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【结 构 式】

【分子编号】56435

【品名】3-(4-Hydroxyphenyl)-1-propanol

【CA登记号】

【 分 子 式 】C9H12O2

【 分 子 量 】152.19308

【元素组成】C 71.03% H 7.95% O 21.03%

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)

4-Hydroxybenzaldehyde (I) was acetylated using Ac2O in pyridine. The resultant 4-(acetyloxy)benzaldehyde (II) was then subjected to a Wadsworth-Emmons condensation with trimethyl phosphonoacetate to afford methyl 4-(acetyloxy)cinnamate (III). After catalytic double bond hydrogenation, the resultant saturated ester (IV) was reduced by LiAlH4 to furnish 3-(4-hydroxyphenyl)-1-propanol (V) –alternatively (V) can be obtained by reduction with LiAlH4 of the propionic acid derivative (VI) (isolated from Asplenium onopteris)-. Methylation of the phenolic hydroxyl group of (V) with iodomethane and K2CO3 in acetone gave the methyl ether (VII). Then, oxidation of alcohol (VII) to 3-(4-methoxyphenyl)propanal (VIII) was accomplished by means of pyridinium chlorochromate.

1 Gonzalez, A.G.; et al.; Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group. J Med Chem 2002, 45, 12, 2358.
2 Bermejo Barrera, J.; Hernandez Silva, M.; Alvarez de Mon, M.; Pivel Ranieri, J.P. (CSIC (Consejo Superior de Investigaciones Cientificas)); Derivs. of p-hydroxy phenyl propionic acid as antiproliferative agents. ES 2160093; WO 0172733 .
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) 13433 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde 123-08-0 C7H6O2 详情 详情
(II) 56432 4-Acetoxybenzaldehyde; p-Acetoxybenzaldehyde; p-Formylphenyl acetate 878-00-2 C9H8O3 详情 详情
(III) 56433 methyl (E)-3-[4-(acetyloxy)phenyl]-2-propenoate C12H12O4 详情 详情
(IV) 56434 methyl 3-[4-(acetyloxy)phenyl]propanoate C12H14O4 详情 详情
(V) 56435 3-(4-Hydroxyphenyl)-1-propanol C9H12O2 详情 详情
(VI) 25691 3-(4-hydroxyphenyl)propionic acid 501-97-3 C9H10O3 详情 详情
(VII) 56436 3-(p-Methoxyphenyl)propanol; 3-(4-Methoxyphenyl)propanol 5406-18-8 C10H14O2 详情 详情
(VIII) 56437 3-(4-methoxyphenyl)propanal C10H12O2 详情 详情
Extended Information