(R)-3-hydroxyoctanenitrile | 183232-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-hydroxyoctanenitrile
• 英文别名: (3R)-3-hydroxyoctanenitrile
• CAS: 183232-07-7
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: CNXAYZCPQRIELB-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxyoctanenitrile 、 苯甲酰氯 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals

  摘要：

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

  DOI：

  10.1021/jo1013788
• 作为产物：
  描述：

  (R)-5-pentyl-2-isoxazoline 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以88%的产率得到(R)-3-hydroxyoctanenitrile
  参考文献：
  名称：

  Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals

  摘要：

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

  DOI：

  10.1021/jo1013788

文献信息

• Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals
  作者：Antti Pohjakallio、Petri M. Pihko、Jun Liu

  DOI：10.1021/jo1013788

  日期：2010.10.1

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.