(1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfinylphenyl]methyl]ethanamine | 1443212-53-0

• 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]sulfinylphenyl]methyl]ethanamine
• CAS: 1443212-53-0
• 化学式: C₃₈H₃₆N₂OS
• 分子量: 568.783
• InChiKey: OALCCPWYUTZWHJ-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  42
• 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：
  60.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfinylphenyl]methyl]ethanamine 在 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以69%的产率得到(1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfanylphenyl]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
• 作为产物：
  描述：

  (2-{[2-(羟基甲基)苯基]硫代}苯基)甲醇 在 三乙酰氧基硼氢化钠 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfinylphenyl]methyl]ethanamine
  参考文献：
  名称：

  Efficient catalysts for asymmetric Mannich reactions

  摘要：

  针对酮、醛和胺（对甲氧基苯胺）的直接不对称三组分曼尼希反应开发了高效手性催化剂。获得了相应的 β-氨基羰基化合物（曼尼希加合物），化学收率高，对映和非对映选择性极佳。通过使用超声波对反应条件进行了优化，并评估了催化剂的某些结构分子对曼尼希产物的化学收率和立体选择性的影响。

  DOI：

  10.1039/c3ob40681d
• 作为试剂：
  描述：

  硝基甲烷 、 邻甲氧基苯甲醛 在 (1R)-1-naphthalen-1-yl-N-[[2-[2-[[[(1R)-1-naphthalen-1-ylethyl]amino]methyl]phenyl]sulfinylphenyl]methyl]ethanamine 、 copper(II) acetate monohydrate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以92%的产率得到(1R)-1-(2-甲氧基苯基)-2-硝基乙醇
  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.
• Efficient catalysts for asymmetric Mannich reactions
  作者：Michał Rachwalski、Tim Leenders、Sylwia Kaczmarczyk、Piotr Kiełbasiński、Stanisław Leśniak、Floris P. J. T. Rutjes

  DOI：10.1039/c3ob40681d

  日期：——

  Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.

  针对酮、醛和胺（对甲氧基苯胺）的直接不对称三组分曼尼希反应开发了高效手性催化剂。获得了相应的 β-氨基羰基化合物（曼尼希加合物），化学收率高，对映和非对映选择性极佳。通过使用超声波对反应条件进行了优化，并评估了催化剂的某些结构分子对曼尼希产物的化学收率和立体选择性的影响。