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【结 构 式】 
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【分子编号】43656 【品名】1-(4-[2-hydroxy-3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy]phenyl)acetone 【CA登记号】 |
【 分 子 式 】C23H30N2O4 【 分 子 量 】398.50228 【元素组成】C 69.32% H 7.59% N 7.03% O 16.06% |
合成路线1
该中间体在本合成路线中的序号：(VI)The demethylation of 1-(4-methoxyphenyl)acetone (I) by means of AlCl3 gives the corresponding 4-hydroxy compound (III), which is condensed with epichlorohydrin (III), yielding the expected oxiranylmethyl ether (IV). The addition of 1-(2-methoxyphenyl)piperazine (V) to the epoxide ring of (IV) affords the isopropyl alcohol derivative (VI), which is condensed with dimethylformamide dimethylacetal (VII) to afford the dimethylaminobutenone (VIII). Finally, this compound is cyclized with 2-cyanoacetamide (IX) by means of sodium ethoxide, providing the target pyridone.
| 【1】 (Beiersdorf-Lilly GmbH); Phenylpiperazinylpropanol derivs.. DE 3424685; EP 0167121; ES 8608511; JP 1986030573; US 4631279; US 4631281 . |
| 【2】 Armah, B.I.; Stenzel, W.; SATERINONE (BDF 8634): A DIFFERENT CONCEPT FOR PHARMACOTHERAPY OF CONGESTIVE HEART FAILURE. Drugs Fut 1989, 14, 5, 445. |
| 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) | 10038 | 4-Methoxyphenylacetone; 1-(4-Methoxyphenyl)acetone | 122-84-9 | C10H12O2 | 详情 | 详情 |
| (II) | 43654 | 1-(4-hydroxyphenyl)acetone | C9H10O2 | 详情 | 详情 | |
| (III) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 43655 | 1-[4-(2-oxiranylmethoxy)phenyl]acetone | C12H14O3 | 详情 | 详情 | |
| (V) | 11882 | 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine | 35386-24-4 | C11H16N2O | 详情 | 详情 |
| (VI) | 43656 | 1-(4-[2-hydroxy-3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy]phenyl)acetone | C23H30N2O4 | 详情 | 详情 | |
| (VII) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (VIII) | 43657 | (Z)-4-(dimethylamino)-3-(4-[2-hydroxy-3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy]phenyl)-3-buten-2-one | C26H35N3O4 | 详情 | 详情 | |
| (IX) | 12122 | Cyanoacetamide; 2-Cyanoacetamide | 107-91-5 | C3H4N2O | 详情 | 详情 |