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【结 构 式】 
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【分子编号】20590 【品名】(E)-4-(3-methoxyphenyl)-3-buten-2-one 【CA登记号】 |
【 分 子 式 】C11H12O2 【 分 子 量 】176.21508 【元素组成】C 74.98% H 6.86% O 18.16% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 3-methoxybenzaldehyde (I) with acetone (II) by means of NaOH gives 1-(3-methoxyphenyl)-1-buten-3-one (III), which is hydrogenated with H2 over Pd/C in methanol yielding 1-(3-methoxyphenyl)-3-butanone (IV). The iodination of (IV) with I2-silver acetate in acetic acid affords 1-(2-iodo-5-methoxyphenyl)-3-butanone (V), which is reductocondensed with methylamine and sodium cyanoborohydride in methanol giving 2-iodo-5-methoxy-N,alpha-dimethylphenylpropanamine (VI). The acylation of (VI) with 3,4-dimethoxyphenylacetyl chloride (VII) by means of triethylamine in dichloromethane yields the corresponding acetamide (VIII), which is reduced with borane-THF complex affording the corresponding tertiary amine (IX), which is finally condensed with phenylacetylene (X) by means of butyllithium in THF.
| 【1】 Carson, J.R. (McNeilab, Inc.); Aralkyl(arylethynyl)aralkyl amines for use as vasodilators and antihypertensives. EP 0146271; ES 8604488; US 4661635 . |
| 【2】 Prous, J.; Castaner, J.; McN-5691. Drugs Fut 1989, 14, 4, 322. |
| 【3】 Carson, J.R.; Almond, H.R.; Brannan, M.D.; et al.; 2-Ethynylbenzenealkanamines. A new class of calcium entry blockers. J Med Chem 1988, 31, 3, 630-6. |
| 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) | 20589 | 3-methoxybenzaldehyde; m-Anisaldehyde | 591-31-1 | C8H8O2 | 详情 | 详情 |
| (II) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
| (III) | 20590 | (E)-4-(3-methoxyphenyl)-3-buten-2-one | C11H12O2 | 详情 | 详情 | |
| (IV) | 20591 | 4-(3-methoxyphenyl)-2-butanone | C11H14O2 | 详情 | 详情 | |
| (V) | 20592 | 4-(2-iodo-5-methoxyphenyl)-2-butanone | C11H13IO2 | 详情 | 详情 | |
| (VI) | 20593 | N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylamine; 4-(2-iodo-5-methoxyphenyl)-N-methyl-2-butanamine | C12H18INO | 详情 | 详情 | |
| (VII) | 20594 | 2-(3,4-dimethoxyphenyl)acetyl chloride | C10H11ClO3 | 详情 | 详情 | |
| (VIII) | 20595 | 2-(3,4-dimethoxyphenyl)-N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylacetamide | C22H28INO4 | 详情 | 详情 | |
| (IX) | 20596 | N-(3,4-dimethoxyphenethyl)-N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylamine; N-(3,4-dimethoxyphenethyl)-4-(2-iodo-5-methoxyphenyl)-N-methyl-2-butanamine | C22H30INO3 | 详情 | 详情 | |
| (X) | 20597 | 1-ethynylbenzene | 536-74-3 | C8H6 | 详情 | 详情 |