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【结 构 式】

【分子编号】13261

【品名】methyl (2E,4E)-5-(4-methoxyphenyl)-2,4-decadienoate

【CA登记号】

【 分 子 式 】C18H24O3

【 分 子 量 】288.38676

【元素组成】C 74.97% H 8.39% O 16.64%

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:(V)

A) Synthesis of intermediate (VII): The hexanophenone (I), prepared by Freidel-Crafts acylation of anisole with hexanoyl chloride, was condensed with lithioacetonitrile to generate the carbinol (II), which was then dehydrated using trifluoroacetic acid in dichloromethane to produce the unsaturated nitrile (III) predominantly as its (E)-isomer (E/Z ratio > 12:1). Reduction of the newly formed alpha,beta-unsaturated nitrile with diisobutylaluminum hydride furnished the (E)-octenal (IV), which was then treated with the stabilized ylid (carbomethoxymethylene)triphenylphosphorane to yield the dienoic acid ester (V). While use of a polar reaction medium such as methanol or ethanol in this Wittig reaction resulted in mixtures of isomers with an E/Z ratio as high as 3:2 around the newly introduced double bond, formation of the (Z)-isomer could be minimized (< 7%) through the use of an aprotic reaction solvent, e.g., dichloromethane or benzene. In preparation for its conversion to the target carboxamide, the (E,E)-decadienoic acid ester was saponified and the resulting acid (VI) condensed with p-nitrophenol in the presence of dicyclohexylcarbodiimide to yield the highly reactive p-nitrophenyl ester (VII).

1 Vargaftig, B.B.; Benveniste, J.; Lefort, J.; Wal, F.; Chignard, M.; Background and present status of research on platelet-activating factor (PAF-acether). Ann NY Acad Sci 1981, 370, 119-37.
2 D'Donnell, M.; Kierstead, R.W.; Guthrie, R.W.; Tilley, J.W.; Ro 24-0238. Drugs Fut 1991, 16, 12, 1103.
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) 13257 1-(4-Methoxyphenyl)-1-hexanone C13H18O2 详情 详情
(II) 13258 3-Hydroxy-3-(4-methoxyphenyl)octanenitrile C15H21NO2 详情 详情
(III) 13259 (E)-3-(4-Methoxyphenyl)-2-octenenitrile C15H19NO 详情 详情
(IV) 13260 (E)-3-(4-Methoxyphenyl)-2-octenal C15H20O2 详情 详情
(V) 13261 methyl (2E,4E)-5-(4-methoxyphenyl)-2,4-decadienoate C18H24O3 详情 详情
(VI) 13262 (2E,4E)-5-(4-Methoxyphenyl)-2,4-decadienoic acid C17H22O3 详情 详情
(VII) 13263 4-nitrophenyl (2E,4E)-5-(4-methoxyphenyl)-2,4-decadienoate C23H25NO5 详情 详情
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