9-oxo-10E,12E/Z,15E/Z-octadecatrienoic acid

• 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: 9-oxo-10E,12E/Z,15E/Z-octadecatrienoic acid
• 英文别名: (10E,12E/Z,15E/Z)-9-oxooctadecatrienoic acid
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: ACHDMUPTZYZIGR-PSJRCKTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  21.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以83%的产率得到9-oxo-10E,12E/Z,15E/Z-octadecatrienoic acid
  参考文献：
  名称：

  Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols

  摘要：

  Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00087-2

文献信息

• Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols
  作者：Gilles Iacazio

  DOI：10.1016/s0009-3084(03)00087-2

  日期：2003.10

  Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides. (C) 2003 Elsevier Ireland Ltd. All rights reserved.