6-chloro-N-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine

• 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: 6-chloro-N-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine
• 英文别名: 6-chloro-4-(4-chloroanilino)-2-methyl-1,2,3,4-tetrahydroquinoline；(2S,4S)-6-chloro-N-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine
• 化学式: C₁₆H₁₆Cl₂N₂
• 分子量: 307.222
• InChiKey: FGUNEERUJNTBKF-QFYYESIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基己内酰胺 、 对氯苯胺 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-chloro-N-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine 、 (±)-cis-(6-chloro-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-(4-chloro-phenyl)-amine
  参考文献：
  名称：

  自由基阳离子盐诱导苯胺和N-乙烯基酰胺之间的串联环化：2-甲基-4-苯胺基1,2,3,4-四氢喹啉衍生物的合成

  摘要：

  研究了由TBPA +诱导的亚胺与N-乙烯基内酰胺的串联环化反应，并基于其中N-乙烯基内酰胺起作用的多米诺过程，合成了一系列2-甲基-4-苯胺基-1,2,3,4-四氢喹啉作为乙醛的替代物。提出了单一的电子转移机制，自由基阳离子盐既充当路易斯酸又充当一种电子氧化剂来诱导这种转变。

  DOI：

  10.1016/j.tetlet.2010.10.106

文献信息

• Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao-dong Jia、Yan Ren、Cong-de Huo、Wen-Juan Wang、Xiang-Ning Chen、Xiao-Lan Xu、Xi-cun Wang

  DOI：10.1016/j.tetlet.2010.10.106

  日期：2010.12

  A tandem cyclization of imines with N-vinyllactams induced by TBPA+ was investigated, and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde surrogate. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation

  研究了由TBPA +诱导的亚胺与N-乙烯基内酰胺的串联环化反应，并基于其中N-乙烯基内酰胺起作用的多米诺过程，合成了一系列2-甲基-4-苯胺基-1,2,3,4-四氢喹啉作为乙醛的替代物。提出了单一的电子转移机制，自由基阳离子盐既充当路易斯酸又充当一种电子氧化剂来诱导这种转变。
• Radical cation salts induced domino reaction of anilines with enol ethers: Synthesis of 1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao Dong Jia、Yan Ren、Cong Dde Huo、Wen Juan Wang、Xiang Ning Chen、Qiong Fu、Xi Cun Wang

  DOI：10.1016/j.cclet.2010.12.038

  日期：2011.6

  A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA+ (5 mol%) was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized. Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction, they serve as surrogates of acetaldehyde, producing a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines

  研究了催化量的TBPA +（5 mol％）诱导的苯胺与环状和无环烯醇醚的多米诺反应，并合成了一系列的2,4-二取代-1,2,3,4-四氢喹啉。与环状烯醇醚不同，当在反应中使用无环烯醇醚时，它们充当乙醛的替代物，产生一系列2-甲基-4-苯胺基1,2,3,4-四氢喹啉。提出了单一电子转移机制以合理化产物的形成。
• Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide salt and its application as a recyclable catalyst for the synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines
  作者：Boddula Rajender、Srinivasan Palaniappan

  DOI：10.1016/j.catcom.2014.08.011

  日期：2014.12

  Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide is successfully carried out using bromodimethylsulfonium bromide. Poly(2-bromoaniline)-bromide salt was obtained in a dry amorphous nature, having high conductivity (2.5 S/cm) with agglomerated spherical morphology. Poly(2-bromoaniline)bromide salt was proved to be a novel, efficient, reusable, cheaper and eco-friendly polymer-based solid acid catalyst in the reaction between aromatic amines and N-vinyl lactam under solvent-free conditions to provide 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines. These 2,4-disubstituted tetrahydroquinolines were synthesized with trans selectivity. (C) 2014 Elsevier B.V. All rights reserved.