C-Cyclohexyl-C-(5-methyl-2-phenyl-1-p-tolyl-1H-pyrrol-3-yl)-methyleneamine | 1027400-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: C-Cyclohexyl-C-(5-methyl-2-phenyl-1-p-tolyl-1H-pyrrol-3-yl)-methyleneamine
• 英文别名: Cyclohexyl-[5-methyl-1-(4-methylphenyl)-2-phenylpyrrol-3-yl]methanimine
• CAS: 1027400-45-8
• 化学式: C₂₅H₂₈N₂
• 分子量: 356.511
• InChiKey: HACWLDWRPOLUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  28.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-Cyclohexyl-C-(5-methyl-2-phenyl-1-p-tolyl-1H-pyrrol-3-yl)-methyleneamine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 3-(aminocyclohexylmethyl)-5-methyl-2-phenyl-1-(p-tolyl)pyrrole
  参考文献：
  名称：

  An Efficient Approach to Pyrroles and N-Bridgehead Pyrroles by Propargylation/Cycloamination of 4-Amino-1-azabutadiene Derivatives

  摘要：

  The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.

  DOI：

  10.1021/jo951887y
• 作为产物：
  描述：

  [(E)-2-(Cyclohexyl-imino-methyl)-1-phenyl-pent-1-en-4-ynyl]-p-tolyl-amine 以 甲苯 为溶剂， 反应 4.0h， 生成 C-Cyclohexyl-C-(5-methyl-2-phenyl-1-p-tolyl-1H-pyrrol-3-yl)-methyleneamine
  参考文献：
  名称：

  An Efficient Approach to Pyrroles and N-Bridgehead Pyrroles by Propargylation/Cycloamination of 4-Amino-1-azabutadiene Derivatives

  摘要：

  The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.

  DOI：

  10.1021/jo951887y