3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】39591

【品名】3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate

【CA登记号】

【分子式】C₂₂H₃₀O₃

【分子量】342.4784

【元素组成】C 77.16% H 8.83% O 14.01%

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：(XVI)

The reaction of vitamin A aldehyde (retinene) (XV) with NBS and acetic acid - acetic anhydride in CHCl3 gives 3-acetoxyretinene (XVI), which is reduced with NaBH4 in methanol to yield 3-acetoxyretinol (XVII). The reaction of (XVII) with triphenylphosphine and HCl in methanol affords 3-acetoxyretinyltriphenylphosphonium chloride (XVIII), which is condensed through a Wittig reaction with aldehyde (XVI) by means of sodium methoxide in isopropanol giving trans-isozeaxanthin (XIX). Finally, this compound is oxidized with aluminum isopropoxide in refluxing benzene - acetone.

参考文献中间体

合成目标

【1】 Surmatis, J.D.; et al.; Synthesis of oxygenated carotenoids. Helv Chim Acta 1970, 53, 5, 974-990.
【2】 Surmatis, J.D.; US 3311656 .
【3】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XV)	39590	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal	C₂₀H₂₈O	详情	详情
(XVI)	39591	3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate	C₂₂H₃₀O₃	详情	详情
(XVII)	39592	3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethyl-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate	C₂₂H₃₂O₃	详情	详情
(XVIII)	39593	[(2E,4E,6E,8E)-9-[3-(acetoxy)-2,6,6-trimethyl-1-cyclohexen-1-yl]-3,7-dimethyl-2,4,6,8-nonatetraenyl](triphenyl)phosphonium chloride	C₄₀H₄₆ClO₂P	详情	详情
(XIX)	39594	3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2,4,4-trimethyl-2-cyclohexen-1-ol	C₄₀H₅₆O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVI)

The reduction of retinene (XV) with NaBH4 in methanol gives retinol (XX), which by reaction with triphenylphosphine and H2SO4 is converted into retinyltriphenylphosphonium sulfate (XXI). The Wittig reaction of (XXI) with aldehyde (XVI) by means of sodium methoxide in benzene - methanol yields 3-acetylisocryptoxanthin (XXII), which by reaction with aqueous 68% HBr in methylene chloride, followed by a treatment with Na2CO3 affords dehydro-retro-carotene (XXIII).

参考文献中间体

合成目标

【1】 Surmatis, J.D.; et al.; Synthesis of oxygenated carotenoids. Helv Chim Acta 1970, 53, 5, 974-990.
【2】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	39590	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal		C₂₀H₂₈O	详情	详情
(XVI)	39591	3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate		C₂₂H₃₀O₃	详情	详情
(XX)	39595	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol	68-26-8	C₂₀H₃₀O	详情	详情
(XXI)	39596	[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl](triphenyl)phosphonium hydrogen sulfate		C₃₈H₄₅O₄PS	详情	详情
(XXII)	39597	2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2-cyclohexen-1-yl acetate		C₄₂H₅₈O₂	详情	详情
(XXIII)	39598	1,5,5-trimethyl-6-[(Z,2E,4E,6E,8E,10E,12E,14E,16E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2,4,6,8,10,12,14,16-octadecaoctaenylidene]-1-cyclohexene		C₄₀H₅₄	详情	详情

Extended Information