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【结 构 式】 
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【分子编号】56433 【品名】methyl (E)-3-[4-(acetyloxy)phenyl]-2-propenoate 【CA登记号】 |
【 分 子 式 】C12H12O4 【 分 子 量 】220.22488 【元素组成】C 65.45% H 5.49% O 29.06% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |