methyl (S)-10-((R)-2-acetoxy-2-phenylacetoxy)octadecanoate | 146064-84-8

• 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: methyl (S)-10-((R)-2-acetoxy-2-phenylacetoxy)octadecanoate
• CAS: 146064-84-8
• 化学式: C₂₉H₄₆O₆
• 分子量: 490.681
• InChiKey: XHJOOKNOPMAYOP-XTEPFMGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  35.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  10-羟基硬脂酸甲酯 在 重氮甲烷 、 lipases CALB 作用下， 以 aq. phosphate buffer 、 乙醚 、 丙酮 为溶剂， 反应 60.0h， 生成 methyl (S)-10-((R)-2-acetoxy-2-phenylacetoxy)octadecanoate
  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