4-Hydroxy-undecanoic acid propyl ester | 139126-66-2

• 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: 4-Hydroxy-undecanoic acid propyl ester
• 英文别名: Propyl 4-hydroxyundecanoate
• CAS: 139126-66-2
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: DZLZDOIBUJVXJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-undecanoic acid propyl ester 生成 Undecanoic acid, 4-hydroxy-, propyl ester, (R)-
  参考文献：
  名称：

  Lipase-catalyzed transesterification in organic solvents: Preparation and enantiodifferentiation of optically enriched 4(5)-alkylated 1,4(1,5)-olides

  摘要：

  Porcine pancreatic lipase (PPL) catalyzed intramolecular transesterification of n-propyl esters of 4(5)-hydroxyalkanoic acids (C5-C12) in diethyl ether (20-degrees-C) yielded (S)-4-alkylated 1,4-olides of high optical purity (ee > 80%) and optically pure (R)-4-hydroxyalkanoic-n-propylesters, but exhibited low enantioselectivity for (S)-5-alkylated 1,5-olides (ee = 10-20%). The chiral analysis of 4(5)-hydroxyalkanoic esters was performed by HRGC and HPLC after their derivatization with (R)-(+)-1-phenylethylisocyanate, (S)-O-acetyllactic acid chloride, and (R)-(+)-alpha-methoxy-alpha-trifluoromethylphenylacetic acid chloride. The enantiodifferentiation of 1,4(1,5)-olides was achieved by HPLC on a chiral phase (ChiraSpher) using an on-line optical rotation detector (ChiraMonitor).

  DOI：

  10.1016/s0957-4166(00)82013-3