(R)-N-methyl-N-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide | 1621392-98-0

• 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)-N-methyl-N-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide
• 英文别名: N-methyl-N-[(8R)-5,6,7,8-tetrahydroquinolin-8-yl]acetamide
• CAS: 1621392-98-0
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: TXVPFLONXUKCGQ-LLVKDONJSA-N

物化性质

• 沸点：
  369.8±21.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 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：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-methyl-N-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide 在 盐酸 、 水 作用下， 以100 mg的产率得到(R)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine
  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
• 作为产物：
  描述：

  N-[(8R)-5,6,7,8-四氢-8-喹啉基]-乙酰胺 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-N-methyl-N-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide
  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