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【结 构 式】

【分子编号】29356

【品名】1-(2-chloroethoxy)-4-(3,3,3-trifluoro-1,2-diphenylpropyl)benzene

【CA登记号】

【 分 子 式 】C23H20ClF3O

【 分 子 量 】404.8591096

【元素组成】C 68.23% H 4.98% Cl 8.76% F 14.08% O 3.95%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

The synthesis of GYKI-13504 is as follows: Trifluoroacetophenone (I) is reacted with triphenylbenzyl phosphonium chloride (II) in the presence of sodium methylate and this reaction yields stilbene (III). Stilbene (III) is then hydrogenized in the presence of charcoal palladium catalyzer and the yielded propane derivative (IV) is brominated with 1,2-dibromoethane. The brominated compound (V) is reacted with anizole (A) according to the Friedel Crafts' reaction. The yield (VI) is treated with pyridine hydrochloride and the phenol derivative (VII) is reacted with 2-chloroethanol tosylate (VIII) in the presence of potassium hydroxide. The chloroethoxy (IX) is treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and the (E)-isomer (X) is obtained with fractionated crystallization. This latter product is reacted with 2-aminoethanol (B) to obtain the end product GYKI-13504.

1 Abraham, G.; Horváth, T.; Toldy, L.; Borvendeg, J.; Csányl, E.; Kiss, E.; Szente, I.; Tory, K. (Egis Pharmaceuticals Ltd.); 1,1,2-Triphenylpropane and -propene derivatives. AT 368989; BE 0884716; DD 152536; ES 494286; GB 2058061; GR 69821; HU 18253 .
2 Borvendeg, J.; GYKI-13504. Drugs Fut 1985, 10, 5, 395.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(A) 23767 Methoxybenzene; Methyl phenyl ether; Anisole 100-66-3 C7H8O 详情 详情
(I) 29349 2,2,2-trifluoro-1-phenyl-1-ethanone; 4-Chloro-2-fluorotrifluoroacetophenone 434-45-7 C8H5F3O 详情 详情
(II) 42794 Benzyl(triphenyl)phosphonium chloride 1449-46-3 C25H22ClP 详情 详情
(III) 29351 1-[(Z)-3,3,3-trifluoro-2-phenyl-1-propenyl]benzene C15H11F3 详情 详情
(IV) 29352 1-(3,3,3-trifluoro-2-phenylpropyl)benzene C15H13F3 详情 详情
(V) 29353 1-(1-bromo-3,3,3-trifluoro-2-phenylpropyl)benzene C15H12BrF3 详情 详情
(VI) 29354 1-methoxy-4-(3,3,3-trifluoro-1,2-diphenylpropyl)benzene C22H19F3O 详情 详情
(VII) 29355 4-(3,3,3-trifluoro-1,2-diphenylpropyl)phenol C21H17F3O 详情 详情
(VIII) 14632 2-chloroethyl 4-methylbenzenesulfonate; 2-Chloroethyl-p-toluenesulfonate 80-41-1 C9H11ClO3S 详情 详情
(IX) 29356 1-(2-chloroethoxy)-4-(3,3,3-trifluoro-1,2-diphenylpropyl)benzene C23H20ClF3O 详情 详情
(X) 29357 1-(2-chloroethoxy)-4-[(E)-3,3,3-trifluoro-1,2-diphenyl-1-propenyl]benzene C23H18ClF3O 详情 详情
Extended Information