶åªãçå»ããã¡ã¿ããŒã«50mlãå
ãããïŒâã«å·åŽåŸããã«10ïŒ æ°Žé žåãããªãŠã
氎溶液50ïœã滎äžããïŒæéåå¿ãããåå¿åŸåž
å¡©é žã§äžåããé ¢é žãšãã«ã§æœåºããææ©å±€ãã·
ãªã«ã²ã«ãã©ãã·ãŠã«ã©ã ã¯ãããã°ã©ãã€ãŒã«
ãŠæ éã«åé¢ãããäž»çæç©ãšããŠç®çç©3.0ïœ
ãæœç¶ç©ãšããŠåŸããåç23.4ïŒ NMRããŒã¿ïŒCDCl3ïŒÎŽ.36ïŒ1HãïœïŒã7.98ïŒ1Hã
ddïŒã7.75ïŒ1HãïœïŒã5.57ïŒ1HãïœïŒã3.43
ïŒ2HãïœïŒã1.32ïŒ9HãïœïŒ å®æœäŸ ïŒ åææ³ããã«ããååç©ïŒâïœâããã«â
ïŒâïŒïŒââã¡ãã«ââãããµãã·ã«ã¹ã«
ãã¢ã¢ã€ã«âïŒâãããããšãã«ïŒâïŒâã€ãœ
ãªããµãŸãªã³âïŒâãªã³ã®åæ åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâããããã·ã€ãœãªããµãŸ
ãŒã«ã®åæ ããããã·ã«ã¢ãã³å¡©é žå¡©583.7ïœã4Nâæ°Žé ž
åãããªãŠã 氎溶液ïŒã«æº¶è§£ããæ°·å·äžãšã¿ã
ãŒã«ïŒãæ·»å ããæŽã«4Nâæ°Žé žåãããªãŠã
æ°Žâãšã¿ããŒã«ïŒïŒïŒïŒïŒæ··å溶液ãå ããŠæº¶æ¶²
ã®PHã10.0ã«èª¿æŽããããã®æº¶æ¶²ã«ãããã€ã«é ¢
é žãšãã«ãšã¹ãã«1380ïœãš4Nâæ°Žé žåãããªãŠ
ã æ°Žâãšã¿ããŒã«ïŒïŒïŒïŒïŒæ··å溶液ãåå¿æº¶æ¶²
ã®PHã10±0.2ã枩床ãïŒãïŒâã«ãªãæ§ã«åæ
ã«æ»Žäžããã 滎äžçµäºåŸã宀枩ã§ïŒæéæ¹æåŸãïŒâã®æ¿å¡©
é žæ°ŽïŒKgã«æ³šã12æéæŸçœ®ãããæåºããçµæ¶ã
åããååã«æ°ŽæŽåŸã也ç¥ãããåé770ïœã
åç68.2ïŒ ãèç¹99âã101â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâããããã³ãŒã³ã¹ã«ããã«ã¯
ãã©ã€ãã®åæ ïŒâã¯ããâïŒâããããã³ãŒã³ã¹ã«ãã³é žã«
ãªãŠã 1280ïœãšã¢ã»ããããªã«1150mlãã¹ã«ãã©
ã³250mlãšãžã¡ãã«ã¢ã»ãã¢ãã30mlã®æ··å溶液
ã«ããªãã·å¡©åãªã³1250mlãå æž©60âã70âã«ä¿
ã€æ§ã«æ»Žäžããã73âã§ïŒæéåå¿åŸãæ°Žå·ãã
æ°Ž400mlãåŸã ã«æ·»å ããåŸãæ°·æ°ŽïŒã«æ³šãã ã
æåºããçµæ¶ãåããæ°ŽæŽåŸä¹Ÿç¥ããã åé1060ïœãåç84ïŒ ãèç¹55âã56â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâãããââãããµãã·ã«ã
ã³ãŒã³ã¹ã«ãã³ã¢ããã®åæ ïŒâã¯ããâïŒâãããâãã³ãŒã³ã¹ã«ããã«
ã¯ãã©ã€ã800ïœã«ãžã¯ããã¡ã¿ã³ïŒãå ãïŒ
âã«å·åŽããããã®æº¶æ¶²ã«ãããµãã·ã«ã¢ãã³
600ïœãããªãšãã«ã¢ãã³251mlããžã¯ããã¡ã¿ã³
780mlã®æ··åç©ã20ã30âã«ãŠæ»Žäžããã宀枩ã§
ïŒæéåå¿åŸããžã¯ãã«ã¡ã¿ã³ãæžå§äžçå»ãã
æ®æž£ã«ã¡ã¿ããŒã«ïŒãå ãå ç±æº¶è§£ãããåŸå·
ããŠå®€æž©ã§æ¶æåŸæŽã«ã¡ã¿ããŒã«ïŒãå ã氷什
äžæ¶æããçµæ¶ãåã也ç¥ããã åé1020ïœãåç88ïŒ ãèç¹91âã93â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâãããââã¡ãã«ââã
ããµãã·ã«ãã³ãŒã³ã¹ã«ãã³ã¢ããã®åæ ïŒâã¯ããâïŒâãããââãããµãã·ã«ã
ã³ãŒã³ã¹ã«ãã³ã¢ãã170ïœãã¢ã»ãã³640mlã«æº¶
解ããçé žã«ãªãŠã 79ïœãããªãšãã¬ã³ã°ãªã³ãŒ
ã«400 ïŒmlããžã¡ãã«ç¡«é ž71ïœãå ãïŒæéå ç±
éæµãããããã«ã¢ã»ãã³240mlãå ã40âã§æ°Ž
870mlã滎äžã宀枩ãŸã§å·åŽãããšçµæ¶ãæåºã
ããçµæ¶ãåããæ°Žãã¡ã¿ããŒã«ã§æŽã也ç¥ã
ãã åé169ïœãåç97ïŒ ãèç¹74âã75â åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒââã¡ãã«ââ
ãããµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããš
ãã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ åæäŸïŒâïŒã§åæããïŒâã¯ããâïŒâãã
ãââãããµãã·ã«ãã³ãŒã³ã¹ã«ãã³ã¢ãã
470ïœãåæäŸïŒã§åæããïŒâïœâããã«âïŒ
âããããã·ã€ãœãªããµãŸãŒã«169ïœãçé žã«ãª
ãŠã 168ïœããžã¡ãã«ã¹ã«ããã·ã1.2ãæ··åã
65âã§ïŒæéåå¿ããã åå¿æ¶²ãæ°·æ°Žã«æ³šãæåºããçµæ¶ãåããæ°Ž
æŽåŸä¹Ÿç¥ããã åé576ïœãåç100ïŒ ãèç¹67âã68â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
15.0ïœãïŒâïœâããã«âïŒâããããã·ã€ãœãª
ããµãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ã
ã«ã¹ã«ããã·ã80mlãæ··åãã80âã§ïŒæéåå¿
ãããå·åŽåŸæ°Žã«æ³šãæåºããçµæ¶ããåãæ°Žâ
ã¡ã¿ããŒã«ããåçµæ¶ãããåé10.0ïœãåç
45.5ïŒ ãèç¹116ã117â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãšããã·ã«ã«ãã
ã«âïŒâãããããšãã«ïŒã€ãœãªããµãŸãªã³â
ïŒâãªã³ã®åæ 23.0ïœã®ïŒâã¯ããâïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ãš17ïœã®ïŒâïœâããã«âïŒâããã
ãã·ã€ãœãªããµãŸãŒã«ã100mlã®ãžã¡ãã«ã¹ã«ã
ãã·ãã«æº¶è§£ãããã«17ïœã®çé žã«ãªãŠã ãå
ãã75âã«ãŠïŒæéåå¿ãããåå¿çµäºåŸãåå¿
æ··åç©ãå·åŽå¡©é žã«æ³šãæ¹æãããšãã ã¡ã«ç¡è²
çµæ¶ãæåºããããã®çµæ¶ããåãããšã¿ããŒã«
ããåçµæ¶ãããåé3.7ïœãåç94.8ïŒ ãèç¹
88â å®æœäŸ ïŒ ååç©ã®åæ åæäŸ ïŒâïŒ ïŒ®âã¡ãã«ââãªã¯ã¿ãã·ã«âïŒâãããâ
ïŒâã¯ããâãã³ãã¢ããã®åæ 105.7ïœã®ïŒâãããâïŒâã¯ããå®æ¯éŠé žãš
800mlã®ã¢ã»ããããªã«ãæ··åããããã«å¡©åã
ãªãã«68.6ïœãå ããïŒæéå ç±éæµãããå·åŽ
åŸã溶åªãçå»ãã¯ãããã«ã ã«æº¶è§£ããããã®
溶液ã«ããªãšãã«ã¢ãã³63.5ïœãå ããïŒâãšã
ããã€ãã«ïŒ®âã¡ãã«ãªã¯ã¿ãã·ã«ã¢ãã³148.6
ïœã®ã¯ãããã«ã 溶液ãããã«æ»Žäžãããåå¿çµ
äºåŸãæ°Žãå ãå液ããåŸãææ©çžãç¡æ°Žç¡«é žã
ããªãŠã ã§ä¹Ÿç¥ãããç¡æ©ç©ããå¥ããã®ã¡æº¶åª
ãçå»ããã¢ã»ããããªã«âã¡ã¿ããŒã«ïŒïŒïŒ
ïŒïŒããåçµæ¶ãããåé186ïœãåç76.0ïŒ ã
èç¹55ã56â åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒââã¡ãã«ââ
ãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ 34.1ïœã®ïŒ®âã¡ãã«âãªã¯ã¿ãã·ã«âïŒâãã
ãâïŒâã¯ãããã³ãã¢ããã12.4ïœã®ïŒâïœâ
ããã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã12.4
ïœã®çé žã«ãªãŠã ã«ãžã¡ãã«ãã«ã ã¢ãã300ml
ãå ãã100âã«ãŠïŒæéåå¿ããã溶åªãæžå§
çå»ãé ¢é žãšãã«ãšæ°Žãå ããŠæ¹æããã®ã¡ææ©
çžããšããã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒ
ã§äž»çæç©ãååãããïœâãããµã³âé ¢é žãšã
ã«ããåçµæ¶ãããåé18.0ïœãåç43.1ïŒ ãè
ç¹64âã å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãšããã·ã«ã«ãã
ã«âïŒâãããµãã·ã«ãªãã·âïŒâãããããš
ãã«ïŒã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 65ïœã®ïŒâã¯ããâïŒâãããµãã·ã«ãªãã·â
