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【结 构 式】 
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【分子编号】40083 【品名】1-(2,3-dichloro-4-methoxyphenyl)-2-phenyl-2-propen-1-one 【CA登记号】 |
【 分 子 式 】C16H12Cl2O2 【 分 子 量 】307.17548 【元素组成】C 62.56% H 3.94% Cl 23.08% O 10.42% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 2,3-dichloroanisole (I) with phenylacetyl chloride (A) by means of AlCl3 in CS2 gives 2,3-dichloro-4-phenylacetylanisole (II), which by reaction with bis(dimethylamino)methane (B) in acetic anhydride is converted into 2,3-dichloro-4-(2-phenylacryloyl)anisole (III). The cyclization of (III) by means of H2SO4 yields 6,7-dichloro-2-phenyl-5-methoxy-1-indanone (IV), which by demethylation with pyridine hydrochloride at 190 C yields 6,7-dichloro-2-phenyl-5-hydroxy-1-indadone (V). The treatment of the phenol (V) with iodoacetic acid (C) and K2CO3 in acetone affords 6,7-dichloro-2-phenyl-1-oxo-5-indanyloxyacetic acid (VI), which is finally methylated with methyl iodide and NaH in DMF.
| 【1】 Cragoe, E.J. Jr.; Woltersdorf, O.W. Jr. (Merck & Co., Inc.); Substituted indanones. DE 2448454; ES 430900; FR 2247218; GB 1474459 . |
| 【2】 Castaner, J.; Chatterjee, S.S.; MK 196. Drugs Fut 1977, 2, 3, 179. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 14349 | N,N,N,N-tetramethylmethanediamine; tetramethylmethylenediamine;bis(dimethylamino)methane; N-[(dimethylamino)methyl]-N,N-dimethylamine | 51-80-9 | C5H14N2 | 详情 | 详情 |
| (A) | 25890 | 2-phenylacetyl chloride；Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride | 103-80-0 | C8H7ClO | 详情 | 详情 |
| (I) | 40081 | 1,2-dichloro-3-methoxybenzene; 2,3-dichlorophenyl methyl ether | 1984-59-4 | C7H6Cl2O | 详情 | 详情 |
| (II) | 40082 | 1-(2,3-dichloro-4-methoxyphenyl)-2-phenyl-1-ethanone | C15H12Cl2O2 | 详情 | 详情 | |
| (III) | 40083 | 1-(2,3-dichloro-4-methoxyphenyl)-2-phenyl-2-propen-1-one | C16H12Cl2O2 | 详情 | 详情 | |
| (IV) | 40084 | 6,7-dichloro-5-methoxy-2-phenyl-1-indanone | C16H12Cl2O2 | 详情 | 详情 | |
| (V) | 40085 | 6,7-dichloro-5-hydroxy-2-phenyl-1-indanone | C15H10Cl2O2 | 详情 | 详情 | |
| (VI) | 40087 | 2-[(6,7-dichloro-1-oxo-2-phenyl-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid | C17H12Cl2O4 | 详情 | 详情 | |
| (C) | 40086 | 2-iodoacetic acid | 64-69-7 | C2H3IO2 | 详情 | 详情 |