(+/-)-trans-4-ethoxy-2,6-dimethyl-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: (+/-)-trans-4-ethoxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2R,4R)-4-ethoxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: HGKYVZNOMXOEKP-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 、 乙烯基乙醚 以 various solvent(s) 为溶剂， 反应 3.0h， 生成 (+/-)-trans-4-ethoxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline 、 (+/-)-cis-4-ethoxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Uncatalysed Domino Reaction in Hexafluoroisopropanol: A Simple Protocol for the Synthesis of Tetrahydroquinoline Derivatives

  摘要：

  在六氟丙醇中，从苯胺和烯醇醚出发，在没有路易斯酸催化的情况下，通过多米诺反应合成了多种四氢喹啉，且收率很高。该溶剂被证明可促进苯胺与烯醇醚的亲核加成反应以及氮杂-迪尔斯-阿尔德反应。

  DOI：

  10.1055/s-2003-41074

文献信息

• Uncatalysed Domino Reaction in Hexafluoroisopropanol: A Simple Protocol for the Synthesis of Tetrahydroquinoline Derivatives
  作者：Danièle Bonnet-Delpon、Andrea Di Salvo、Maria Vittoria Spanedda、Michèle Ourévitch、Benoit Crousse

  DOI：10.1055/s-2003-41074

  日期：——

  A range of tetrahydroquinolines were synthesised in excellent yields through a domino reaction performed in hexafluoropropanol, starting from anilines and enol ethers and in the absence of Lewis acid catalysis. This solvent was shown to promote the nucleophilic addition of anilines to enol ethers as well as the aza-Diels-Alder reaction.

  在六氟丙醇中，从苯胺和烯醇醚出发，在没有路易斯酸催化的情况下，通过多米诺反应合成了多种四氢喹啉，且收率很高。该溶剂被证明可促进苯胺与烯醇醚的亲核加成反应以及氮杂-迪尔斯-阿尔德反应。
• CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization
  作者：Vellaisamy Sridharan、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1016/j.tet.2006.11.002

  日期：2007.1

  The CAN-catalyzed reaction between anilines and vinyl ethers at room temperature provides a convenient and efficient access to 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines. This reaction is stereoselective, favouring a cis arrangements for the alkoxy and methyl groups, and involves a three-component process that leaves a molecule of alcohol as the only side product. 2-Methylquinoline derivatives were efficiently prepared from 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines by Pd-C-promoted dehydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.