[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl](triphenyl)phosphonium bromide -Drug Synthesis Database

【结构式】

【分子编号】33334

【品名】[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl](triphenyl)phosphonium bromide

【CA登记号】

【分子式】C₃₃H₃₈BrP

【分子量】545.542482

【元素组成】C 72.65% H 7.02% Br 14.65% P 5.68%

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：(III)

The reaction of vinyl-beta-ionol (I) with triphenylphosphonium bromide (II) in ethanol gives the corresponding phosphonium salt (III), which is condensed through a Wittig reaction with cis-beta-formylcrotonic acid (IV) by means of sodium ethoxide in ethanol to afford a mixture of cis-2-cis-4-vitamin A acid (V) and the desired product. Finally, compound (V) is isomerized bv irradiation with diffuse light in ether in the presence of iodine.

参考文献中间体

合成目标

【1】 Garbers, C.F.; et al.; Synthesis of cis-2, cis-4-vitamin A by a Wittig condensation. J Chem Soc 1968, 16, 1982-83.
【2】 Castaner, J.; Serradell, M.N.; Hillier, K.; Blancafort, P.; Isotretinoin. Drugs Fut 1979, 4, 9, 651.

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)	33333	(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-ol	3917-39-3	C₁₅H₂₄O	详情	详情
(III)	33334	[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl](triphenyl)phosphonium bromide		C₃₃H₃₈BrP	详情	详情
(IV)	33335	(Z)-3-methyl-4-oxo-2-butenoic acid		C₅H₆O₃	详情	详情
(V)	32679	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; Retinoic acid	302-79-4	C₂₀H₂₈O₂	详情	详情

Extended Information