2-ethyl-3-methyl-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: 2-ethyl-3-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2S,3S)-2-ethyl-3-methyl-1,2,3,4-tetrahydroquinoline
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: ZBOCLUCAMWTOOV-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  aniline hydrochloride 、 丙醛 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 2-ethyl-3-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  One-Pot Access to 2,3-Disubstituted 1,2,3,4-Tetrahydroquinolines by Reductive Amination of Aldehydes with Sodium Cyanoborohydride

  摘要：

  Slight modification of the reductive amination Borch method (delayed addition of NaBH3CN) provided an easy one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives from enolizable aldehydes.

  DOI：

  10.3987/com-97-7999

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Benzylquinolines and 2-Functionalized and 2,3-Disubstituted Quinolines
  作者：Da-Wei Wang、Xiao-Bing Wang、Duo-Sheng Wang、Sheng-Mei Lu、Yong-Gui Zhou、Yu-Xue Li

  DOI：10.1021/jo900073z

  日期：2009.4.3

  The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines was developed by using the [Ir(COD)Cl]2/bisphosphine/I2 system with up to 96% ee. Moreover, mechanistic studies revealed the hydrogenation mechanism of quinoline involves a 1,4-hydride addition, isomerization, and 1,2-hydride addition, and the catalytic active species may be a Ir(III) complex

  通过使用[Ir（COD）Cl] 2 /双膦/ I 2体系（ee高达96％）开发了2-苄基喹啉和2-官能化和2,3-二取代喹啉的对映选择性氢化。而且，机理研究表明，喹啉的氢化机理涉及1，4-氢化物的加成，异构化和1，2-氢化物的加成，并且催化活性物质可以是与氯化物和碘化物的Ir（III）络合物。
• Silver-Catalyzed Reduction of Quinolines in Water
  作者：Yan Wang、Baobiao Dong、Zikun Wang、Xuefeng Cong、Xihe Bi

  DOI：10.1021/acs.orglett.9b01055

  日期：2019.5.17

  A ligand- and base-free silver-catalyzed reduction of quinolines and electron-deficient aromatic N-heteroarenes in water has been described. Mechanistic studies revealed that the effective reducing species was Ag–H. This versatile catalytic protocol provided facile, environmentally friendly, and practical access to a variety of 1,2,3,4-tetrahydroquinoline derivatives at room temperature.

  已经描述了在水中无配体和无碱的银催化的喹啉和电子缺乏的芳族N-杂芳烃的还原。机理研究表明，有效的还原物种是Ag–H。这种多功能的催化方案可在室温下轻松，环保且实用地接触各种1,2,3,4-四氢喹啉衍生物。
• One-Pot Access to 2,3-Disubstituted 1,2,3,4-Tetrahydroquinolines by Reductive Amination of Aldehydes with Sodium Cyanoborohydride
  作者：Guy Lewin、Corinne Schaeffer

  DOI：10.3987/com-97-7999

  日期：——

  Slight modification of the reductive amination Borch method (delayed addition of NaBH3CN) provided an easy one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives from enolizable aldehydes.