(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1427348-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS: 1427348-99-9
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: SEMPFIRQZBGHSK-ZTRFORPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-(2-苯乙基)乙酰胺 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 四磷十氧化物 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 氘代乙腈 为溶剂， 反应 6.0h， 生成 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 、 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Molecular Structure Effects in the Asymmetric Transfer Hydrogenation of Functionalized Dihydroisoquinolines on (S,S)-[RuCl(η 6-p-cymene)TsDPEN]

  摘要：

  The asymmetric transfer hydrogenation of five dihydroisoquinolines (DHIQs) was studied by NMR spectroscopy. The DHIQs differed by substitution with methoxy groups, which had a significant effect upon the reaction performance in terms of reaction rate and enantioselectivity. The differences are most probably related to the basicity of DHIQs.

  DOI：

  10.1007/s10562-013-0996-4

文献信息

• Asymmetric transfer hydrogenation of imines catalyzed by a Noyori-type Ru(II) complex—a parametric study
  作者：Jan Pecháček、Jiří Václavík、Jan Přech、Petr Šot、Jakub Januščák、Beáta Vilhanová、Jiří Vavřík、Marek Kuzma、Petr Kačer

  DOI：10.1016/j.tetasy.2013.01.010

  日期：2013.2

  We present, to the best of our knowledge, the first parametric study of the asymmetric transfer hydrogenation of imines catalyzed by a Noyori-type catalytic complex based on ruthenium. A model imine for this study was 1-methyl-3,4-dihydroisoquinoline, and a well-known complex RuCl(eta(6)-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine) was chosen as the model catalyst. The reactions were performed in the presence of a formic acid-triethylamine mixture as the source of hydrogen.The parameters examined include general parameters, for example, concentration, temperature, and substrate-to-catalyst molar ratio, as well as parameters specific to this particular reaction, such as the amount of the hydrogenation mixture used, the ratio of its components, or the inhibitive effect of carbon dioxide. During this study, several unexpected parameters worth further investigation have emerged. (C) 2013 Elsevier Ltd. All rights reserved.