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【结 构 式】 
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【分子编号】40178 【品名】(E)-2-Butenoyl chloride; (E)-Crotonyl chloride 【CA登记号】625-35-4 |
【 分 子 式 】C4H5ClO 【 分 子 量 】104.5358 【元素组成】C 45.96% H 4.82% Cl 33.91% O 15.31% |
合成路线1
该中间体在本合成路线中的序号：(VII)The Friedel-Crafts reaction of anisole (VI) with crotonyl chloride (VII) by means of AlCl3 in carbon disulfide gives p-methoxyphenyl propenyl ketone (VIII), which is then condensed with homoveratrylamine (IV) in toluene yielding 3-(3,4-dimethoxyphenylethylamino)-1-(4-methoxyphenyl)butan-1-one (IX). Finally, this ketone is reduced with hydrogen over Pd/C in ethanol to yield 3,4-dimethoxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-beta-phenylethylamine (I), which by demethylation with HBr in refluxing acetic acid.
| 【1】 Castaner, J.; Thorpe, P.; Dobutamine. Drugs Fut 1977, 2, 9, 579. |
| 【2】 Tuttle, R.R.; Mills, J. (Eli Lilly and Company); Dopamine derivatives. DE 2317710; ES 413639; FR 2182947; GB 1392674; JP 49007237 . |
| 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) | 40177 | N-(3,4-dimethoxyphenethyl)-4-(4-methoxyphenyl)-2-butanamine; N-(3,4-dimethoxyphenethyl)-N-[3-(4-methoxyphenyl)-1-methylpropyl]amine | C21H29NO3 | 详情 | 详情 | |
| (IV) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (VI) | 23767 | Methoxybenzene; Methyl phenyl ether; Anisole | 100-66-3 | C7H8O | 详情 | 详情 |
| (VII) | 40178 | (E)-2-Butenoyl chloride; (E)-Crotonyl chloride | 625-35-4 | C4H5ClO | 详情 | 详情 |
| (VIII) | 40179 | (E)-1-(4-methoxyphenyl)-2-buten-1-one | C11H12O2 | 详情 | 详情 | |
| (IX) | 40180 | 3-[(3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-butanone | C21H27NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The title N-acyloxazolidinone is synthesized by condensation of E-crotonyl chloride (I) with the lithium derivative of (S)-4-benzyl-2-oxazolidinone (II) in cold THF.
| 【1】 McHenry, K.T.; Ankala, S.V.; Ghosh, A.K.; Fenteany, G.; A non-antibacterial oxazolidinone derivative that inhibits epithelial cell sheet migration. ChemBioChem 2002, 3, 11, 1105. |