ïŒâãããå®æ¯éŠé žãšãã«ãšã¹ãã«ã24ïœã®ïŒâ
ïœâããã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã
300mlã®ãžã¡ãã«ã¹ã«ããã·ãã«æº¶è§£ããããã«
24ïœã®çé žã«ãªãŠã ãå ãã75âã§ïŒæéåå¿ã
ããåå¿çµäºåŸåå¿æ··åç©ãåžå¡©é žã«æ³šããé ¢é ž
ãšãã«ãå ããæœåºãããææ©çžã也ç¥åŸã溶åª
ãçå»ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§
泚ææ·±ãååãããäž»çæç©ãšããŠãæšèšååç©
ãåŸããããåŸãããååç©ãã¡ã¿ããŒã«âã¢ã»
ããããªã«ããåçµæ¶ãããåé30.1ïœãåç
37.9ïŒ ãèç¹35ã36â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããããšãã«ïŒ
ã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 5.0ïœã®ïŒâãã«ãªãããããã³ãŒã³ãš5.0ïœã®
ïŒâïœâããã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã«ã4.0ïœã®ã«ãªãŠã ïœâãããã·ããš70mlã®ã
ã«ãšã³ãæ··åãã0.5ïœã®ïŒâïŒïŒâãšãã«ããã·
ã«ïŒããªãžããŠã ã¯ããªããå ã10æéå ç±éæµ
ãããåå¿æ··åç©ãå·åŽåŸãã·ãªã«ã«ã©ã ã¯ãã
ãã°ã©ãã€ãŒã§æ³šææ·±ãååããŠãæšèšååç©ã
åŸããåé0.6ïœãåç6.5ïŒ ãèç¹125ã127â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒïŒïŒâãžãããããš
ãã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®å
æ ïŒïŒïŒâãžããããã«ãªããã³ãŒã³3.7ïœã20
mlã®ãžã¡ãã«ãã«ã ã¢ããã2.9ïœã®ïŒâïœâã
ãã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã2.8ïœ
ã®çé žã«ãªãŠã ãæ··åãã80â30ååå¿ããå·åŽ
åŸãæ°Žâé ¢é žãšãã«ãå ãæœåºããã溶åªãæžå§
çå»åŸããšãŒãã«âé ¢é žãšãã«ããçµæ¶åããã
åé1.9ïœãåç30.9ïŒ ãèç¹167ã168â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâãããâïŒâã¯ãã«ãã³ãŸããªãã«ãªãªã
15.0ïœãïŒâïœâããã«âïŒâããããã·ã€ãœãª
ããµãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ã
ã«ã¹ã«ããã·ã80mlãæ··åãã100âã§ïŒæéå
å¿ãããåå¿åŸãæ°·æ°Žã«æ³šãé ¢é žãšãã«ã§æœåºã
ãåŸãææ©å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ã
ã€ãŒã§åé¢ããäž»çæç©ãšãããã¡ã¿ããŒã«âæ°Ž
ããåçµæ¶ãè¡ãªãç®çç©4.1ïœãåŸããåç
18.7ïŒ ãèç¹125ã126â å®æœäŸ 10 ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
15ïœãïŒâïœâããã«ïŒâããããã·ã€ãœãªããµ
ãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ãã«ã¹
ã«ããã·ã80mlãæ··åãã80âã§ïŒæéåå¿ã
ãã å·åŽåŸãé ¢é žãšãã«ãšæ°Žãå ãæœåºãããææ©
å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§åé¢
ããã¡ã¿ããŒã«âæ°Žããåçµæ¶ãè¡ãªãç®çç©ã
åŸãã åé8.8ïœãåç40.1ïŒ ãèç¹59ã60â å®æœäŸ 11 ååç©ã®åæ ïŒâã¡ãã«âïŒâïŒïŒâãžã¡ãã«ã¹ã«ãã¢ã¢ã€
ã«âïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ãžãšãã«ïŒâã¯ãã«âïŒâããããã³ãŒã³ã¹ã«
ãã³ã¢ãã27.9ïœãïŒâã¡ãã«âïŒâããããã·
ã€ãœãªããµãŸãŒã«11.9ïœãçé žæ°ŽçŽ ãããªãŠã
16.8ïœã120mlã®ãžã¡ãã«ã¹ã«ããã·ããšæ··åãã
70âã§ïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ãã¡ã¿ããŒã«âæ°Žããåçµæ¶ããã åé29.5ãåç86.3ïŒ ãèç¹141ã142â å®æœäŸ 12 ååç©äŸåæ ïŒâã¡ãã«âïŒâïŒïŒââã¡ãã«ââãã
ãµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ âã¡ãã«ââãããµãã·ã«ïŒâã¯ããâïŒ
âããããã³ãŒã³ã¹ã«ãã³ã¢ãã16ïœãïŒâãã
ããã·âïŒâã¡ãã«ã€ãœãªããµãŸãŒã«4.8ïœãç
é žæ°ŽçŽ ãããªãŠã 6.4ïœããžã¡ãã«ã¹ã«ããã·ã
48mlãæ··åãã75âã§ïŒæéåå¿ãããåå¿åŸå·
åŽãã75mlã®ã¡ã¿ããŒã«ãå ããã®ã¡æ°Ž35mlãã
ã€ãã滎äžããæåºããçµæ¶ããåããã¡ã¿ããŒ
ã«âã¢ã»ããããªã«ïŒïŒïŒïŒïŒããåçµæ¶ããã åé17.2ïœãåç95.1ïŒ ãèç¹63ã65â å®æœäŸ 13 ååç©äŸããã®åæ ïŒâã¡ãã«âïŒâïŒïŒâãšããã·ã«ã«ããã«â
ïŒâãããããšãã«ïŒã€ãœãªããµãŸãªã³âïŒâ
ãªã³ã®åæ 400ïœã®ïŒâã¯ããâïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ã1.2ã®ãžã¡ãã«ã¹ã«ããã·ãã270
ïœã®ïŒâã¡ãã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã«ã292ïœã®çé žã«ãªãŠã ãæ··åãã10æé60â
ã§åå¿ãããå·åŽåŸæ··åç©ãæ°Žã«æ³šããæåºãã
çµæ¶ãé ¢é žãšãã«ããåçµæ¶ãããåé300.1ïœã
åç59.0ïŒ ãèç¹122ã123â å®æœäŸ 14 ååç©äŸããã®åæ ïŒâïœâããã«âïŒâïŒïŒïŒïŒâãã¹âã¡ã¿ã³
ã¹ã«ããã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãªã³
âïŒâãªã³ã®åæ ïŒïœã®ïŒïŒïŒâãã¹âã¡ã¿ã³ã¹ã«ããã«ã¯ãã«
ãã³ãŒã³ãšïŒïœã®ïŒâïœâããã«âïŒâãããã
ã·ã€ãœãªããµãŸãŒã«ãïŒïœã®çé žã«ãªãŠã ããžã¡
ãã«ã¹ã«ããã·ããšæ··åãã80âã§ïŒæéåå¿ã
ããåå¿åŸäºåŸåå¿æ¶²ãæ°Žã«ããé ¢é žãšãã«ãå
ãæœåºãããé ¢é žãšãã«ãæžå§çå»ããæ®æž£ãæ°Ž
âã¡ã¿ããŒã«ããåçµæ¶ããã åé0.85ïœãåç61.2ïŒ ãèç¹166ã168â å®æœäŸ 15 ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒââ
ã¡ãã«ââãªã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«ããš
ãã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®å
æ âã¡ãã«ââãªã¯ã¿ãã·ã«ïŒâã¯ããâïŒ
âããããã³ãŒã³ã¹ã«ãã³ã¢ãã62ïœããžã¡ãã«
ãã«ã ã¢ãã220mlãïŒâïœâããã«âïŒâãã
ããã·ã€ãœãªããµãŸãŒã«20.9ïœãçé žã«ãªãŠã
20.7ïœãæ··åãã80âãïŒæéåå¿ãããåå¿æ¶²
ãå¡©é žã§é žæ§ãšããã®ã¡ããžã¡ãã«ãã«ã ã¢ãã
ãçå»ããæ°Žãé ¢é žãšãã«ãå ãæœåºããã ææ©å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒ
ã§ç²Ÿè£œãäž»çæç©ãååãç®çç©ãåŸãã åé29ïœãåç38.8ïŒ ãèç¹55ã56â å®æœäŸ 16 ååç©äŸããã®åæ åæäŸ 16âïŒ ïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâããããã·
ã€ãœãªããµãŸãŒã«ã®åæ Canadian Journal of Chemistry62å·»ã1940
é ïŒ1984ïŒã®æ¹æ³ã®å€æ³ã«ãŠåæãããïŒåå¿æº¶
åªãæ°Žãããæ°ŽïŒãšã¿ããŒã«ïŒïŒïŒïŒãšããŠåå¿
ããåå¿çµäºåŸãç容éã®æ¿å¡©é žãšæ··åãïŒæé
