(15R,16S)-epoxy-α-linolenic acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (15R,16S)-epoxy-α-linolenic acid methyl ester
• 英文别名: methyl (9Z,12Z)-14-[(2R,3S)-3-ethyloxiran-2-yl]tetradeca-9,12-dienoate
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: WXOURJJDULGFAF-CZRIWUIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (9Z,12Z,15S,16S)-15-bromo-16-hydroxyoctadeca-9,12-dienoate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 20.0h， 生成 (15R,16S)-epoxy-α-linolenic acid methyl ester
  参考文献：
  名称：

  Preparation of Optically Active 15-Epoxy-a-linolenic Acids and Their Anti-Rice Blast Fungus Activities

  摘要：

  By the action of NBS in aq. DME, alpha-linolenic acid was oxidized to 15-bromo-16-hydroxy-alpha-linolenic acid in 35% conversion yield. The bromohydrin was treated with lipase-PS and vinyl acetate to give the resolved acetate and bromohydrin. (15S,16R)- and (15R,16S)-Epoxy-alpha-linolenic acids were prepared from the corresponding resolved products. A comparison of anti-rice blast fungus activities showed that an unnatural epoxide is stronger than the natural epoxide.

  DOI：

  10.3987/com-99-s147