(1R,3S)-benzyl 3-((benzylamino)methyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1238366-02-3

• 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,3S)-benzyl 3-((benzylamino)methyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS: 1238366-02-3
• 化学式: C₃₃H₃₄N₂O₄
• 分子量: 522.644
• InChiKey: IGUUDDDSHZYIIW-GMCHKSTQSA-N

反应信息

• 作为反应物：
  描述：

  (1R,3S)-benzyl 3-((benzylamino)methyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以52%的产率得到N-benzyl-1-((1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanamine
  参考文献：
  名称：

  Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation

  摘要：

  The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)](2) as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.017
• 作为产物：
  描述：

  在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以0.21 g的产率得到(1R,3S)-benzyl 3-((benzylamino)methyl)-6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation

  摘要：

  The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)](2) as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.017