å ç±éæµåŸå·åŽæåºããçµæ¶ããéããã åç41.8ïŒ ãèç¹191ã193âïŒåè§£ïŒ åæäŸ 16âïŒ ïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâïŒïŒâãã
ãâïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒâïŒâ
ã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
20.0ïœãïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâãã
ããã·ã€ãœãªããµãŸãŒã«20.0ïœãçé žã«ãªãŠã
16.0ïœããžã¡ãã«ã¹ã«ããã·ã120mlãæ··åãã
60âãïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ããžã¡ãã«ãã«ã ã¢ããâã¡ã¿ããŒã«ããå
çµæ¶ããã åé30.5ïœãèç¹170ã171â å®æœäŸ 17 ååç©äŸãã®åæ åæäŸ 17âïŒ ïŒâããšãã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã« Chemcal and Pharmaceutical Bulletin14å·»
11å·1277ã1286é ïŒ1966ïŒã«èšèŒã®æ¹æ³ã«åŸã€ãŠ
åæããã åæäŸ 17âïŒ ïŒâããšãã«âïŒâïŒïŒââã¡ãã«ââãª
ã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ ïŒâãããâïŒââã¡ãã«ââãªã¿ãã·ã«
ã¹ã«ãã¢ã¢ã€ã«âïŒâã¯ãããã³ãŒã³50.3ïœãšå
æäŸ17âïŒã§åæããïŒâããšãã«âïŒâããã
ãã·ã€ãœãªããµãŸãŒã«19.3ïœããžã¡ãã«ãã«ã ã¢
ããã«æº¶è§£ã16.8ïœã®çé žã«ãªãŠã ãããã80â
ã§ïŒæéåå¿ãããã€ãã«ç¡æ©ç©ããå¥ããã®ã¡
溶åªãæžå§çå»ããã¡ã¿ããŒã«ããçµæ¶åãã
ããåé52.2ïœãåç83.2ïŒ ãèç¹93ã94â å®æœäŸ 18 ååç©äŸããã®åæ ïŒâããšãã«âïŒâïŒïŒââã¡ãã«ââã
ããµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 300ïœã®ïŒ®âã¡ãã«ââãããµãã·ã«âïŒâ
ã¯ãã«âïŒâããããã³ãŒã³ã¹ã«ãã³ã¢ããã
122ïœã®ïŒâããšãã«âïŒâããããã·ã€ãœãªã
ãµãŸãŒã«ã800ïœã®ãžã¡ãã«ã¹ã«ããã·ãã106ïœ
ã®çé žã«ãªãŠã ãæ··åãã60âã§ïŒæéåå¿ã
ããåå¿çµäºåŸå·åŽãåå¿æ··åç©ãæ°Žã«æ³šãã ã
çµæ¶ããéããåŸãæ°ŽæŽãã¡ã¿ããŒã«ã§æŽæµãã
ã®ã¡ã也ç¥ãããåé376ïœãåç99.3ïŒ ãèç¹
88ã89â å®æœäŸ 19 ååç©äŸããã®åæ ïŒâïŒïŒâã¢ã»ãã«ã¢ããããšãã«ïŒâïŒâïŒïŒ
âãããâïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒ
âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
6.4ïœãïŒâïŒïŒâã¢ã»ãã«ã¢ããããšãã«âïŒâ
ããããã·ã€ãœãªããµãŸãŒã«7.0ïœãçé žã«ãªãŠ
ã 4.5ïœããžã¡ãã«ã¹ã«ããã·ã50mlãæ··åãã
70âã§ïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ããžã¡ãã«ãã«ã ã¢ããâã¡ã¿ããŒã«ããå
çµæ¶ããã åé8.8ïœãåç75.9ïŒ ãèç¹238ã239â å®æœäŸ 20 ååç©äŸããã®åæ ïŒâããšãã«âïŒïŒâãšããã·ã«ã«ããã«âïŒ
âãããããšãã«ïŒã€ãœãªããµãŸãªã³âïŒâãª
ã³ã®åæ 200ïœã®ïŒâã¯ãã«âïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ã500mlã®ãžã¡ãã«ã¹ã«ããã·ãã169
ïœã®ïŒâããšãã«ã€ãœãªããµãŸãŒã«ã146ïœã®ç
é žã«ãªãŠã ãæ··åãã60âã§ïŒæéåå¿ãããå·
åŽåŸæ°Žã«æ³šãã§æåºããçµæ¶ãæ°ŽæŽã也ç¥ããã åé292ïœãåç94.6ïŒ ãèç¹142ã143â å®æœäŸ 21 ååç©äŸãã®åæ ïŒâããšãã«âïŒâïŒïŒâãããâïŒâããªã
ã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãª
ã³âïŒâãªã³ã®åæ ïŒâã¯ãã«âïŒâããããã³ãŸããªãã«ãªãªã
22.6ïœãïŒâããšãã«âïŒâããããã·ã€ãœãªã
ãµãŸãŒã«19.3ïœãçé žã«ãªãŠã 16.8ïœããžã¡ãã«
ã¹ã«ããã·ã150mlãæ··åãã70âãïŒæéåå¿
ãããå·åŽåŸãæ°Žã«æ³šãæåºããçµæ¶ããžã¡ãã«
ãã«ã ã¢ããâã¡ã¿ããŒã«ããåçµæ¶ããã åé28.4ïœãåç95.0ïŒ ãèç¹185ã187â å®æœäŸ 22 ååç©ããã®åæ ïŒâïœâããã«âïŒâïŒïŒâã¡ã¿ã³ã¹ã«ããã«
âïŒâããã©ãã·ã«ã¹ã«ããã«ããšãã«ïŒâïŒ
âã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 32ïœã®ïŒâã¡ã¿ã³ã¹ã«ããã«âïŒâããã©ãã·
ã«ã¹ã«ããã«ã¯ãã«ãã³ãŒã³ã20ïœã®ïŒâïœâã
ãã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã20ïœã®
çé žã«ãªãŠã ã140mlã®ãžã¡ãã«ã¹ã«ããã·ãã
æ··åãã80âã§ïŒæéåå¿ãããåå¿çµäºåŸåå¿
æ··åç©ãæ°Žã«ãããé ¢é žãšãã«ã§æœåºããææ©å±€
ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œ
ããç®çç©ãäž»çæç©ãšããŠåŸããåé20.0ïœã
åç50.8ïŒ ãèç¹97ã98â åèäŸ ä»¥äžã«ãæ¬çºæã®ååç©ãçšããŠããã²ã³åé
åçæå ææçšã®ãã·äœçšååç©ãåæããäŸã
瀺ãã åèåæäŸ ïŒâïŒ ïŒâã¯ããã¡ãã«âïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«
âïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸã
ã³ã®åæ å®æœäŸïŒã§åæããïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³36
ïœããã©ãã«ã ã¢ã«ããã5.7ïœãå¡©åäºé10.3
ïœãé ¢é ž250mlãšæ··åããå¡©åæ°ŽçŽ ã¬ã¹ãå¹ã蟌
ã¿ãªãã100â20æéåå¿ãããåå¿çµäºåŸãå·
åŽãåå¿æ··åç©ãæ°·æ°Žã«ããããæåºããåºäœã
ãåããã¯ãããã«ã ã«æº¶è§£ãã«ã©ã ã¯ãããã°
ã©ãã€ãŒã§ç²Ÿè£œãããåé10.0ïœãåç25.6ïŒ ã
èç¹77âã åèåæäŸ ïŒâïŒ ïŒâïŒïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããã·ïŒã¡ãã«âïŒâïœâããã«âïŒâïŒïŒâ
âã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³
ã®åæ ïŒâã¯ããã¡ãã«âïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³
10.0ïœãšïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããŒã«4.0ïœãçé žã«ãªãŠã 3.0ïœãã¢ã»ãã³100
mlãšæ··åããïŒæéå ç±éæµããã åå¿çµäºåŸãã¢ã»ãã³ãçå»ããé ¢é žãšãã«â
æ°Žãå ãæœåºãè¡ãªã€ããææ©çžãã·ãªã«ã²ã«ã«
ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œãããåé9.0ïœã
åç70.5ïŒ åèåæäŸ ïŒâïŒ ïŒâïŒïŒâã¢ããããšããã·ïŒã¡ãã«âïŒâïœ
âããã«âïŒâïŒïŒââã¡ãã«ââãªã¯ã¿
ãã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšãã«ïŒâ
ïŒâã€ãœãªããµãŸãã³ã®åæ ïŒâïŒïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããã·ïŒã¡ãã«âïŒâïœâããã«âïŒâïŒïŒâ
âã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«âïŒâ
ãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³9.0ïœã
ã¯ãããã«ã ã«æº¶è§£ããïŒâ以äžã«å·åŽãããã€
