methyl 3-phenyl-9H-pyrido[2,3-b]indole-4-carboxylate | 138386-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 3-phenyl-9H-pyrido[2,3-b]indole-4-carboxylate
• CAS: 138386-83-1
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: PRFGBOABTMKUGL-UHFFFAOYSA-N

物化性质

• 沸点：
  540.7±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-{2-[(triphenylphosphoranylidene)amino]phenyl}-propenoic acid methyl ester 在 manganese(IV) oxide 作用下， 以 xylene 为溶剂， 反应 1.0h， 生成 methyl 3-phenyl-9H-pyrido[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  Conjugated heterocumulenes. Synthesis of conjugated carbodiimides and their facile conversion via intramolecular cycloaddition into nitrogen heterocycles, quinoline and pyrido[2,3-b]indole (α-carboline) derivatives

  摘要：

  描述了一种便捷的方法用于合成共轭卡宾二亚胺及其在氮杂环合成中的应用，采用电环化-分子内Diels-Alder反应。

  DOI：

  10.1039/c39920000022

文献信息

• Periselective, Lewis acid-induced intramolecular Diels–Alder reaction of conjugated carbodiimides: efficient synthesis of nitrogen heterocycles, indolo[2,3-b]quinolines and pyrido[2,3-b]indole
  作者：Takao Saito、Hiromasa Ohmori、Takahiro Ohkubo、Shinichi Motoki

  DOI：10.1039/c39930001802

  日期：——

  A suitable Lewis acid has been found that accelerates the intramolecular Diels–Alder reaction of conjugated carbodiimides with high periselectivity control, thus providing an efficient and straightforward procedure for constructing indolo[2,3-b]quinoline and pyrido[2,3-b]indole frameworks.

  已发现一种合适的路易斯酸，它能够加速共轭碳二亚胺的分子内戴尔斯-阿尔德反应，并具有高选择性控制，从而提供一种高效且简便的方法来构建吲哚[2,3-b]喹啉和吡啶[2,3-b]吲哚框架。
• 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.

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