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【结 构 式】 
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【药物名称】 【化学名称】1-(2,4-Dichlorophenyl)-1-[4-[N-methyl-N-(1-naphthylmethyl)aminomethyl]phenyl]methanone 【CA登记号】 【 分 子 式 】C26H21Cl2NO 【 分 子 量 】434.36937 |
【开发单位】Second Military Medical University (Originator) 【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY |
合成路线1
The intermediate naphthylmethyl amine (IV) was prepared from 1-naphthaldehyde (I) by two related procedures. Reduction of (II) with NaBH4 gave alcohol (II), which was converted to the corresponding chloride with SOCl2 and then condensed with methylamine. Alternatively, condensation of aldehyde (I) with methylamine using TiCl4 as the dehydrating reagent produced aldimine (III), which was then reduced to amine (IV) by means of NaBH4.
| 【1】 Zhou, Y.; Zhang, W.; Li, K.; Jiang, Y.; Li, Y.; Wang, X.; The synthesis and antifungal activity of the substituted naphthalenemethanamines. Chin Journal of Medicinal Chemistry 1999, 9, 7, 7. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 11021 | Methanamine; Methylamine | 74-89-5 | CH5N | 详情 | 详情 | |
| (I) | 12314 | 1-Naphthaldehyde | 66-77-3 | C11H8O | 详情 | 详情 |
| (II) | 35129 | 1-naphthylmethanol | 4780-79-4 | C11H10O | 详情 | 详情 |
| (III) | 35130 | N-[(Z)-1-naphthylmethylidene]methanamine; N-methyl-N-[(Z)-1-naphthylmethylidene]amine | C12H11N | 详情 | 详情 | |
| (IV) | 10108 | N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine | 65473-13-4 | C12H13N | 详情 | 详情 |
合成路线2
2,4-Dichlorobenzoic acid (V) was converted to acid chloride (VI) using SOCl2. Further Friedel-Crafts condensation of (VI) with toluene in the presence of AlCl3 produced benzophenone (VII). Benzylic bromination of (VII) with N-bromosuccinimide gave bromide (VIII). Finally, displacement of the bromine of (VIII) by means of amine (IV) furnished the title compound.
| 【1】 Zhou, Y.; Zhang, W.; Li, K.; Jiang, Y.; Li, Y.; Wang, X.; The synthesis and antifungal activity of the substituted naphthalenemethanamines. Chin Journal of Medicinal Chemistry 1999, 9, 7, 7. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 10108 | N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine | 65473-13-4 | C12H13N | 详情 | 详情 |
| (V) | 33443 | 2,4-dichlorobenzoic carboxylic acid; 2,4-dichlorobenzoic acid | 50-84-0 | C7H4Cl2O2 | 详情 | 详情 |
| (VI) | 35131 | 2,4-dichlorobenzoyl chloride; 2,4-Dichlorophenacylchloride | 89-75-8 | C7H3Cl3O | 详情 | 详情 |
| (VII) | 35132 | (2,4-dichlorophenyl)(4-methylphenyl)methanone | C14H10Cl2O | 详情 | 详情 | |
| (VIII) | 35133 | [4-(bromomethyl)phenyl](2,4-dichlorophenyl)methanone | C14H9BrCl2O | 详情 | 详情 |