9-D-Acetoxy-octadecansaeure | 23559-92-4

• 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-D-Acetoxy-octadecansaeure
• CAS: 23559-92-4
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: JEPMPLIABMSOKK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  24.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-D-Acetoxy-octadecansaeure 在 potassium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (R)-9-hydroxystearic acid
  参考文献：
  名称：

  Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation

  摘要：

  Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas' rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.017
• 作为产物：
  描述：

  乙酸酐 、 methyl 9-(acetoxy)octadecanoate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 9-D-Acetoxy-octadecansaeure
  参考文献：
  名称：

  Absolute configurations of 13-hydroxydocosanoic and 17-hydroxyoctadecanoic acids

  摘要：

  13-D-和13-L-羟基二十二酸甲酯已从9-D-和9-L-羟基十八烷酸合成。将这些酯与由波尔多曲霉产生的13-羟基二十二酸甲酯进行比较，结果显示天然产物具有L-构型。已从由顶芽酵母产生的17-羟基十八烷酸制备了已知的2-D-辛醇，表明该酸也具有L-构型。然而，大多数天然存在的长链羟基酸具有D-构型。

  DOI：

  10.1139/v68-616