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【结 构 式】 
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【药物名称】Diacetolol hydrochloride, M&B-16942A, EU-4891 【化学名称】N-[3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide hydrochloride 【CA登记号】69796-04-9, 22568-64-5 (free base) 【 分 子 式 】C16H25ClN2O4 【 分 子 量 】344.84165 |
【开发单位】 【药理作用】 |
合成路线1
The acetylation of 4-acetamidophenol (I) with acetyl chloride in refluxing benzene gives 4-acetoxyacetanilide (II), which by a Fries reaction with AlCl3 at 170 C is converted into 2-hydroxy-5-acetamidoacetophenone (III). (1,2) The reaction of (III) with epichlorohydrin (IV) by means of sodium ethoxide in refluxing ethanol affords 1-(2-acetyl-4-acetamidophenoxy)-2,3-epoxypropane (V), which is finally treated with isopropylamine (VI) in refluxing ethanol. (1-3)
| 【1】 Woolbridge, K.R.H.; Basil, B (May & Baker, Ltd.); ZA 6808345 . |
| 【2】 Basil, B.; et al.; New series of cardioselective adrenergic beta-receptor blocking compounds. 1-(2-Acyl-4-acylaminophenoxy)3-isopropylaminopropan-2-ols. J Med Chem 1976, 19, 3, 399. |
| 【3】 Woolbridge, K.R.H.; Basil, B. (May & Baker, Ltd.); BE 715205; CA 834734; CH 485663; CH 489467; FR 1570087; FR M7616; GB 1231783; GB 681537; JP 7134414; NL 6806946; ZA 6803130 . |
| 【4】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Weetman, D.F.; Diacetolol hydrochloride. Drugs Fut 1981, 6, 8, 467. |
| 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) | 21611 | 4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide | 103-90-2 | C8H9NO2 | 详情 | 详情 |
| (II) | 60980 | 4-(acetylamino)phenyl acetate | C10H11NO3 | 详情 | 详情 | |
| (III) | 21612 | N-(3-acetyl-4-hydroxyphenyl)acetamide | C10H11NO3 | 详情 | 详情 | |
| (IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (V) | 60981 | N-[3-acetyl-4-(2-oxiranylmethoxy)phenyl]acetamide | C13H15NO4 | 详情 | 详情 | |
| (VI) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
Extended Information