benzoyl-[1-[(E)-(4-bromo-2-thienyl)methylideneamino]-3-butylbenzimidazol-3-ium-2-carbothioyl]azanide | 1289375-03-6

• 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: benzoyl-[1-[(E)-(4-bromo-2-thienyl)methylideneamino]-3-butylbenzimidazol-3-ium-2-carbothioyl]azanide
• 英文别名: N-benzoyl-1-[(E)-(4-bromothiophen-2-yl)methylideneamino]-3-butylbenzimidazol-3-ium-2-carboximidothioate
• CAS: 1289375-03-6
• 化学式: C₂₄H₂₁BrN₄OS₂
• 分子量: 525.493
• InChiKey: ACDPZUUSZWCOLN-CVKSISIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (9ci)-1H-苯并咪唑-1-胺 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 生成 benzoyl-[1-[(E)-(4-bromo-2-thienyl)methylideneamino]-3-butylbenzimidazol-3-ium-2-carbothioyl]azanide
  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%).