1-dimethylsulfamoyl-5-phenylazoimidazole | 1367346-15-3

• 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-dimethylsulfamoyl-5-phenylazoimidazole
• CAS: 1367346-15-3
• 化学式: C₁₁H₁₃N₅O₂S
• 分子量: 279.323
• InChiKey: BBWKXYGRJZTVTI-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-dimethylsulfamoyl-5-phenylazoimidazole 在 盐酸 、 水 、 三乙胺 作用下， 以 acetontrile 、 乙醇 为溶剂， 反应 6.0h， 生成 1-trityl-4-phenylazoimidazole
  参考文献：
  名称：

  Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with Benzenediazonium Salts

  摘要：

  In contrast to azobenzenes, heterocyclic azo compounds are less well investigated. Phenylazoimidazoles would be versatile as photodissociable ligands (PDLs) because imidazole is an important donor in coordination chemistry. Here, we present the synthesis of 4- and 5-phenylazoimidazoles via a novel azo-coupling method. 1,2-Protected imidazole is lithiated in the 5-position and coupled with benzenediazonium tetrafluoroborate. Several new phenylazoimidazoles were prepared. They exhibit an excellent switching behavior. Upon irradiation of the trans isomers with UV light, >95% of the cis forms are obtained. Upon heating, a complete transformation back to the trans configuration was achieved. Back switching with visible light, however, is incomplete.

  DOI：

  10.1021/jo202688x
• 作为产物：
  描述：

  N,N-二甲基咪唑-1-磺酰胺 在 正丁基锂 、 四丁基氟化铵 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 35.0h， 生成 1-dimethylsulfamoyl-5-phenylazoimidazole
  参考文献：
  名称：

  Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with Benzenediazonium Salts

  摘要：

  In contrast to azobenzenes, heterocyclic azo compounds are less well investigated. Phenylazoimidazoles would be versatile as photodissociable ligands (PDLs) because imidazole is an important donor in coordination chemistry. Here, we present the synthesis of 4- and 5-phenylazoimidazoles via a novel azo-coupling method. 1,2-Protected imidazole is lithiated in the 5-position and coupled with benzenediazonium tetrafluoroborate. Several new phenylazoimidazoles were prepared. They exhibit an excellent switching behavior. Upon irradiation of the trans isomers with UV light, >95% of the cis forms are obtained. Upon heating, a complete transformation back to the trans configuration was achieved. Back switching with visible light, however, is incomplete.

  DOI：

  10.1021/jo202688x