ãã§ãããã«ããªãã«ãªãé ¢é ž10mlããã€ãã滎
äžãããé€ã ã«å®€æž©ãšããŠ10æéåå¿ãããåå¿
çµäºåŸãåå¿æ··åç©ãéæ¹æ°Žã«ããäžåããé ¢é ž
ãšãã«ã§æœåºãããæœåºç©ãã·ãªã«ã²ã«ãã©ãã·
ãŠã«ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œãããåé
6.9ïœãåç90.8ïŒ ã åèåæäŸ ïŒâïŒ ããžäœçšååç©äŸïŒ¡ã®åæ ïŒâïŒïŒâã¢ããããšããã·ïŒã¡ãã«âïŒâïœ
âããã«âïŒâïŒïŒââã¡ãã«ââãªã¯ã¿ã
ã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšãã«ïŒâïŒâ
ã€ãœãªããµãŸãã³5.4ïœã40mlã®ã¯ãããã«ã ã«
溶解ãïŒâã«å·åŽãããããã«ããªãžã³0.8ïœã
å ããã®ã¡ãäžèšååç©A3.1ïœãæ·»å ãïŒæé
åå¿ããã ååç©ïŒ¡
åéã«ãããŠãããžäœçšååç©ãšåŒã°ãããé žå
éå åå¿ãè¡ãªãåççã«æçšãªè©Šè¬ãæŸåºãã
ååç©çŸ€ã®äžã§ããšãããéèŠãªäžçŸ€ã®ååç©ã
åæããããã®éèŠäžéäœã§ããã æ¬çºæã®ååç©ãäžéäœãšããããžäœçšååç©
ã¯äŸãã°ãç¹é¡æ60â244873å·ãç¹é¡æ61â
88625å·ãç¹é¡æ61â88623å·ãç¹é¡æ61â89502
å·ãç¹é¡æ61â130342å·ãç¹é¡æ61â136947å·ã«
èšèŒãããŠãããšãããå€ãã®æçšæ§ãæããŠã
ãããŸããïŒâã¢ãªãŒã«âïŒâã€ãœãªããµãŸãªã³
âïŒâãªã³èªå°äœã¯é€èå€ã殺èå€ãé®çå€ãæ¶
çå€ãªã©ãšããŠã®è¬çäœçšãæããŠããçç掻æ§
ç©è³ªãšããŠãéèŠãªæå³ãæããŠããã 以äžã«å®æœäŸãæ²ããæ¬çºæãæŽã«è©³çŽ°ã«èª¬æ
ããã å®æœäŸ ïŒ åææ³ããã«ããååç©äŸããïŒâïœâããã«
âïŒâïŒïŒâããã·ã«ã¹ã«ããã«âïŒâããªãã«
ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãªã³â
ïŒâãªã³ã®åæã åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâãã©ãŸãªãã³ã®åæ 1.0Kgã®ãããã€ã«é ¢é žãšãã«ã2.5ã®ãšã¿ã
ãŒã«ã«æº¶è§£ããæ°Žå·äž320ïœã®å æ°Žããã©ãžã³ã
滎äžããã滎äžçµäºåŸã宀枩ã«ãŠäžæ©åå¿ããã®
ã¡5.0ã®æ°Žãæ·»å ãæ¹æãããæåºããçµæ¶ã
æžå§ãéããæ°Žã§è¯ãæŽæµããã®ã¡å°éã®ã¡ã¿ã
ãŒã«ã§æŽã颚也ãããåé812ïœãåç98.5ïŒ ã åæäŸ ïŒâïŒïŒïŒïŒâãžããã âïŒâïœâãã
ã«âïŒâãã©ãŸãªãã³ã®åæ ïŒâïœâããã«âïŒâãã©ãŸãªãã³658ïœã2.0
ã®é ¢é žã«æº¶è§£ãããæ°Žå·äžãæ¹æããªãããã®
溶液ã«èçŽ 1.5Kgã滎äžããã滎äžçµäºåŸãäžæ©
åå¿ããã®ã¡5.0ã®æ°Žãæ·»å ãããæåºããçµ
æ¶ãæžå§ãéããæ°Žã§è¯ãæŽæµããã®ã¡å°éã®ã¡
ã¿ããŒã«ã§æŽã颚也ãããåé1.36Kgãåç97.2
ïŒ ã åæäŸ ïŒâïŒ ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«é žã®åæ 552ïœã®æ°Žé žåãããªãŠã ã3.0ã®æ°Žã«æº¶è§£
ããæ°·ãå ããŠïŒâ以äžãšãããã€ãã§æ¹æããª
ããããžããã âïŒâïœâããã«âïŒâãã©ãŸãª
ãã³ãïŒâ以äžã«ä¿ã¡ãªããå°éãã€æ·»å ããã
枩床ãäžæããå Žåã«ã¯æ°·ã®çºæ³¡ãé²ãããã«ã¢
ã»ããããªã«ãæ·»å ãããåå¿çµäºåŸã6Nå¡©é ž
ã§é žæ§ãšããã®ã¡é ¢é žãšãã«ãå ãïŒåºŠæœåºã
ãã æœåºæ¶²ã¯ç¡æ°Žç¡«é žãããªãŠã ã§ä¹Ÿç¥ããåŸãé ¢
é žãšãã«ãæžå§çå»ãããæ®æž£ã®ãªã€ã«ãïŒïŒïŒ
âãžã¡ãã«âïŒâãã³ããªãŒã«é žã§ãã€ãããã®
ãªã€ã«ã¯ç²Ÿè£œãã次ã®åå¿ã«çšããã åæäŸ ïŒâïŒ ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«é žã¯ããª
ãã®åæ 466ïœã®ïŒïŒïŒâãžã¡ãã«âïŒâãã³ããªãŒã«
é žã3.5ã®å¡©åã¡ãã¬ã³ã«æ··åããæ¹æããã
ããã«483ïœã®å¡©åããªãã«ãå ãïŒæéåå¿åŸã
å ç±éæµãããšæ¿ããå¡©åæ°ŽçŽ ã¬ã¹ãçºçããã
ïŒæéå ç±éæµããã®ã¡ã溶åªãçå»ãæžå§èžç
ãè¡ãªã€ããç®çç©ã¯ç¡è²ã®æ¶²äœã§ãbp.20çŽ70
âã§ãã€ããåé290ïœãåç54.3ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ããªâïŒâããããã³ãŸããªãã«ãª
ãªãã®åæ 56.4ïœã®ïŒâã¯ããâïŒâããããã³ãŸããªã
ã«ãªãªãã44ïœã®ãã·ã«ã¡ã«ã«ãã¿ã³ã50ïœã®ã
ããªãŠã ã¡ããã·ãã300mlã®ã¡ã¿ããŒã«ãæ··å
ãã80âïŒæéåå¿ãããå·åŽåŸæ°·æ°Žã«æ³šãæåº
ããçµæ¶ããåãããåé88.0ïœãåçã96.9
ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã³ãŸããª
ãã«ãªãªãã®åæ 86ïœã®ïŒâãã·ã«ããªâïŒâããããã³ãŸããª
ãã«ãªãªãã300mlã®é ¢é žãæ··åããïŒïœã®ã¿ã³
ã°ã¹ãã³é žãããªãŠã ãå ãã70âã«å ç±ããã
ããã«35ïŒ éé žåæ°ŽçŽ æ°Ž46mlã80ã85âã«ä¿ã¡ãª
ãã滎äžããã滎äžçµäºåŸããã®æž©åºŠã§ïŒæéå
å¿ãããåå¿åŸãæ°Žã«æ³šãæåºããçµæ¶ããåã
也ç¥ãããåé93.1ïœãåç99.3ïŒ ã åæäŸ ïŒâïŒ ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã·ã¢ãã
ãã³ãŸããªãã«ãªãªãã®åæ 100ïœã®ïŒâãã·ã«ã¹ã«ããã«âïŒâãããã
ã³ãŸããªãã«ãªãªãã100ïœã®äºéç²æ«ã450mlã®
ãšã¿ããŒã«ãæ··åãã50ã65âã«ä¿ã¡ãªãã10ïŒ
å¡©åã¢ã³ã¢ããŠã 氎溶液ã滎äžãããåå¿çµäº
åŸãã»ã©ã€ãããããŠããéãè¡ãªãäžæº¶ç©ãé€
å»ããã®ã¡ãæ°Žã«æ³šããé ¢é žãšãã«ã§æœåºããã
溶åªãçå»åŸïœâãããµã³ããåçµæ¶ãããåé
80.2ïœãåç84ïŒ åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒâãã·ã«ã¹ã«ããã«
âïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€
ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 10ïœã®ïŒâãã·ã«ã¹ã«ããã«âïŒâããããã·
ã¢ãããã³ãŸããªãã«ãªãªããš4.2ïœã®ïŒïŒïŒâ
ãžã¡ãã«ãã³ããªãŒã«é žã¯ããªãã80mlã®ãšãŒã
ã«ã«æº¶è§£ãïŒâã«ãŠããªãšãã«ã¢ãã³3.2ïœãã
ã€ãã滎äžããé€ã ã«å®€æž©ãšããã宀枩ã§äžæ©æŸ
眮ããã®ã¡ã溶åªãçå»ããã¡ã¿ããŒã«50mlãå
ãããïŒâã«å·åŽåŸããã«10ïŒ æ°Žé žåãããªãŠã
氎溶液50ïœã滎äžããïŒæéåå¿ãããåå¿åŸåž
å¡©é žã§äžåããé ¢é žãšãã«ã§æœåºããææ©å±€ãã·
ãªã«ã²ã«ãã©ãã·ãŠã«ã©ã ã¯ãããã°ã©ãã€ãŒã«
ãŠæ éã«åé¢ãããäž»çæç©ãšããŠç®çç©3.0ïœ
ãæœç¶ç©ãšããŠåŸããåç23.4ïŒ NMRããŒã¿ïŒCDCl3ïŒÎŽ.36ïŒ1HãïœïŒã7.98ïŒ1Hã
ddïŒã7.75ïŒ1HãïœïŒã5.57ïŒ1HãïœïŒã3.43
ïŒ2HãïœïŒã1.32ïŒ9HãïœïŒ å®æœäŸ ïŒ åææ³ããã«ããååç©ïŒâïœâããã«â
ïŒâïŒïŒââã¡ãã«ââãããµãã·ã«ã¹ã«
ãã¢ã¢ã€ã«âïŒâãããããšãã«ïŒâïŒâã€ãœ
ãªããµãŸãªã³âïŒâãªã³ã®åæ åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâããããã·ã€ãœãªããµãŸ
ãŒã«ã®åæ ããããã·ã«ã¢ãã³å¡©é žå¡©583.7ïœã4Nâæ°Žé ž
åãããªãŠã 氎溶液ïŒã«æº¶è§£ããæ°·å·äžãšã¿ã
ãŒã«ïŒãæ·»å ããæŽã«4Nâæ°Žé žåãããªãŠã
