R-(-)-2-methyl-5,6,7,8-tetrahydroquinolin-8-amine (R,R)-(+)-L-tartrate | 1621392-97-9

• 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: R-(-)-2-methyl-5,6,7,8-tetrahydroquinolin-8-amine (R,R)-(+)-L-tartrate
• CAS: 1621392-97-9
• 化学式: C₄H₆O₆*C₁₀H₁₄N₂
• 分子量: 312.323
• InChiKey: UWCFEBMASPUQMQ-KZKMUFAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153.97
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  L-酒石酸 、 2-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine 以 乙醇 为溶剂， 以58%的产率得到R-(-)-2-methyl-5,6,7,8-tetrahydroquinolin-8-amine (R,R)-(+)-L-tartrate
  参考文献：
  名称：

  8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH)

  摘要：

  Aqua iridium(III) complexes with 8-amino-5,6,7,8-tetrahydroquinolines CAMPY L1 and its derivatives as chiral ligands proved to be very efficient catalysts for the reduction of a wide range of prochiral aryl ketones, revealing a variety of behaviours in terms of reaction rate and stereoselectivity. As standard substrates, differently substituted acetophenones were studied and good enantioselectivity (86% ee) was achieved in the reduction of 1-(o-tolyl)ethan-1-one 6. Particularly interesting was the ATH reaction in the case of beta-amino keto esters, precursors of beta-lactams and azetidinones. The best results were obtained with [Cp*Ir(H2O)(L1)]SO4 affording the corresponding diastereomeric alcohols in an (R,S)-configuration with an excellent 99% ee in the reduction of 2-(benzamido methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl) propanoate 12. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.06.003