6-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline | 1094741-58-8

• 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: 6-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-[(2R)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl]ethanone
• CAS: 1094741-58-8
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: LUFRUTIWVVDXIW-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-甲基喹啉-6-基)乙酮 在 Ru(OTf)(TsDPEN)(η6-p-cymene) 、 氢气 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 25.0 ℃ 、5.07 MPa 条件下， 反应 24.0h， 以87%的产率得到6-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  使用可回收的不含膦的手性阳离子钌催化剂对喹啉进行加氢：提高催化剂稳定性和在离子液体中的选择性。

  摘要：

  DOI：

  10.1002/anie.200802237

文献信息

• Hydrogenation of Quinolines Using a Recyclable Phosphine-Free Chiral Cationic Ruthenium Catalyst: Enhancement of Catalyst Stability and Selectivity in an Ionic Liquid
  作者：Haifeng Zhou、Zhiwei Li、Zhijian Wang、Tianli Wang、Lijin Xu、Yanmei He、Qing-Hua Fan、Jie Pan、Lianquan Gu、Albert S. C. Chan

  DOI：10.1002/anie.200802237

  日期：2008.10.20
• Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium‐Catalyzed Asymmetric Hydrogenation in Ionic Liquid
  作者：Zi‐Yuan Ding、Tianli Wang、Yan‐Mei He、Fei Chen、Hai‐Feng Zhou、Qing‐Hua Fan、Qingxiang Guo、Albert S. C. Chan

  DOI：10.1002/adsc.201300698

  日期：2013.12.16

  AbstractAsymmetric hydrogenation reactions of quinolines and 3,4‐dihydroisoquinolines using the chiral cationic ruthenium complex Ru(TsDPEN) [TsDPEN=N‐(p‐toluenesulfonyl)‐1,2‐diphenylethylenediamine] as catalyst in neat imidazolium ionic liquids have been investigated. The catalytic performance was influenced by the anion of the ionic liquids for both substrate classes. A range of 2‐alkyl‐substituted 1,2,3,4‐tetrahydroquinolines and 1‐alkyl‐substituted 1,2,3,4‐tetrahydroisoquinolines was obtained in high yields with up to >99% ee. Interestingly, the hydrogenation of quinoline derivatives bearing a carbonyl group was selective for the CN (quinoline) over the CO (ketone) bonds, while such a unique chemoselectivity was not observed in methanol. Furthermore, the ruthenium catalysts could be easily recycled at least 5 times in the asymmetric hydrogenation of 3,4‐dihydroisoquinoline by solvent extraction. To further facilitate the recovery of catalyst and reduce the use of organic solvent, a thin film of ionic liquid containing Ru(TsDPEN) was supported on silica gels. This supported ionic liquid‐phase catalyst was effective in the asymmetric hydrogenation of quinoline, and could be recycled at least 6 times by simple filtration.magnified image