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【结 构 式】 
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【分子编号】32724 【品名】[1,3-Dichloro-6-(trifluoromethyl)-9-phenanthryl]methanol; 1,3-Dichloro-6-trifluoromethyl-9-hydroxymethylphenanthrene 【CA登记号】 |
【 分 子 式 】C16H9Cl2F3O 【 分 子 量 】345.1474696 【元素组成】C 55.68% H 2.63% Cl 20.54% F 16.51% O 4.64% |
合成路线1
该中间体在本合成路线中的序号：(II)The reduction of 1,3-dichloro-6-trifluoromethylphenanthrene-9-carboxylic acid (I) with BH3 in THF gives 1,3-dichloro-6-trifluoromethyl-9-hydroxymethylphenanthrene (II), which is oxidized with lead tetracetate in pyridine to yield 1,3-dichloro-6-trifluoromethylphenanthren-9-carboxaldehyde (III). The reaction of (III) with N,N-dibutylbromoacetamide (IV) by means of Zn in THF affords 1,3-dichloro-6-trifluoromethyl-9-[3-(dibutylamino)-3-oxo-1-hydroxypropyl]phenanthrene (V), which is finally reduced with BH3 as before, and treated with HCl.
| 【1】 Hillier, K.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Halofantrine hydrochloride. Drugs Fut 1980, 5, 11, 547. |
| 【2】 Colwell, W.T.; et al.; Antimalarial arylaminopropanols. J Med Chem 1972, 15, 771-775. |
| 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) | 32723 | 1,3-Dichloro-6-(trifluoromethyl)-9-phenanthrenecarboxylic acid; 1,3-Dichloro-6-trifluoromethylphenanthrene-9-carboxylic acid | C16H7Cl2F3O2 | 详情 | 详情 | |
| (II) | 32724 | [1,3-Dichloro-6-(trifluoromethyl)-9-phenanthryl]methanol; 1,3-Dichloro-6-trifluoromethyl-9-hydroxymethylphenanthrene | C16H9Cl2F3O | 详情 | 详情 | |
| (III) | 32725 | 1,3-Dichloro-6-trifluoromethylphenanthren-9-carboxaldehyde; 1,3-Dichloro-6-(trifluoromethyl)-9-phenanthrenecarbaldehyde | C16H7Cl2F3O | 详情 | 详情 | |
| (IV) | 20685 | 2-Bromo-N,N-dibutylacetamide; N,N-Dibutylbromoacetamide | C10H20BrNO | 详情 | 详情 | |
| (V) | 32726 | 1,3-Dichloro-6-trifluoromethyl-9-[3-(dibutylamino)-3-oxo-1-hydroxypropyl]phenanthrene; N,N-Dibutyl-3-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthryl]-3-hydroxypropanamide | C26H28Cl2F3NO2 | 详情 | 详情 |