æ°Žâãšã¿ããŒã«ïŒïŒïŒïŒïŒæ··å溶液ãå ããŠæº¶æ¶²
ã®PHã10.0ã«èª¿æŽããããã®æº¶æ¶²ã«ãããã€ã«é ¢
é žãšãã«ãšã¹ãã«1380ïœãš4Nâæ°Žé žåãããªãŠ
ã æ°Žâãšã¿ããŒã«ïŒïŒïŒïŒïŒæ··å溶液ãåå¿æº¶æ¶²
ã®PHã10±0.2ã枩床ãïŒãïŒâã«ãªãæ§ã«åæ
ã«æ»Žäžããã 滎äžçµäºåŸã宀枩ã§ïŒæéæ¹æåŸãïŒâã®æ¿å¡©
é žæ°ŽïŒKgã«æ³šã12æéæŸçœ®ãããæåºããçµæ¶ã
åããååã«æ°ŽæŽåŸã也ç¥ãããåé770ïœã
åç68.2ïŒ ãèç¹99âã101â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâããããã³ãŒã³ã¹ã«ããã«ã¯
ãã©ã€ãã®åæ ïŒâã¯ããâïŒâããããã³ãŒã³ã¹ã«ãã³é žã«
ãªãŠã 1280ïœãšã¢ã»ããããªã«1150mlãã¹ã«ãã©
ã³250mlãšãžã¡ãã«ã¢ã»ãã¢ãã30mlã®æ··å溶液
ã«ããªãã·å¡©åãªã³1250mlãå æž©60âã70âã«ä¿
ã€æ§ã«æ»Žäžããã73âã§ïŒæéåå¿åŸãæ°Žå·ãã
æ°Ž400mlãåŸã ã«æ·»å ããåŸãæ°·æ°ŽïŒã«æ³šãã ã
æåºããçµæ¶ãåããæ°ŽæŽåŸä¹Ÿç¥ããã åé1060ïœãåç84ïŒ ãèç¹55âã56â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâãããââãããµãã·ã«ã
ã³ãŒã³ã¹ã«ãã³ã¢ããã®åæ ïŒâã¯ããâïŒâãããâãã³ãŒã³ã¹ã«ããã«
ã¯ãã©ã€ã800ïœã«ãžã¯ããã¡ã¿ã³ïŒãå ãïŒ
âã«å·åŽããããã®æº¶æ¶²ã«ãããµãã·ã«ã¢ãã³
600ïœãããªãšãã«ã¢ãã³251mlããžã¯ããã¡ã¿ã³
780mlã®æ··åç©ã20ã30âã«ãŠæ»Žäžããã宀枩ã§
ïŒæéåå¿åŸããžã¯ãã«ã¡ã¿ã³ãæžå§äžçå»ãã
æ®æž£ã«ã¡ã¿ããŒã«ïŒãå ãå ç±æº¶è§£ãããåŸå·
ããŠå®€æž©ã§æ¶æåŸæŽã«ã¡ã¿ããŒã«ïŒãå ã氷什
äžæ¶æããçµæ¶ãåã也ç¥ããã åé1020ïœãåç88ïŒ ãèç¹91âã93â åæäŸ ïŒâïŒ ïŒâã¯ããâïŒâãããââã¡ãã«ââã
ããµãã·ã«ãã³ãŒã³ã¹ã«ãã³ã¢ããã®åæ ïŒâã¯ããâïŒâãããââãããµãã·ã«ã
ã³ãŒã³ã¹ã«ãã³ã¢ãã170ïœãã¢ã»ãã³640mlã«æº¶
解ããçé žã«ãªãŠã 79ïœãããªãšãã¬ã³ã°ãªã³ãŒ
ã«400 ïŒmlããžã¡ãã«ç¡«é ž71ïœãå ãïŒæéå ç±
éæµãããããã«ã¢ã»ãã³240mlãå ã40âã§æ°Ž
870mlã滎äžã宀枩ãŸã§å·åŽãããšçµæ¶ãæåºã
ããçµæ¶ãåããæ°Žãã¡ã¿ããŒã«ã§æŽã也ç¥ã
ãã åé169ïœãåç97ïŒ ãèç¹74âã75â åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒââã¡ãã«ââ
ãããµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããš
ãã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ åæäŸïŒâïŒã§åæããïŒâã¯ããâïŒâãã
ãââãããµãã·ã«ãã³ãŒã³ã¹ã«ãã³ã¢ãã
470ïœãåæäŸïŒã§åæããïŒâïœâããã«âïŒ
âããããã·ã€ãœãªããµãŸãŒã«169ïœãçé žã«ãª
ãŠã 168ïœããžã¡ãã«ã¹ã«ããã·ã1.2ãæ··åã
65âã§ïŒæéåå¿ããã åå¿æ¶²ãæ°·æ°Žã«æ³šãæåºããçµæ¶ãåããæ°Ž
æŽåŸä¹Ÿç¥ããã åé576ïœãåç100ïŒ ãèç¹67âã68â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
15.0ïœãïŒâïœâããã«âïŒâããããã·ã€ãœãª
ããµãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ã
ã«ã¹ã«ããã·ã80mlãæ··åãã80âã§ïŒæéåå¿
ãããå·åŽåŸæ°Žã«æ³šãæåºããçµæ¶ããåãæ°Žâ
ã¡ã¿ããŒã«ããåçµæ¶ãããåé10.0ïœãåç
45.5ïŒ ãèç¹116ã117â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãšããã·ã«ã«ãã
ã«âïŒâãããããšãã«ïŒã€ãœãªããµãŸãªã³â
ïŒâãªã³ã®åæ 23.0ïœã®ïŒâã¯ããâïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ãš17ïœã®ïŒâïœâããã«âïŒâããã
ãã·ã€ãœãªããµãŸãŒã«ã100mlã®ãžã¡ãã«ã¹ã«ã
ãã·ãã«æº¶è§£ãããã«17ïœã®çé žã«ãªãŠã ãå
ãã75âã«ãŠïŒæéåå¿ãããåå¿çµäºåŸãåå¿
æ··åç©ãå·åŽå¡©é žã«æ³šãæ¹æãããšãã ã¡ã«ç¡è²
çµæ¶ãæåºããããã®çµæ¶ããåãããšã¿ããŒã«
ããåçµæ¶ãããåé3.7ïœãåç94.8ïŒ ãèç¹
88â å®æœäŸ ïŒ ååç©ã®åæ åæäŸ ïŒâïŒ ïŒ®âã¡ãã«ââãªã¯ã¿ãã·ã«âïŒâãããâ
ïŒâã¯ããâãã³ãã¢ããã®åæ 105.7ïœã®ïŒâãããâïŒâã¯ããå®æ¯éŠé žãš
800mlã®ã¢ã»ããããªã«ãæ··åããããã«å¡©åã
ãªãã«68.6ïœãå ããïŒæéå ç±éæµãããå·åŽ
åŸã溶åªãçå»ãã¯ãããã«ã ã«æº¶è§£ããããã®
溶液ã«ããªãšãã«ã¢ãã³63.5ïœãå ããïŒâãšã
ããã€ãã«ïŒ®âã¡ãã«ãªã¯ã¿ãã·ã«ã¢ãã³148.6
ïœã®ã¯ãããã«ã 溶液ãããã«æ»Žäžãããåå¿çµ
äºåŸãæ°Žãå ãå液ããåŸãææ©çžãç¡æ°Žç¡«é žã
ããªãŠã ã§ä¹Ÿç¥ãããç¡æ©ç©ããå¥ããã®ã¡æº¶åª
ãçå»ããã¢ã»ããããªã«âã¡ã¿ããŒã«ïŒïŒïŒ
ïŒïŒããåçµæ¶ãããåé186ïœãåç76.0ïŒ ã
èç¹55ã56â åæäŸ ïŒâïŒ ïŒâïœâããã«âïŒâïŒïŒââã¡ãã«ââ
ãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ 34.1ïœã®ïŒ®âã¡ãã«âãªã¯ã¿ãã·ã«âïŒâãã
ãâïŒâã¯ãããã³ãã¢ããã12.4ïœã®ïŒâïœâ
ããã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã12.4
ïœã®çé žã«ãªãŠã ã«ãžã¡ãã«ãã«ã ã¢ãã300ml
ãå ãã100âã«ãŠïŒæéåå¿ããã溶åªãæžå§
çå»ãé ¢é žãšãã«ãšæ°Žãå ããŠæ¹æããã®ã¡ææ©
çžããšããã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒ
ã§äž»çæç©ãååãããïœâãããµã³âé ¢é žãšã
ã«ããåçµæ¶ãããåé18.0ïœãåç43.1ïŒ ãè
ç¹64âã å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãšããã·ã«ã«ãã
ã«âïŒâãããµãã·ã«ãªãã·âïŒâãããããš
ãã«ïŒã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 65ïœã®ïŒâã¯ããâïŒâãããµãã·ã«ãªãã·â
ïŒâãããå®æ¯éŠé žãšãã«ãšã¹ãã«ã24ïœã®ïŒâ
ïœâããã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã
300mlã®ãžã¡ãã«ã¹ã«ããã·ãã«æº¶è§£ããããã«
24ïœã®çé žã«ãªãŠã ãå ãã75âã§ïŒæéåå¿ã
ããåå¿çµäºåŸåå¿æ··åç©ãåžå¡©é žã«æ³šããé ¢é ž
ãšãã«ãå ããæœåºãããææ©çžã也ç¥åŸã溶åª
ãçå»ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§
泚ææ·±ãååãããäž»çæç©ãšããŠãæšèšååç©
ãåŸããããåŸãããååç©ãã¡ã¿ããŒã«âã¢ã»
ããããªã«ããåçµæ¶ãããåé30.1ïœãåç
37.9ïŒ ãèç¹35ã36â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããããšãã«ïŒ
ã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 5.0ïœã®ïŒâãã«ãªãããããã³ãŒã³ãš5.0ïœã®
ïŒâïœâããã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã«ã4.0ïœã®ã«ãªãŠã ïœâãããã·ããš70mlã®ã
ã«ãšã³ãæ··åãã0.5ïœã®ïŒâïŒïŒâãšãã«ããã·
