(S)-6-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline | 1364891-68-8

• 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: (S)-6-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1S)-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 1364891-68-8
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: FSCCJTKQQGRDAT-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-Menthyl chloroformate 、 (S)-6-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  The role of the aromatic ligand in the asymmetric transfer hydrogenation of the CN bond on Noyori’s chiral Ru catalysts

  摘要：

  Only four types of dimeric precursors [RuCl2(eta(6)-arene)](2) for the synthesis of Noyori's half sandwich diamine catalysts [RuCl(TsDPEN)(eta(6)-arene)] are commercially available, yet so far no study has tried to systematically evaluate how these systems perform during the asymmetric transfer hydrogenation of various 3,4-dihydroisoquinolines (i.e., the typical substrates for Noyori asymmetric transfer hydrogenation benchmarking). Experiments combined with molecular modeling allowed us to assess their properties and formulate a hypothesis clarifying the difference in enantioselectivity of these systems. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.011
• 作为产物：
  描述：

  6-甲氧基-1-甲基-3,4-二氢异喹啉 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.17h， 以92%的产率得到
  参考文献：
  名称：

  The role of the aromatic ligand in the asymmetric transfer hydrogenation of the CN bond on Noyori’s chiral Ru catalysts

  摘要：

  Only four types of dimeric precursors [RuCl2(eta(6)-arene)](2) for the synthesis of Noyori's half sandwich diamine catalysts [RuCl(TsDPEN)(eta(6)-arene)] are commercially available, yet so far no study has tried to systematically evaluate how these systems perform during the asymmetric transfer hydrogenation of various 3,4-dihydroisoquinolines (i.e., the typical substrates for Noyori asymmetric transfer hydrogenation benchmarking). Experiments combined with molecular modeling allowed us to assess their properties and formulate a hypothesis clarifying the difference in enantioselectivity of these systems. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.011

文献信息

• Enantioselective hydrogenation of cyclic imines catalysed by Noyori–Ikariya half-sandwich complexes and their analogues
  作者：B. Vilhanová、J. Václavík、P. Šot、J. Pecháček、J. Zápal、R. Pažout、J. Maixner、M. Kuzma、P. Kačer

  DOI：10.1039/c5cc06712j

  日期：——

  A method for enantioselective hydrogenation of cyclic imines with gaseous hydrogen has been developed. Easily accessible Noyori-Ikariya Ru(II) and Rh(III) complexes can be used directly without inert atmosphere. Substrate activation...

  已经开发了用气态氢对环亚胺进行对映选择性氢化的方法。易于获得的Noyori-Ikariya Ru（II）和Rh（III）配合物可在没有惰性气氛的情况下直接使用。基板活化...
• Molecular Structure Effects in the Asymmetric Transfer Hydrogenation of Functionalized Dihydroisoquinolines on (S,S)-[RuCl(η 6-p-cymene)TsDPEN]
  作者：Jiří Václavík、Jan Pecháček、Beáta Vilhanová、Petr Šot、Jakub Januščák、Václav Matoušek、Jan Přech、Simona Bártová、Marek Kuzma、Petr Kačer

  DOI：10.1007/s10562-013-0996-4

  日期：2013.6

  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.
• The role of the aromatic ligand in the asymmetric transfer hydrogenation of the CN bond on Noyori’s chiral Ru catalysts
  作者：Petr Šot、Beáta Vilhanová、Jan Pecháček、Jiří Václavík、Jakub Zápal、Marek Kuzma、Petr Kačer

  DOI：10.1016/j.tetasy.2014.08.011

  日期：2014.10

  Only four types of dimeric precursors [RuCl2(eta(6)-arene)](2) for the synthesis of Noyori's half sandwich diamine catalysts [RuCl(TsDPEN)(eta(6)-arene)] are commercially available, yet so far no study has tried to systematically evaluate how these systems perform during the asymmetric transfer hydrogenation of various 3,4-dihydroisoquinolines (i.e., the typical substrates for Noyori asymmetric transfer hydrogenation benchmarking). Experiments combined with molecular modeling allowed us to assess their properties and formulate a hypothesis clarifying the difference in enantioselectivity of these systems. (C) 2014 Elsevier Ltd. All rights reserved.