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【结 构 式】 
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【分子编号】23190 【品名】3,4-diphenyl-1H-pyrazole 【CA登记号】 |
【 分 子 式 】C15H12N2 【 分 子 量 】220.27376 【元素组成】C 81.79% H 5.49% N 12.72% |
合成路线1
该中间体在本合成路线中的序号：(I)1) The condensation of 3,4-diphenylpyrazole (I) with acrylonitrile (II) by means of benzyl-trimethyl-ammonium hydroxide (Triton B) in dioxane gives 1-(2-cyanoethyl)-3,4-diphenylpyrazole (III), which is then reductocondensed with dimethylamine by means of H2 over Pd/C in ethanol.
| 【1】 Feigenson, M.E.; Hansen, P.E.; Bailey, D.M.; Pearl, J.; DeFelice, A.F.; Hlavac, A.G.; Baizman, E.R.; 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. J Med Chem 1985, 28, 256. |
| 【2】 Bailey, D.M. (Sanofi-Synthelabo); 1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles. US 4182895 . |
| 【3】 Prous, J.; Castaner, J.; Fezolamine fumarate. Drugs Fut 1988, 13, 10, 913. |
合成路线2
该中间体在本合成路线中的序号：(I)2) The condensation of (I) with methyl acrylate (IV) by means of Triton B as before gives methyl 3-(3,4-diphenylpyrazol-1-yl)propionate (V), which is saponified with KOH in refluxing methanol yielding the corresponding free acid (VI). The reaction of (VI) with SOCl2 in refluxing CHCl3 affords the acyl chloride (VII), which is treated with dimethylamine in THF to give N,N-dimethyl-3-(3,4-diphenylpyrazol-1-yl)propionamide (VIII). Finally, this compound is reduced with LiAlH4 in refluxing THF.
| 【1】 Bailey, D.M. (Sanofi-Synthelabo); 1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles. US 4182895 . |
| 【2】 Prous, J.; Castaner, J.; Fezolamine fumarate. Drugs Fut 1988, 13, 10, 913. |
| 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) | 23190 | 3,4-diphenyl-1H-pyrazole | C15H12N2 | 详情 | 详情 | |
| (IV) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (V) | 23194 | methyl 3-(3,4-diphenyl-1H-pyrazol-1-yl)propanoate | C19H18N2O2 | 详情 | 详情 | |
| (VI) | 23195 | 3-(3,4-diphenyl-1H-pyrazol-1-yl)propionic acid | C18H16N2O2 | 详情 | 详情 | |
| (VII) | 23196 | 3-(3,4-diphenyl-1H-pyrazol-1-yl)propanoyl chloride | C18H15ClN2O | 详情 | 详情 | |
| (VIII) | 23197 | 3-(3,4-diphenyl-1H-pyrazol-1-yl)-N,N-dimethylpropanamide | C20H21N3O | 详情 | 详情 |