1,3-Diisopropyl-2-(methylthio)-5-(4-nitrophenyl)-4-(isopropylamino)imidazolium chloride | 138877-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-Diisopropyl-2-(methylthio)-5-(4-nitrophenyl)-4-(isopropylamino)imidazolium chloride
• 英文别名: 2-methylsulfanyl-5-(4-nitrophenyl)-N,1,3-tri(propan-2-yl)imidazol-3-ium-4-amine;chloride
• CAS: 138877-91-5
• 化学式: C₁₉H₂₉N₄O₂S*Cl
• 分子量: 412.984
• InChiKey: FUJAOTBIEDUPTM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.98
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  异氰化异丙酯 、 isopropyl-p-nitrobenzylideneamine 、 Carbonochloridimidothioic acid, (1-methylethyl)-, methyl ester 以 氯仿 为溶剂， 反应 168.0h， 以66%的产率得到1,3-Diisopropyl-2-(methylthio)-5-(4-nitrophenyl)-4-(isopropylamino)imidazolium 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