(-)-2-exo-ethylamino-7-syn-hydroxy-norbornane | 911054-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-2-exo-ethylamino-7-syn-hydroxy-norbornane
• 英文别名: (1S,2R,4R,7S)-2-(ethylamino)bicyclo[2.2.1]heptan-7-ol
• CAS: 911054-35-8
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: DNKYCPNOLQOQJP-XAVMHZPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-2-exo-ethylamino-7-syn-hydroxy-norbornane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (-)-2-exo-N,N-diethylamino-7-syn-hydroxy-norbornane
  参考文献：
  名称：

  Synthesis of chiral norbornane derivatives as γ-amino alcohol catalysts: the effect of the functional group positions on the chirality transfer

  摘要：

  Starting from (1S,4R) chiral ketone (+)-6, we developed a synthetic route to the synthesis of new chiral gamma-amino alcohols (+)- and (-)-syn-2-amino-7-hydroxy norbornane derivatives with excellent yields and enantiomeric excesses (up to 99%). These compounds were tested as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde presenting moderate results. The results obtained, compared with others previously reported, showed that the relative disposition of the amino and hydroxyl groups on C(2) and C(7) positions, play an important role in the catalytic activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.029
• 作为产物：
  描述：

  (-)-2-exo-amino-7-syn-hydroxy-norbornane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (-)-2-exo-ethylamino-7-syn-hydroxy-norbornane
  参考文献：
  名称：

  Synthesis of chiral norbornane derivatives as γ-amino alcohol catalysts: the effect of the functional group positions on the chirality transfer

  摘要：

  Starting from (1S,4R) chiral ketone (+)-6, we developed a synthetic route to the synthesis of new chiral gamma-amino alcohols (+)- and (-)-syn-2-amino-7-hydroxy norbornane derivatives with excellent yields and enantiomeric excesses (up to 99%). These compounds were tested as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde presenting moderate results. The results obtained, compared with others previously reported, showed that the relative disposition of the amino and hydroxyl groups on C(2) and C(7) positions, play an important role in the catalytic activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.029