(1S,2R)-1-aminomethyl-3,3-dimethylnorbornan-2-ol | 773832-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R)-1-aminomethyl-3,3-dimethylnorbornan-2-ol
• 英文别名: (1S,2R,4R)-1-(aminomethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 773832-32-9
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: HQNXREZGKYCHPT-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-aminomethyl-3,3-dimethylnorbornan-2-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (1S,2R)-1-[(ethylamino)methyl]-3,3-dimethylnorbornan-2-ol
  参考文献：
  名称：

  The role of conformational flexibility on the catalytic activity of norbornane-derived β-, γ- and δ-amino alcohols

  摘要：

  Enantiopure norbornane-based gamma-amino alcohols 1-4 have been obtained from (+)-camphor and their catalytic behaviour as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde compared to these described for homologous beta- and delta-amino alcohols. This has allowed the first study on the influence of the size of the catalytic zinc-chelate ring on the catalytic activity, which results in the unexpected observance of a non-linear correlation between enantioselectivity and chelate ring size (conformational flexibility). An empirical rationalisation of the observed phenomenon was realised on the basis of consideration of the energetically-favoured Noyori-type transition states. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.03.007
• 作为产物：
  描述：

  (+)-(1S)-3,3-dimethyl-2-oxo-1-norbornanecarbonitrile 在 lithium aluminium tetrahydride 作用下， 反应 6.0h， 以79%的产率得到(1S,2R)-1-aminomethyl-3,3-dimethylnorbornan-2-ol
  参考文献：
  名称：

  Synthesis of enantiopure norbornane derivatives. Effect of bridgehead substituent on the π-facial selectivity of the reduction of 2-norbornanones and their oximes

  摘要：

  DOI：

  10.1016/s0957-4166(98)00132-3