(1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfonylphenyl]methyl]ethanamine | 1491170-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfonylphenyl]methyl]ethanamine
• CAS: 1491170-07-0
• 化学式: C₃₈H₃₆N₂O₂S
• 分子量: 584.782
• InChiKey: DNTVPSXRQOJOKA-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfinylphenyl]methyl]ethanamine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到(1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfonylphenyl]methyl]ethanamine
  参考文献：
  名称：

  Polydentate chiral heteroorganic ligands/catalysts—impact of particular functional groups on their activity in selected reactions of asymmetric synthesis

  摘要：

  The influence of each functional group in enantiomerically pure ligands 1, bearing a hydroxy moiety, a stereogenic sulfinyl group and an enantiomeric amine moiety, on ligand catalytic efficiency in enantioselective nitroaldol (Henry) reactions was investigated by subsequent transformation and/or protection of these groups. It was found that, although the absolute configuration of the amine moiety exerted a decisive influence on the stereochemical outcome of the reaction, the presence of the sulfinyl group was crucial. The hydroxy group could be replaced by a second enantiomeric amine moiety, but in order to achieve high catalytic activity of the ligand, it was necessary to retain the sulfinyl moiety in its molecule. This clearly indicated that the simultaneous presence of three coordinating centres was essential for the efficiency of the catalysts and allowed us to conclude that the original ligands 1 demonstrated a tridentate character. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.012

文献信息

• Polydentate chiral heteroorganic ligands/catalysts—impact of particular functional groups on their activity in selected reactions of asymmetric synthesis
  作者：Piotr Kiełbasiński、Michał Rachwalski、Sylwia Kaczmarczyk、Stanisław Leśniak

  DOI：10.1016/j.tetasy.2013.08.012

  日期：2013.11

  The influence of each functional group in enantiomerically pure ligands 1, bearing a hydroxy moiety, a stereogenic sulfinyl group and an enantiomeric amine moiety, on ligand catalytic efficiency in enantioselective nitroaldol (Henry) reactions was investigated by subsequent transformation and/or protection of these groups. It was found that, although the absolute configuration of the amine moiety exerted a decisive influence on the stereochemical outcome of the reaction, the presence of the sulfinyl group was crucial. The hydroxy group could be replaced by a second enantiomeric amine moiety, but in order to achieve high catalytic activity of the ligand, it was necessary to retain the sulfinyl moiety in its molecule. This clearly indicated that the simultaneous presence of three coordinating centres was essential for the efficiency of the catalysts and allowed us to conclude that the original ligands 1 demonstrated a tridentate character. (C) 2013 Elsevier Ltd. All rights reserved.