1-tert-Butyl-5-tert-butylamino-3-(2,6-dimethyl-phenyl)-2-methylsulfanyl-4-phenyl-3H-imidazol-1-ium; chloride | 138877-77-7

• 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-tert-Butyl-5-tert-butylamino-3-(2,6-dimethyl-phenyl)-2-methylsulfanyl-4-phenyl-3H-imidazol-1-ium; chloride
• 英文别名: N,3-ditert-butyl-1-(2,6-dimethylphenyl)-2-methylsulfanyl-5-phenylimidazol-3-ium-4-amine;chloride
• CAS: 138877-77-7
• 化学式: C₂₆H₃₆N₃S*Cl
• 分子量: 458.111
• InChiKey: DBECPLYAQAZKSD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 以 氯仿 为溶剂， 生成 1-tert-Butyl-5-tert-butylamino-3-(2,6-dimethyl-phenyl)-2-methylsulfanyl-4-phenyl-3H-imidazol-1-ium; chloride
  参考文献：
  名称：

  Three-component cyclocondensations. An efficient synthesis of 4-amino-2-(methylthio)imidazolium salts via the reaction of methyl chlorothioimidates with benzaldimines and isocyanides. Autoxidation of the imidazole derivatives

  摘要：

  Treatment of imino chlorosulfides 1 with a mixture of benzaldimine and isocyanide provides 4-aminoimidazolium chlorides 5. Presumably this reaction involves the N-imidoylbenzylideniminium chlorides 4 as transient intermediates. 1- and 3-tert-Butyl imidazolium salts 5 undergo fast isobutene elimination giving the corresponding imidazole and imidazoline hydrochlorides 10 and 13. Compounds 13 autoxidize to afford 5-hydroxy derivatives 14 under atmospheric oxygen. The structural assignment of 14 has been confirmed by X-ray diffraction analysis. Under similar conditions, treatment of ketimines 17 with methyl chlorothioimidate 1 and isocyanide gives 2-thioxodiazolidines 19.

  DOI：

  10.1021/jo00033a038