ã«ïŒããªãžããŠã ã¯ããªããå ã10æéå ç±éæµ
ãããåå¿æ··åç©ãå·åŽåŸãã·ãªã«ã«ã©ã ã¯ãã
ãã°ã©ãã€ãŒã§æ³šææ·±ãååããŠãæšèšååç©ã
åŸããåé0.6ïœãåç6.5ïŒ ãèç¹125ã127â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒïŒïŒâãžãããããš
ãã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®å
æ ïŒïŒïŒâãžããããã«ãªããã³ãŒã³3.7ïœã20
mlã®ãžã¡ãã«ãã«ã ã¢ããã2.9ïœã®ïŒâïœâã
ãã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã2.8ïœ
ã®çé žã«ãªãŠã ãæ··åãã80â30ååå¿ããå·åŽ
åŸãæ°Žâé ¢é žãšãã«ãå ãæœåºããã溶åªãæžå§
çå»åŸããšãŒãã«âé ¢é žãšãã«ããçµæ¶åããã
åé1.9ïœãåç30.9ïŒ ãèç¹167ã168â å®æœäŸ ïŒ ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâãããâïŒâã¯ãã«ãã³ãŸããªãã«ãªãªã
15.0ïœãïŒâïœâããã«âïŒâããããã·ã€ãœãª
ããµãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ã
ã«ã¹ã«ããã·ã80mlãæ··åãã100âã§ïŒæéå
å¿ãããåå¿åŸãæ°·æ°Žã«æ³šãé ¢é žãšãã«ã§æœåºã
ãåŸãææ©å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ã
ã€ãŒã§åé¢ããäž»çæç©ãšãããã¡ã¿ããŒã«âæ°Ž
ããåçµæ¶ãè¡ãªãç®çç©4.1ïœãåŸããåç
18.7ïŒ ãèç¹125ã126â å®æœäŸ 10 ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒâããª
ãã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
15ïœãïŒâïœâããã«ïŒâããããã·ã€ãœãªããµ
ãŸãŒã«11.3ïœãçé žã«ãªãŠã 11.0ïœããžã¡ãã«ã¹
ã«ããã·ã80mlãæ··åãã80âã§ïŒæéåå¿ã
ãã å·åŽåŸãé ¢é žãšãã«ãšæ°Žãå ãæœåºãããææ©
å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§åé¢
ããã¡ã¿ããŒã«âæ°Žããåçµæ¶ãè¡ãªãç®çç©ã
åŸãã åé8.8ïœãåç40.1ïŒ ãèç¹59ã60â å®æœäŸ 11 ååç©ã®åæ ïŒâã¡ãã«âïŒâïŒïŒâãžã¡ãã«ã¹ã«ãã¢ã¢ã€
ã«âïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸ
ãªã³âïŒâãªã³ã®åæ ãžãšãã«ïŒâã¯ãã«âïŒâããããã³ãŒã³ã¹ã«
ãã³ã¢ãã27.9ïœãïŒâã¡ãã«âïŒâããããã·
ã€ãœãªããµãŸãŒã«11.9ïœãçé žæ°ŽçŽ ãããªãŠã
16.8ïœã120mlã®ãžã¡ãã«ã¹ã«ããã·ããšæ··åãã
70âã§ïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ãã¡ã¿ããŒã«âæ°Žããåçµæ¶ããã åé29.5ãåç86.3ïŒ ãèç¹141ã142â å®æœäŸ 12 ååç©äŸåæ ïŒâã¡ãã«âïŒâïŒïŒââã¡ãã«ââãã
ãµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ âã¡ãã«ââãããµãã·ã«ïŒâã¯ããâïŒ
âããããã³ãŒã³ã¹ã«ãã³ã¢ãã16ïœãïŒâãã
ããã·âïŒâã¡ãã«ã€ãœãªããµãŸãŒã«4.8ïœãç
é žæ°ŽçŽ ãããªãŠã 6.4ïœããžã¡ãã«ã¹ã«ããã·ã
48mlãæ··åãã75âã§ïŒæéåå¿ãããåå¿åŸå·
åŽãã75mlã®ã¡ã¿ããŒã«ãå ããã®ã¡æ°Ž35mlãã
ã€ãã滎äžããæåºããçµæ¶ããåããã¡ã¿ããŒ
ã«âã¢ã»ããããªã«ïŒïŒïŒïŒïŒããåçµæ¶ããã åé17.2ïœãåç95.1ïŒ ãèç¹63ã65â å®æœäŸ 13 ååç©äŸããã®åæ ïŒâã¡ãã«âïŒâïŒïŒâãšããã·ã«ã«ããã«â
ïŒâãããããšãã«ïŒã€ãœãªããµãŸãªã³âïŒâ
ãªã³ã®åæ 400ïœã®ïŒâã¯ããâïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ã1.2ã®ãžã¡ãã«ã¹ã«ããã·ãã270
ïœã®ïŒâã¡ãã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã«ã292ïœã®çé žã«ãªãŠã ãæ··åãã10æé60â
ã§åå¿ãããå·åŽåŸæ··åç©ãæ°Žã«æ³šããæåºãã
çµæ¶ãé ¢é žãšãã«ããåçµæ¶ãããåé300.1ïœã
åç59.0ïŒ ãèç¹122ã123â å®æœäŸ 14 ååç©äŸããã®åæ ïŒâïœâããã«âïŒâïŒïŒïŒïŒâãã¹âã¡ã¿ã³
ã¹ã«ããã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãªã³
âïŒâãªã³ã®åæ ïŒïœã®ïŒïŒïŒâãã¹âã¡ã¿ã³ã¹ã«ããã«ã¯ãã«
ãã³ãŒã³ãšïŒïœã®ïŒâïœâããã«âïŒâãããã
ã·ã€ãœãªããµãŸãŒã«ãïŒïœã®çé žã«ãªãŠã ããžã¡
ãã«ã¹ã«ããã·ããšæ··åãã80âã§ïŒæéåå¿ã
ããåå¿åŸäºåŸåå¿æ¶²ãæ°Žã«ããé ¢é žãšãã«ãå
ãæœåºãããé ¢é žãšãã«ãæžå§çå»ããæ®æž£ãæ°Ž
âã¡ã¿ããŒã«ããåçµæ¶ããã åé0.85ïœãåç61.2ïŒ ãèç¹166ã168â å®æœäŸ 15 ååç©ã®åæ ïŒâïœâããã«âïŒâïŒïŒâãããâïŒââ
ã¡ãã«ââãªã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«ããš
ãã«ïŒâïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®å
æ âã¡ãã«ââãªã¯ã¿ãã·ã«ïŒâã¯ããâïŒ
âããããã³ãŒã³ã¹ã«ãã³ã¢ãã62ïœããžã¡ãã«
ãã«ã ã¢ãã220mlãïŒâïœâããã«âïŒâãã
ããã·ã€ãœãªããµãŸãŒã«20.9ïœãçé žã«ãªãŠã
20.7ïœãæ··åãã80âãïŒæéåå¿ãããåå¿æ¶²
ãå¡©é žã§é žæ§ãšããã®ã¡ããžã¡ãã«ãã«ã ã¢ãã
ãçå»ããæ°Žãé ¢é žãšãã«ãå ãæœåºããã ææ©å±€ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒ
ã§ç²Ÿè£œãäž»çæç©ãååãç®çç©ãåŸãã åé29ïœãåç38.8ïŒ ãèç¹55ã56â å®æœäŸ 16 ååç©äŸããã®åæ åæäŸ 16âïŒ ïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâããããã·
ã€ãœãªããµãŸãŒã«ã®åæ Canadian Journal of Chemistry62å·»ã1940
é ïŒ1984ïŒã®æ¹æ³ã®å€æ³ã«ãŠåæãããïŒåå¿æº¶
åªãæ°Žãããæ°ŽïŒãšã¿ããŒã«ïŒïŒïŒïŒãšããŠåå¿
ããåå¿çµäºåŸãç容éã®æ¿å¡©é žãšæ··åãïŒæé
å ç±éæµåŸå·åŽæåºããçµæ¶ããéããã åç41.8ïŒ ãèç¹191ã193âïŒåè§£ïŒ åæäŸ 16âïŒ ïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâïŒïŒâãã
ãâïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒâïŒâ
ã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
20.0ïœãïŒâïŒïŒâã¡ããã·ããšãã«ïŒâïŒâãã
ããã·ã€ãœãªããµãŸãŒã«20.0ïœãçé žã«ãªãŠã
16.0ïœããžã¡ãã«ã¹ã«ããã·ã120mlãæ··åãã
60âãïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ããžã¡ãã«ãã«ã ã¢ããâã¡ã¿ããŒã«ããå
çµæ¶ããã åé30.5ïœãèç¹170ã171â å®æœäŸ 17 ååç©äŸãã®åæ åæäŸ 17âïŒ ïŒâããšãã«âïŒâããããã·ã€ãœãªããµãŸãŒ
ã« Chemcal and Pharmaceutical Bulletin14å·»
11å·1277ã1286é ïŒ1966ïŒã«èšèŒã®æ¹æ³ã«åŸã€ãŠ
åæããã åæäŸ 17âïŒ ïŒâããšãã«âïŒâïŒïŒââã¡ãã«ââãª
