(4-Methoxy-phenyl)-(4-methyl-3-vinyl-quinolin-2-yl)-amine | 138387-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (4-Methoxy-phenyl)-(4-methyl-3-vinyl-quinolin-2-yl)-amine
• 英文别名: 3-ethenyl-N-(4-methoxyphenyl)-4-methylquinolin-2-amine
• CAS: 138387-03-8
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: KDTFZYVSACJMDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-Methoxy-phenyl)-[2-((E)-1-methyl-buta-1,3-dienyl)-phenyl]-carbodiimide 以 甲苯 为溶剂， 反应 24.0h， 生成 (4-Methoxy-phenyl)-(4-methyl-3-vinyl-quinolin-2-yl)-amine
  参考文献：
  名称：

  C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives

  摘要：

  Iminophosphoranes 2 derived from o-aminostyrenes react with aryl isocyanates to give the corresponding carbodiimides 13 which by thermal treatment at 160-degrees-C undergo 6-pi-electrocyclization to give quinoline derivatives 14. However, the reaction with styryl isocyanates leads to alpha-carbolines 19 through the intermediate carbodiimides 15 which undergo a tandem intramolecular hetero-Diels-Alder cycloaddition/aromatization process to give 19. Similarly, related alpha-carbolines 20-22 can be obtained from the reaction of iminophosphoranes derived from ortho-substituted anilines containing an unsaturated side chain with styryl isocyanates. Iminophosphorane 6a, derived from o-butadienylaniline, and related 10 and 12 react with aryl isocyanates under the same reaction conditions to give quinindoline derivatives 25-27, respectively. Finally, iminophosphoranes 2 and 6 by reaction with ketenes lead directly to quinolines 32 and benzo[b]carbazoles 33, respectively.

  DOI：

  10.1021/jo00029a026