N-phenyl-1,3-di(propan-2-yl)imidazol-1-ium-2-carboximidothioate | 938051-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-phenyl-1,3-di(propan-2-yl)imidazol-1-ium-2-carboximidothioate
• CAS: 938051-35-5
• 化学式: C₁₆H₂₁N₃S
• 分子量: 287.429
• InChiKey: CVGAKYPVNWKYPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-1,3-di(propan-2-yl)imidazol-1-ium-2-carboximidothioate 、 丙炔酸乙酯 以 丁酮 为溶剂， 以48%的产率得到ethyl (Z)-4-(iso-propyl)amino-5-(2-ethoxycarbonylvinylthio)-1-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Solvent controlled divergent syntheses of polysubstituted pyrroles and pyrrolo[2,3-b]-1,4-thiazines

  摘要：

  The reaction of 2-imidazolyl carbene-derived 2-arylthiocarbamoyl imidazolium salts with ethyl propiolate proceeded via the solvent dependent tandem [3+2] cycloaddition and subsequent ring transformation processes. While the reaction in butanone yielded 3-amino-2-vinylthiopyrroles as the major products, use of benzene as the solvent led to the predominant formation of pyrrolo[2,3-b][1,4]thiazines. This work disclosed a unique ring transformation of imidazoline-spiro-pyrrolines to pyrFOIO[2,3b][1,4]-thiazines, which provides a simple route to both multifunctional pyrroles and pyrrolo[2,3b][1,4]thiazines that are other-wise difficult to synthesize. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.044