(R)-ε-decalactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-ε-decalactone
• 英文别名: (7R)-7-butyloxepan-2-one
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: YKVIWISPFDZYOW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methyl-6-hydroxydecanamide 在 Pseudomonas cepacia lipase 、 sodium hydroxide 作用下， 以 甲醇 、 正己烷 、 环戊基甲醚 为溶剂， 反应 43.0h， 生成 (R)-ε-decalactone
  参考文献：
  名称：

  Enantioselective Synthesis of ε-Lactones by Lipase-Catalyzed Resolution

  摘要：

  Synthesis of optically active e-dodecalactone (1) by lipase-catalyzed enantioselective acylation with racemic N-alkyl-6-hydroxydodecanamide (rac-2) as a substrate was attempted. Lipase PS-catalyzed acetylation using rac-2 progressed efficiently, and both enantiomers of 1 were obtained with over 90% optical purities.

  DOI：

  10.3987/com-12-12426

文献信息

• Pchelka, Beata K.; Gelo-Pujic, Mirjana; Guibe-Jampel, Eryka, Journal of the Chemical Society. Perkin transactions I, 1998, # 17, p. 2625 - 2627
  作者：Pchelka, Beata K.、Gelo-Pujic, Mirjana、Guibe-Jampel, Eryka

  DOI：——

  日期：——
• Resolution of racemic ε-lactones
  作者：R. Fellous、L. Lizzani-Cuvelier、M.A. Loiseau、E. Sassy

  DOI：10.1016/s0957-4166(00)86202-3

  日期：1994.3

  Kinetic resolution of racemic epsilon-lactones by Pig Liver Esterase give optically active R (+) epsilon-lactones. When alkyl group is higher than propyl, Horse Liver Esterase leads to the destruction of the opposite enantiomer. Enantiomeric excess is easily evaluated by G.C. on a chiral stationary phase.
• Comparison of microbiologically and enzymatically mediated Baeyer–Villiger oxidations: synthesis of optically active caprolactones
  作者：Véronique Alphand、Roland Furstoss、Sandrine Pedragosa-Moreau、Stanley M. Roberts、Andrew J. Willetts

  DOI：10.1039/p19960001867

  日期：——

  Optically active a-substituted caprolactones (7-substituted oxepan-2-ones) were obtained by biocatalysed Baeyer-Villiger oxidations of various a-substituted cyclohexanones using either whole-cells of Acinetobacter TD63 or a purified cyclohexanone monooxygenase from Ps. putida NCIMB 10007(MO2). A refinement of the previously established active site model is proposed.
• Enantioselective Synthesis of ε-Lactones by Lipase-Catalyzed Resolution
  作者：Yasutaka Shimotori、Masakazu Aoyama、Hidetaka Tsukasa、Tetsuo Miyakoshi

  DOI：10.3987/com-12-12426

  日期：——

  Synthesis of optically active e-dodecalactone (1) by lipase-catalyzed enantioselective acylation with racemic N-alkyl-6-hydroxydodecanamide (rac-2) as a substrate was attempted. Lipase PS-catalyzed acetylation using rac-2 progressed efficiently, and both enantiomers of 1 were obtained with over 90% optical purities.