ã¯ã¿ãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒâïŒâã€ãœãªããµãŸãã³ã®åæ ïŒâãããâïŒââã¡ãã«ââãªã¿ãã·ã«
ã¹ã«ãã¢ã¢ã€ã«âïŒâã¯ãããã³ãŒã³50.3ïœãšå
æäŸ17âïŒã§åæããïŒâããšãã«âïŒâããã
ãã·ã€ãœãªããµãŸãŒã«19.3ïœããžã¡ãã«ãã«ã ã¢
ããã«æº¶è§£ã16.8ïœã®çé žã«ãªãŠã ãããã80â
ã§ïŒæéåå¿ãããã€ãã«ç¡æ©ç©ããå¥ããã®ã¡
溶åªãæžå§çå»ããã¡ã¿ããŒã«ããçµæ¶åãã
ããåé52.2ïœãåç83.2ïŒ ãèç¹93ã94â å®æœäŸ 18 ååç©äŸããã®åæ ïŒâããšãã«âïŒâïŒïŒââã¡ãã«ââã
ããµãã·ã«ã¹ã«ãã¢ã¢ã€ã«âïŒâãããããšã
ã«ïŒã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 300ïœã®ïŒ®âã¡ãã«ââãããµãã·ã«âïŒâ
ã¯ãã«âïŒâããããã³ãŒã³ã¹ã«ãã³ã¢ããã
122ïœã®ïŒâããšãã«âïŒâããããã·ã€ãœãªã
ãµãŸãŒã«ã800ïœã®ãžã¡ãã«ã¹ã«ããã·ãã106ïœ
ã®çé žã«ãªãŠã ãæ··åãã60âã§ïŒæéåå¿ã
ããåå¿çµäºåŸå·åŽãåå¿æ··åç©ãæ°Žã«æ³šãã ã
çµæ¶ããéããåŸãæ°ŽæŽãã¡ã¿ããŒã«ã§æŽæµãã
ã®ã¡ã也ç¥ãããåé376ïœãåç99.3ïŒ ãèç¹
88ã89â å®æœäŸ 19 ååç©äŸããã®åæ ïŒâïŒïŒâã¢ã»ãã«ã¢ããããšãã«ïŒâïŒâïŒïŒ
âãããâïŒâããªãã«ãªãã¡ãã«ããšãã«ïŒ
âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ ïŒâã¯ããâïŒâããããã³ãŸããªãã«ãªãªã
6.4ïœãïŒâïŒïŒâã¢ã»ãã«ã¢ããããšãã«âïŒâ
ããããã·ã€ãœãªããµãŸãŒã«7.0ïœãçé žã«ãªãŠ
ã 4.5ïœããžã¡ãã«ã¹ã«ããã·ã50mlãæ··åãã
70âã§ïŒæéåå¿ãããåå¿åŸæ°Žã«æ³šãæåºãã
çµæ¶ããžã¡ãã«ãã«ã ã¢ããâã¡ã¿ããŒã«ããå
çµæ¶ããã åé8.8ïœãåç75.9ïŒ ãèç¹238ã239â å®æœäŸ 20 ååç©äŸããã®åæ ïŒâããšãã«âïŒïŒâãšããã·ã«ã«ããã«âïŒ
âãããããšãã«ïŒã€ãœãªããµãŸãªã³âïŒâãª
ã³ã®åæ 200ïœã®ïŒâã¯ãã«âïŒâãããå®æ¯éŠé žãšã
ã«ãšã¹ãã«ã500mlã®ãžã¡ãã«ã¹ã«ããã·ãã169
ïœã®ïŒâããšãã«ã€ãœãªããµãŸãŒã«ã146ïœã®ç
é žã«ãªãŠã ãæ··åãã60âã§ïŒæéåå¿ãããå·
åŽåŸæ°Žã«æ³šãã§æåºããçµæ¶ãæ°ŽæŽã也ç¥ããã åé292ïœãåç94.6ïŒ ãèç¹142ã143â å®æœäŸ 21 ååç©äŸãã®åæ ïŒâããšãã«âïŒâïŒïŒâãããâïŒâããªã
ã«ãªãã¡ãã«ããšãã«ïŒâïŒâã€ãœãªããµãŸãª
ã³âïŒâãªã³ã®åæ ïŒâã¯ãã«âïŒâããããã³ãŸããªãã«ãªãªã
22.6ïœãïŒâããšãã«âïŒâããããã·ã€ãœãªã
ãµãŸãŒã«19.3ïœãçé žã«ãªãŠã 16.8ïœããžã¡ãã«
ã¹ã«ããã·ã150mlãæ··åãã70âãïŒæéåå¿
ãããå·åŽåŸãæ°Žã«æ³šãæåºããçµæ¶ããžã¡ãã«
ãã«ã ã¢ããâã¡ã¿ããŒã«ããåçµæ¶ããã åé28.4ïœãåç95.0ïŒ ãèç¹185ã187â å®æœäŸ 22 ååç©ããã®åæ ïŒâïœâããã«âïŒâïŒïŒâã¡ã¿ã³ã¹ã«ããã«
âïŒâããã©ãã·ã«ã¹ã«ããã«ããšãã«ïŒâïŒ
âã€ãœãªããµãŸãªã³âïŒâãªã³ã®åæ 32ïœã®ïŒâã¡ã¿ã³ã¹ã«ããã«âïŒâããã©ãã·
ã«ã¹ã«ããã«ã¯ãã«ãã³ãŒã³ã20ïœã®ïŒâïœâã
ãã«âïŒâããããã·ã€ãœãªããµãŸãŒã«ã20ïœã®
çé žã«ãªãŠã ã140mlã®ãžã¡ãã«ã¹ã«ããã·ãã
æ··åãã80âã§ïŒæéåå¿ãããåå¿çµäºåŸåå¿
æ··åç©ãæ°Žã«ãããé ¢é žãšãã«ã§æœåºããææ©å±€
ãã·ãªã«ã²ã«ã«ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œ
ããç®çç©ãäž»çæç©ãšããŠåŸããåé20.0ïœã
åç50.8ïŒ ãèç¹97ã98â åèäŸ ä»¥äžã«ãæ¬çºæã®ååç©ãçšããŠããã²ã³åé
åçæå ææçšã®ãã·äœçšååç©ãåæããäŸã
瀺ãã åèåæäŸ ïŒâïŒ ïŒâã¯ããã¡ãã«âïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«
âïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸã
ã³ã®åæ å®æœäŸïŒã§åæããïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³36
ïœããã©ãã«ã ã¢ã«ããã5.7ïœãå¡©åäºé10.3
ïœãé ¢é ž250mlãšæ··åããå¡©åæ°ŽçŽ ã¬ã¹ãå¹ã蟌
ã¿ãªãã100â20æéåå¿ãããåå¿çµäºåŸãå·
åŽãåå¿æ··åç©ãæ°·æ°Žã«ããããæåºããåºäœã
ãåããã¯ãããã«ã ã«æº¶è§£ãã«ã©ã ã¯ãããã°
ã©ãã€ãŒã§ç²Ÿè£œãããåé10.0ïœãåç25.6ïŒ ã
èç¹77âã åèåæäŸ ïŒâïŒ ïŒâïŒïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããã·ïŒã¡ãã«âïŒâïœâããã«âïŒâïŒïŒâ
âã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³
ã®åæ ïŒâã¯ããã¡ãã«âïŒâïœâããã«âïŒâïŒïŒ
ââã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«â
ïŒâãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³
10.0ïœãšïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããŒã«4.0ïœãçé žã«ãªãŠã 3.0ïœãã¢ã»ãã³100
mlãšæ··åããïŒæéå ç±éæµããã åå¿çµäºåŸãã¢ã»ãã³ãçå»ããé ¢é žãšãã«â
æ°Žãå ãæœåºãè¡ãªã€ããææ©çžãã·ãªã«ã²ã«ã«
ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œãããåé9.0ïœã
åç70.5ïŒ åèåæäŸ ïŒâïŒ ïŒâïŒïŒâã¢ããããšããã·ïŒã¡ãã«âïŒâïœ
âããã«âïŒâïŒïŒââã¡ãã«ââãªã¯ã¿
ãã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšãã«ïŒâ
ïŒâã€ãœãªããµãŸãã³ã®åæ ïŒâïŒïŒâïœâãããã·ã«ã«ããã«ã¢ããããš
ããã·ïŒã¡ãã«âïŒâïœâããã«âïŒâïŒïŒâ
âã¡ãã«ââãªã¯ã¿ãã·ã«ã«ã«ãã¢ã€ã«âïŒâ
ãããããšãã«ïŒâïŒâã€ãœãªããµãŸãã³9.0ïœã
ã¯ãããã«ã ã«æº¶è§£ããïŒâ以äžã«å·åŽãããã€
ãã§ãããã«ããªãã«ãªãé ¢é ž10mlããã€ãã滎
äžãããé€ã ã«å®€æž©ãšããŠ10æéåå¿ãããåå¿
çµäºåŸãåå¿æ··åç©ãéæ¹æ°Žã«ããäžåããé ¢é ž
ãšãã«ã§æœåºãããæœåºç©ãã·ãªã«ã²ã«ãã©ãã·
ãŠã«ã©ã ã¯ãããã°ã©ãã€ãŒã§ç²Ÿè£œãããåé
6.9ïœãåç90.8ïŒ ã åèåæäŸ ïŒâïŒ ããžäœçšååç©äŸïŒ¡ã®åæ ïŒâïŒïŒâã¢ããããšããã·ïŒã¡ãã«âïŒâïœ
âããã«âïŒâïŒïŒââã¡ãã«ââãªã¯ã¿ã
ã·ã«ã«ã«ãã¢ã€ã«âïŒâãããããšãã«ïŒâïŒâ
ã€ãœãªããµãŸãã³5.4ïœã40mlã®ã¯ãããã«ã ã«
溶解ãïŒâã«å·åŽãããããã«ããªãžã³0.8ïœã
å ããã®ã¡ãäžèšååç©A3.1ïœãæ·»å ãïŒæé
åå¿ããã ååç©ïŒ¡
ãåŒã
åå¿çµäºåŸãã¯ãããã«ã ãçå»ããå°éã®
DMFã«æº¶è§£ãã¡ã¿ããŒã«ãæ²¹ç¶ç©ãæåºããªã
çšåºŠãŸã§å ãããæ¹æãããšçµæ¶ãæåºãããã
ã®çµæ¶ããåããå床åæ§ã®ç²Ÿè£œãè¡ãªãäžèšã®
ããžäœçšååç©ïŒ¡ãåŸããåé3.9ïœãåç46.5
ïŒ ãèç¹157ã159âã ããžäœçšååç©ïŒ¡
DMFã«æº¶è§£ãã¡ã¿ããŒã«ãæ²¹ç¶ç©ãæåºããªã
çšåºŠãŸã§å ãããæ¹æãããšçµæ¶ãæåºãããã
