【结 构 式】 |
【分子编号】29357 【品名】1-(2-chloroethoxy)-4-[(E)-3,3,3-trifluoro-1,2-diphenyl-1-propenyl]benzene 【CA登记号】 |
【 分 子 式 】C23H18ClF3O 【 分 子 量 】402.8432296 【元素组成】C 68.58% H 4.5% Cl 8.8% F 14.15% O 3.97% |
合成路线1
该中间体在本合成路线中的序号:(X)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 |