(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-ol -Drug Synthesis Database

【结构式】

【分子编号】33333

【品名】(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-ol

【CA登记号】3917-39-3

【分子式】C₁₅H₂₄O

【分子量】220.35496

【元素组成】C 81.76% H 10.98% O 7.26%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

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

合成路线2

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Wada A, Fukunaga K, Ito M, et aL. 2004. Preparation and biological activity of 13-substituted retinoic acids. Bioorg Med Chem, 12 (14): 393～3942

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	65481	(2E,4E)-3-Methyl-5-(2,6,6-Trimethyl-1-Cyclohexenyl)Penta-2,4-Dienal	1209-68-3	C₁₅H₂₂O	详情	详情
(I)	66898	(E)-1,3,3-trimethyl-2-(3-((trifluoromethyl)sulfonyl)prop-1-en-1-yl)cyclohex-1-ene		C₁₃H₁₉F₃O₂S	详情	详情
(II)	66899	(E)-3-(tributylstannyl)but-2-en-1-ol		C₁₆H₃₄OSn	详情	详情
(III)	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
(VI)	66900	1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-yn-1-yl)cyclohex-1-ene		C₁₆H₂₂	详情	详情
(VII)	66901	(2E,4E,6E,8E)-ethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate		C₂₂H₃₂O₂	详情	详情

Extended Information