5-Vinyl-11H-10,11-diaza-benzo[b]fluorene | 132606-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-Vinyl-11H-10,11-diaza-benzo[b]fluorene
• 英文别名: 11-ethenyl-6H-indolo[2,3-b]quinoline
• CAS: 132606-69-0
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: KSGNKNRZZFJLHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N'-[2-[(1E)-buta-1,3-dienyl]phenyl]-N-phenylmethanediimine 以 甲苯 为溶剂， 反应 16.0h， 以39%的产率得到5-Vinyl-11H-10,11-diaza-benzo[b]fluorene
  参考文献：
  名称：

  碳二亚胺的环加成反应。CC共轭碳二亚胺分子内Diels-Alder反应的第一个例子

  摘要：

  描述了一种基于串联的分子内Diels-Alder环加成/氧化芳构化反应的共轭碳二亚胺单罐制备α-咔啉和喹啉的方法。

  DOI：

  10.1039/c39900001277

文献信息

• Cycloaddition reactions of carbodiimides. The first example of an intramolecular Diels–Alder reaction of CC-conjugated carbodiimides
  作者：Pedro Molina、Mateo Alajarín、Angel Vidal

  DOI：10.1039/c39900001277

  日期：——

  An one-pot preparation of α-carbolines and quinindolines from conjugated carbodiimides based on a tandem Intramolecular Diels–Alder cycloaddition/oxidative aromatization is described.

  描述了一种基于串联的分子内Diels-Alder环加成/氧化芳构化反应的共轭碳二亚胺单罐制备α-咔啉和喹啉的方法。
• MOLINA, PEDRO;ALAJARIN, MATEO;VIDAL, ANGEL, J. CHEM. SOC. CHEM. COMMUN.,(1990) N8, C. 1277-1279
  作者：MOLINA, PEDRO、ALAJARIN, MATEO、VIDAL, ANGEL

  DOI：——

  日期：——
• C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal、Pilar Sanchez-Andrada

  DOI：10.1021/jo00029a026

  日期：1992.1

  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.