4-Benzyl-1-ethyl-1,2,3,4-tetrahydroquinoline

• 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: 4-Benzyl-1-ethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 4-benzyl-1-ethyl-3,4-dihydro-2H-quinoline
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: DLSOQHNWZQROTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 N-乙基苯胺 、 乙烯基乙醚 、 alkaline earth salt of/the/ methylsulfuric acid 生成 4-Benzyl-1-ethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with .alpha.,.beta.-Unsaturated Ethers. A Novel Route to 1,4- and 1,3-Disubstituted 1,2,3,4-Tetrahydroquinolines

  摘要：

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 3, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo acid-catalyzed reactions with ethyl vinyl ether to give 1-allkyl-4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 10 and their benzotriazol-2-yl isomers 11. The reaction mechanism involves formation of 1-alkyl-4-ethoxy-1,2,3,4-tetrahydroquinolines 8 as isolable intermediates, followed by substitution of the ethoxy group in 8 with benzotriazole to produce 10 and 11, Treatment with Grignard reagents in toluene converts compounds 10 and 11 in good yield to 4-alkyl- or 4-aryltetrahydroquinolines 12. 2,3-Dihydrofuran and 3,4-dihydro-2H-pyran undergo similar reaction sequences giving tetrahydroquinolines additionally substituted by 3-(beta-hydroxyethyl) and 3-(gamma-hydroxypropyl) groups, respectively. The stereochemistry of 1,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines is assigned on the basis of NOE methodology. An unusual reduction of the benzotriazolyl moiety to a phenylamino group is observed in the case of product 43 obtained from the reaction of 10-(benzotriazol-1-ylmethyl)-4H-phenothiazine with ethyl vinyl ether.

  DOI：

  10.1021/jo00113a043