N-[(Z)-2-cyano-1-phenylethenyl]-1-methyl-N-phenyl-1H-imidazole-2-carbothioamide | 1415321-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(Z)-2-cyano-1-phenylethenyl]-1-methyl-N-phenyl-1H-imidazole-2-carbothioamide
• 英文别名: N-[(Z)-2-cyano-1-phenylethenyl]-1-methyl-N-phenylimidazole-2-carbothioamide
• CAS: 1415321-79-7
• 化学式: C₂₀H₁₆N₄S
• 分子量: 344.44
• InChiKey: HPJKSBDRTMSQMI-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基咪唑 、 3-苯基丙炔腈 、 硫代异氰酸苯酯 反应 24.0h， 以79%的产率得到N-[(Z)-2-cyano-1-phenylethenyl]-1-methyl-N-phenyl-1H-imidazole-2-carbothioamide
  参考文献：
  名称：

  Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides

  摘要：

  N-(Z)-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst-and solvent-free conditions at room temperature. The reaction proceeds via zwitterion-carbene intermediates which are trapped by isothiocyanates to form the zwitterion with ambident N-S anionic site, which then undergoes stereo- and regioselective migration of the alkenyl moiety.

  DOI：

  10.1055/s-0031-1290442