(S)-9-Acetoxy-10-fluoro-decanoic acid methyl ester | 172428-43-2

• 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: (S)-9-Acetoxy-10-fluoro-decanoic acid methyl ester
• 英文别名: methyl (9S)-9-acetyloxy-10-fluorodecanoate
• CAS: 172428-43-2
• 化学式: C₁₃H₂₃FO₄
• 分子量: 262.322
• InChiKey: OFHFOQQEVFPCBM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-9-Acetoxy-10-fluoro-decanoic acid methyl ester 在 4-二甲氨基吡啶 、 oxonium 、 三乙胺 作用下， 反应 37.0h， 生成 (S)-10-Fluoromethyl-oxecan-2-one
  参考文献：
  名称：

  Synthesis of (9R)- and (9S)-10-fluorodecan-9-olide (fluoro-phoracantholide I) first lipase-catalyzed enantioselective esterification of β-fluoroalcohols

  摘要：

  Synthesis of both enantiomers of fluoro-phoracantholide I, namely (9S)-10-fluorodecan-9-olide ((9S)-(-)-1) and (9R)-10-fluorodecan-9-olide (9R)-(+)-1, has been achieved through lipase-catalyzed enantioselective acetylation of methyl 10-fluoro-9-hydroxydecanoate (2a) with acetic anhydride in the presence of Lipase Amano PS (Pseudomonas cepacia). The higher homologue, methyl 11-fluoro-10-hydroxyundecanoate (2b) has also been resolved. These enzymatic resolutions by acetylation of omega-fluoro-(omega-1)-hydroxyalkanoic acid esters of long-chain fatty acids represent the first lipase-catalyzed enantioselective esterifications of beta-fluoroalcohols.

  DOI：

  10.1016/0957-4166(95)00375-y
• 作为产物：
  描述：

  乙酸酐 、 methyl 10-fluoro-9-hydroxydecanoate 以 甲苯 为溶剂， 反应 24.0h， 生成 (R)-10-Fluoro-9-hydroxy-decanoic acid methyl ester 、 (S)-9-Acetoxy-10-fluoro-decanoic acid methyl ester 、 (R)-9-Acetoxy-10-fluoro-decanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of (9R)- and (9S)-10-fluorodecan-9-olide (fluoro-phoracantholide I) first lipase-catalyzed enantioselective esterification of β-fluoroalcohols

  摘要：

  Synthesis of both enantiomers of fluoro-phoracantholide I, namely (9S)-10-fluorodecan-9-olide ((9S)-(-)-1) and (9R)-10-fluorodecan-9-olide (9R)-(+)-1, has been achieved through lipase-catalyzed enantioselective acetylation of methyl 10-fluoro-9-hydroxydecanoate (2a) with acetic anhydride in the presence of Lipase Amano PS (Pseudomonas cepacia). The higher homologue, methyl 11-fluoro-10-hydroxyundecanoate (2b) has also been resolved. These enzymatic resolutions by acetylation of omega-fluoro-(omega-1)-hydroxyalkanoic acid esters of long-chain fatty acids represent the first lipase-catalyzed enantioselective esterifications of beta-fluoroalcohols.

  DOI：

  10.1016/0957-4166(95)00375-y

文献信息

• Synthesis of (9R)- and (9S)-10-fluorodecan-9-olide (fluoro-phoracantholide I) first lipase-catalyzed enantioselective esterification of β-fluoroalcohols
  作者：Andreas Sattler、Günter Haufe

  DOI：10.1016/0957-4166(95)00375-y

  日期：1995.11

  Synthesis of both enantiomers of fluoro-phoracantholide I, namely (9S)-10-fluorodecan-9-olide ((9S)-(-)-1) and (9R)-10-fluorodecan-9-olide (9R)-(+)-1, has been achieved through lipase-catalyzed enantioselective acetylation of methyl 10-fluoro-9-hydroxydecanoate (2a) with acetic anhydride in the presence of Lipase Amano PS (Pseudomonas cepacia). The higher homologue, methyl 11-fluoro-10-hydroxyundecanoate (2b) has also been resolved. These enzymatic resolutions by acetylation of omega-fluoro-(omega-1)-hydroxyalkanoic acid esters of long-chain fatty acids represent the first lipase-catalyzed enantioselective esterifications of beta-fluoroalcohols.