ã®çµæ¶ããåããå床åæ§ã®ç²Ÿè£œãè¡ãªãäžèšã®
ããžäœçšååç©ïŒ¡ãåŸããåé3.9ïœãåç46.5
ïŒ ãèç¹157ã159âã ããžäœçšååç©ïŒ¡
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒããã§è¡šããããååç© ãåŒã åŒäžR1ã¯ã¢ã«ãã«åºãã¢ãªãŒã«åºã§ããã R2ãR3ãR4ã¯æ°ŽçŽ ååãã¢ã«ã³ãã·åºãã¢ã·
ã«åºãã¢ã«ã³ãã·ã«ã«ããã«åºãã¢ãªãŒã«ãªãã·
ã«ã«ããã«åºãããã²ã³ååããããåºãã«ã«ã
ã¢ã€ã«åºãã¹ã«ãã¢ã¢ã€ã«åºãã¹ã«ããã«åºãã·
ã¢ãåºãããªãã«ãªãã¡ãã«åºã®äžããéžã°ãã
åºã§ãR2ãR3ã®ãã¡å°ãªããšãäžã€ã¯ã·ã¢ãåºã
ã¹ã«ããã«åºãã¹ã«ãã€ãã«åºãããªãã«ãªãã¡
ãã«åºããããåºãã®äžããéžã°ããïŒâã¢ãªãŒ
ã«âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠãR1ãççŽ
æ°ïŒãïŒã®ã¢ã«ãã«åºã§ããåŒããã§è¡šããã
ãååç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠãR1ãççŽ
æ°ïŒã12ã®ã¢ãªãŒã«åºã§ããåŒããã§è¡šããã
ãååç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠR2ãããã¯
R3ã®ãã¡å°ãªããšãäžæ¹ããããåºã§ããåŒ
ããã§è¡šããããååç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠR2ããã³R3
ãããªãã«ãªãã¡ãã«åºãã·ã¢ãåºãã¹ã«ããã«
åºã®äžããéžã°ããåŒããã§è¡šããããåå
ç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠãR2ããã
ã¯R3ã®ãã¡å°ãªããšãäžæ¹ããããåºã§ããåŒ
ããã§è¡šããããååç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠR2ãããã¯
R3ã®ãã¡å°ãªããšãäžæ¹ããããåºã§ããåŒ
ããã§è¡šããããååç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠR2ãR3ãR4
ã®ãã¡å°ãªããšãäžã€ãã¹ã«ããã«åºãã¹ã«ãã¢
ã¢ã€ã«åºãã¢ã«ã³ãã·ã«ã«ããã«åºãã«ã«ãã¢ã€
ã«åºãã¢ã·ã«åºãããªãã«ãªãã¡ãã«åºãã·ã¢ã
åºã®äžããéžã°ããåŒããã§è¡šããããåå
ç©ã ïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠãR2ãR3ã
R4ã®ãã¡å°ãªããšãäžã€ããã¹ã«ããã«åºãã¹
ã«ãã¢ã¢ã€ã«åºãã¢ã«ã³ãã·ã«ã«ããã«åºãã«ã«
ãã¢ã€ã«åºãã¢ã·ã«åºãããªãã«ãªãã¡ãã«åºã
ã·ã¢ãåºã®äžããéžã°ããåŒããã§è¡šãããã
ååç©ã ïŒïŒ ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«ãããŠR2ããã
ãåºã§ããR3ãã¹ã«ãã¢ã¢ã€ã«åºãã«ã«ãã¢ã€
ã«åºãã¢ã«ã³ãã·ã«ã«ããã«åºãããªãã«ãªãã¡
ãã«åºã®äžããéžã°ããåºã§R4ãæ°ŽçŽ ååã§ã
ãåŒããã§è¡šããããååç©ã
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2544287A JPS63192761A (ja) | 1987-02-05 | 1987-02-05 | ïŒâã¢ãªâã«âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœ |
US07/819,661 US5221750A (en) | 1987-02-05 | 1992-01-13 | 2-aryl-4-isoxazolin-3-one derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2544287A JPS63192761A (ja) | 1987-02-05 | 1987-02-05 | ïŒâã¢ãªâã«âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœ |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63192761A JPS63192761A (ja) | 1988-08-10 |
JPH0575748B2 true JPH0575748B2 (ja) | 1993-10-21 |
Family
ID=12166116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2544287A Granted JPS63192761A (ja) | 1987-02-05 | 1987-02-05 | ïŒâã¢ãªâã«âïŒâã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœ |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63192761A (ja) |
-
1987
- 1987-02-05 JP JP2544287A patent/JPS63192761A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS63192761A (ja) | 1988-08-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HU200322B (en) | Process for producing new alkane sulfonanilide derivatives | |
US4165428A (en) | Indoleacetic acid ester derivatives | |
JPH0575748B2 (ja) | ||
US4950764A (en) | 2-aryl-4-isoxazolin-3-one derivatives | |
JP4144978B2 (ja) | ïŒïŒïŒïŒïŒâãã¢ãžã¢ãŸãŒã«èªå°äœã®åææ³ | |
JPH0567148B2 (ja) | ||
JP2527587B2 (ja) | âã¹ã«ããã«âïœâïŒã¯ãããã©ãŸãªã«ïŒã¢ãããªãã·ã ã®è£œé æ¹æ³ | |
JP4075357B2 (ja) | ïŒïŒïŒâãžçœ®æâïŒïŒïŒïŒïŒâããªã¢ãŸãŒã«åã³ãã®è£œé æ³ | |
US5221750A (en) | 2-aryl-4-isoxazolin-3-one derivatives | |
JP2531461B2 (ja) | ã¢ãããã§ãã«ããªé ¢é žé¡ | |
JPH0751561B2 (ja) | 眮æãã§ãã«ããªé ¢é ž | |
JPH08109172A (ja) | ïŒïŒšâïŒïŒïŒïŒïŒâããªã¢ãŸãŒã«èªå°äœåã³ïŒïŒšâãããâãïŒïŒïŒâïœããïŒïŒïŒïŒïŒãããªã¢ãŸãŒã«èªå°äœ | |
JPH0625135B2 (ja) | ããŒã³ã¿ã«ãã©âã®è£œé æ¹æ³ | |
EP0679634B1 (en) | Method for producing a 3-oxo-propionic acid amide compound and substituted acetyl compound used therein | |
US4374253A (en) | Method for preparing 1-aryl-3-arylamino-2-pyrazolin-5-ones from N-aryl-3-arylamino-3-oximinopropionamides | |
JP3776962B2 (ja) | ïŒâ眮æâïŒâãªããœâïŒâããããããªã³é žã¢ããååç©åã³ïŒâ眮æâïŒâãªããœâïŒâïŒïŒïŒïŒâãžã¡ãã«ããã³ãã€ã³âïŒâã€ã«ïŒããããªã³é žã¢ããååç©ã®è£œé æ¹æ³ | |
JPH0714923B2 (ja) | ã€ãœãªããµãŸãªã³âïŒâãªã³èªå°äœã®åææ³ | |
JP2531460B2 (ja) | ã¢ããªã³èªå°äœ | |
JPS63250368A (ja) | ïŒâã¢ã«ã³ãã·âïŒâã¢ããâïŒïœâãã©ãŸâã«é¡ã®è£œé æ¹æ³ | |
JPH0456027B2 (ja) | ||
JP2524793B2 (ja) | ïŒâããªçœ®æãã§ãâã«ååç©ã®è£œé æ¹æ³ | |
JP3951432B2 (ja) | è€çŽ ç°ã¢ãŸã¡ãã³è²çŽ ã®è£œé æ¹æ³ | |
JP3896399B2 (ja) | ïŒâãªããœããããªã³é žã¢ããååç©ã®è£œé æ¹æ³ | |
AU750356B2 (en) | 1,5-diphenylpyrazole derivatives | |
JPH0260665B2 (ja) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |