Methyl 2-(4-methylanilino)quinoline-3-carboxylate | 138386-80-8

• 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: Methyl 2-(4-methylanilino)quinoline-3-carboxylate
• CAS: 138386-80-8
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: BPVAWLAVQUZBJY-UHFFFAOYSA-N

物化性质

• 沸点：
  435.7±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E)-3-{2-[(triphenylphosphoranylidene)amino]phenyl}-propenoic acid methyl ester 以 xylene 、 苯 为溶剂， 反应 1.0h， 生成 Methyl 2-(4-methylanilino)quinoline-3-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

• 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.
• 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
  作者：Takao Saito、Hiromasa Ohmori、Eiji Furuno、Shinichi Motoki

  DOI：10.1039/c39920000022

  日期：——

  A convenient method is described for the synthesis of conjugated carbodiimides and their application to nitrogen heterocycle synthesis via electrocyclisation–intramolecular Diels–Alder reaction.

  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。