(R)-10-Fluoro-9-hydroxy-decanoic acid methyl ester | 172586-02-6

• 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: (R)-10-Fluoro-9-hydroxy-decanoic acid methyl ester
• 英文别名: methyl (9R)-10-fluoro-9-hydroxydecanoate
• CAS: 172586-02-6
• 化学式: C₁₁H₂₁FO₃
• 分子量: 220.284
• InChiKey: HMZFXWJWKXBUNI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-10-Fluoro-9-hydroxy-decanoic acid methyl ester 在 oxonium 作用下， 以79%的产率得到(R)-10-Fluoro-9-hydroxy-decanoic acid
  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：

  methyl 10-fluoro-9-hydroxydecanoate 生成 (R)-10-Fluoro-9-hydroxy-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.