1,5-Dimethyl-3-phenylethynyl-1H-pyrazole-4-carboxylic acid amide | 133053-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-Dimethyl-3-phenylethynyl-1H-pyrazole-4-carboxylic acid amide
• 英文别名: 1,5-dimethyl-3-(2-phenylethynyl)pyrazole-4-carboxamide
• CAS: 133053-65-3
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: RQTHJDGJACQIIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-Dimethyl-3-phenylethynyl-1H-pyrazole-4-carboxylic acid amide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 42.0h， 以70%的产率得到2,3-dimethyl-6-phenyl-2,5-dihydropyrazolo[4,3-c]pyridin-4-one
  参考文献：
  名称：

  Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

  摘要：

  Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or five-membered lactam ring. The formation of a gamma-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

  DOI：

  10.1007/bf00958258
• 作为产物：
  描述：

  copper(I) phenylacetylenide 、 3-Iodo-1,5-dimethylpyrazole-4-carbonamide 在 吡啶 作用下， 反应 6.0h， 以62%的产率得到1,5-Dimethyl-3-phenylethynyl-1H-pyrazole-4-carboxylic acid amide
  参考文献：
  名称：

  Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

  摘要：

  Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or five-membered lactam ring. The formation of a gamma-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

  DOI：

  10.1007/bf00958258

文献信息

• VASILEVSKIJ, S. F.;SHVARTSBERG, M. S., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2089-2093
  作者：VASILEVSKIJ, S. F.、SHVARTSBERG, M. S.

  DOI：——

  日期：——