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【结 构 式】 
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【分子编号】36491 【品名】3-(4-chlorophenyl)-4-(1H-pyrrol-1-yl)butyric acid 【CA登记号】 |
【 分 子 式 】C14H14ClNO2 【 分 子 量 】263.7234 【元素组成】C 63.76% H 5.35% Cl 13.44% N 5.31% O 12.13% |
合成路线1
该中间体在本合成路线中的序号：(III)The cyclization of the amino group of 4-amino-3-(4-chlorophenyl)butyric acid (I) with 2,5-dimethoxytetrahydrofuran (II) by means of AcOH in THF gives the corresponding pyrrole (III), which is cyclized by means of TEA, ClCOOEt, pyrrolidine and POCl3 in toluene yielding the pyrrolopyridone (IV). Finally, this compound is condensed with pyridine-4-carbaldehyde (V) by means of tetrabutylammonium bisulfate and NaOH in water.
| 【1】 Moslemi, S.; Dallemagne, P.; Enguehard, C.; Sonnet, P.; Séralini, G.-E.; Bureau, R.; Auvray, P.; Sourdaine, P.; Guillon, J.; Rault, S.; MR 20492 and MR 20494: Two indolizinone derivatives that strongly inhibit human aromatase. J Steroid Biochem Mol Biol 1999, 70, 1-3, 59. |
| 【2】 Sonnet, P.; Dallemagne, P.; Guillon, J.; et al.; New aromatase inhibitors. Synthesis and biological activity of aryl-substituted pyrrolizine and indolizine derivatives. Bioorg Med Chem 2000, 8, 5, 945. |
| 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) | 36490 | 4-amino-3-(4-chlorophenyl)butyric acid | 1134-47-0 | C10H12ClNO2 | 详情 | 详情 |
| (II) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (III) | 36491 | 3-(4-chlorophenyl)-4-(1H-pyrrol-1-yl)butyric acid | C14H14ClNO2 | 详情 | 详情 | |
| (IV) | 18742 | 6-(4-chlorophenyl)-6,7-dihydro-8(5H)-indolizinone | C14H12ClNO | 详情 | 详情 | |
| (V) | 17203 | 4-Pyridinecarboxaldehyde; isonicotinaldehyde | 872-85-5 | C6H5NO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The cyclization of the amino group of 4-amino-3-(4-chlorophenyl)butyric acid (I) with 2,5-dimethoxytetrahydrofuran (II) by means of AcOH in THF gives the corresponding pyrrole (III), which is cyclized by means of TEA, ClCOOEt, pyrrolidine and POCl3 in toluene yielding the pyrrolopyridone (IV). Finally, this compound is condensed with pyridine-3-carbaldehyde (V) by means of tetrabutylammonium bisulfate and NaOH in water.
| 【1】 Moslemi, S.; Dallemagne, P.; Enguehard, C.; Sonnet, P.; Séralini, G.-E.; Bureau, R.; Auvray, P.; Sourdaine, P.; Guillon, J.; Rault, S.; MR 20492 and MR 20494: Two indolizinone derivatives that strongly inhibit human aromatase. J Steroid Biochem Mol Biol 1999, 70, 1-3, 59. |
| 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) | 36490 | 4-amino-3-(4-chlorophenyl)butyric acid | 1134-47-0 | C10H12ClNO2 | 详情 | 详情 |
| (II) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (III) | 36491 | 3-(4-chlorophenyl)-4-(1H-pyrrol-1-yl)butyric acid | C14H14ClNO2 | 详情 | 详情 | |
| (IV) | 18742 | 6-(4-chlorophenyl)-6,7-dihydro-8(5H)-indolizinone | C14H12ClNO | 详情 | 详情 | |
| (V) | 12849 | Nicotinaldehyde; 3-Pyridinecarboxaldehyde | 500-22-1 | C6H5NO | 详情 | 详情 |