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【结 构 式】

【分子编号】57909

【品名】Fumaryl chloride

【CA登记号】627-63-4

【 分 子 式 】C4H2Cl2O2

【 分 子 量 】152.96408

【元素组成】C 31.41% H 1.32% Cl 46.35% O 20.92%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The Friedel Crafts condensation of fumaryl chloride (I) with bromobenzene (II) gives 1,2-bis(4-bromobenzoyl)ethylene (III), which is reduced with Zn and Ac-OH to yield 1,4-bis(4-bromophenyl)butane-1,4-dione (IV). The cyclization of (IV) in refluxing Ac2O affords 2,5-bis(4-bromophenyl)furan (V), which is treated with CNCu in refluxing quinoline to provide 2,5-bis(4-cyanophenyl)furan (VI). The reaction of (VI) with HCl in ethanol gives the bis imidate (VII), which is finally treated with O-methylhydroxylamine to yield the target bis O-methylamidooxime.

3 Tidwell, R.R.; Hall, J.E.; Kumar, A.; Dykstra, C.C.; Boykin, D.W.; Wilson, W.D.; Blagburn, B.L. (Auburn University; Georgia State University; University of North Carolina); Furan derivs. for inhibiting Pneumocystis carinii pneumonia, Giardia lamblia and Cryptosporidium parvum. WO 9615126 .
1 Boykin, D.W.; et al.; Anti-pneumocystis activity of bis-amidoximes and bis-O-alkylamidoximes prodrugs. Bioorg Med Chem Lett 1996, 6, 24, 3017.
2 Boykin, D.W.; et al.; 2,5-Bis[4-(N-alkylamidino)phenyl]furans as anti-Pneumocystis carinii agents. J Med Chem 1998, 41, 1, 124.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 57909 Fumaryl chloride 627-63-4 C4H2Cl2O2 详情 详情
(II) 13365 Monobromobenzene; 1-Bromobenzene;Phenylbromide;bromobenzene 108-86-1 C6H5Br 详情 详情
(III) 57910 (E)-1,4-bis(4-bromophenyl)-2-butene-1,4-dione C16H10Br2O2 详情 详情
(IV) 35811 1,4-bis(4-bromophenyl)-1,4-butanedione C16H12Br2O2 详情 详情
(V) 35812 2,5-bis(4-bromophenyl)furan C16H10Br2O 详情 详情
(VI) 35814 4-[5-(4-cyanophenyl)-2-furyl]benzonitrile C18H10N2O 详情 详情
(VII) 35815 ethyl 4-(5-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate C22H22N2O3 详情 详情
(VIII) 15455 (aminooxy)methane; O-methylhydroxylamine 67-62-9 CH5NO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The Friedel Crafts condensation of fumaryl chloride (I) with bromobenzene (II) gives 1,2-bis(4-bromobenzoyl)ethylene (III), which is reduced with Zn and Ac-OH to yield 1,4-bis(4-bromophenyl)butane-1,4-dione (IV). The cyclization of (IV) in refluxing Ac2O affords 2,5-bis(4-bromophenyl)furan (V) which is treated with CNCu in refluxing quinoline to provide 2,5-bis(4-cyanophenyl)furan (VI). The reaction of (VI) with HCl in ethanol gives the bis imidate (VII), which is finally treated with ammonia in ethanol to yield the target bis benzamidine.

1 Dann, O.; et al.; Trypanocidal diamidines with three isolated ring systems. Liebigs Ann Chem 1975, 1, 160.
2 Das, B.P.; Boykin, D.W.; Synthesis and antiprotozoal activity of 2,5-bis (4-guanylphenyl) furans. J Med Chem 1977, 20, 4, 531-536.
3 Boykin, D.W.; et al.; 2,5-Bis[4-(N-alkylamidino)phenyl]furans as anti-Pneumocystis carinii agents. J Med Chem 1998, 41, 1, 124.
4 Boykin, D.W.; et al.; Anti-pneumocystis activity of bis-amidoximes and bis-O-alkylamidoximes prodrugs. Bioorg Med Chem Lett 1996, 6, 24, 3017.
5 Niigata, K.; Murakami, M.; Kagami, S.; Fujikura, S.; Kojima, A.; Tachikawa, S.; Nozaki, J.; Takahashi, K. (Yamanouchi Pharmaceutical Co., Ltd.); Novel indene derivs. or their salts. JP 1977111580 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 57909 Fumaryl chloride 627-63-4 C4H2Cl2O2 详情 详情
(II) 13365 Monobromobenzene; 1-Bromobenzene;Phenylbromide;bromobenzene 108-86-1 C6H5Br 详情 详情
(III) 57910 (E)-1,4-bis(4-bromophenyl)-2-butene-1,4-dione C16H10Br2O2 详情 详情
(IV) 35811 1,4-bis(4-bromophenyl)-1,4-butanedione C16H12Br2O2 详情 详情
(V) 35812 2,5-bis(4-bromophenyl)furan C16H10Br2O 详情 详情
(VI) 56856 Copper (I) cyanide; Cuprous cyanide 544-92-3 CCuN 详情 详情
(VII) 35814 4-[5-(4-cyanophenyl)-2-furyl]benzonitrile C18H10N2O 详情 详情
(VIII) 35815 ethyl 4-(5-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate C22H22N2O3 详情 详情
Extended Information