1-[(E)-benzylideneamino]-3-butylbenzimidazol-3-ium-2-carbodithioate | 1289374-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-[(E)-benzylideneamino]-3-butylbenzimidazol-3-ium-2-carbodithioate
• CAS: 1289374-96-4
• 化学式: C₁₉H₁₉N₃S₂
• 分子量: 353.512
• InChiKey: XBUWSSAADOMXQE-XSFVSMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-N-(benzimidazol-1-yl)-1-phenyl-methanimine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 1-[(E)-benzylideneamino]-3-butylbenzimidazol-3-ium-2-carbodithioate
  参考文献：
  名称：

  Carbene-Mediated Transformations of 1-(Benzylideneamino)benzimidazoles

  摘要：

  Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).

  DOI：

  10.1021/jo200088s

文献信息

• Carbene-Mediated Transformations of 1-(Benzylideneamino)benzimidazoles
  作者：Alan R. Katritzky、Davit Jishkariani、Rajeev Sakhuja、C. Dennis Hall、Peter J. Steel

  DOI：10.1021/jo200088s

  日期：2011.5.20

  Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).