3,7-dimethyl-4-oxooctanoic acid | 1001185-64-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3,7-dimethyl-4-oxooctanoic acid
• 英文别名: 3,7-Dimethyl-4-oxooctanoic acid
• CAS: 1001185-64-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: NDMRRMAGZYCGRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-4-oxooctanoic acid 在 R_. glutinis AM₂₄₂ 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以43%的产率得到(4S,5R)-4-methyl-5-(3-methylbutyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Lactones 44. Microbial lactonization of γ-ketoacids

  摘要：

  Enantiomerically pure gamma-lactones ((+)-4a, (-)-5a, (+)-4b) have been obtained from the corresponding gamma-ketoacids (3a and 3b) by their biotransformations with the three fungal strains: Rhodotorula glutinis AM242, Saccharomyces cerevisiae AM464 and Chaetomium sp. KCh6670. Microbial lactonization of 3,7-dimethyl-4-oxooctanoic acid (3a) with R. glutinis AM242 afforded the (+)-(4S,5R)-trans-gamma-lactone (4a) with 99% ee, while Chaetomium sp. KCh6670 proved to be the best biocatalyst for the bioreduction and following lactonization of gamma-ketoacid (3a), which afforded (-)-cis-gamma-lactone (5a) with 99% ee. Biotransformation of 3,7,7-trimethyl-4-oxooctanoid acid (3b) in the culture of S. cerevisiae AM464 gave the corresponding (+)-trans-gamma-lactone (4b) with 99% ee. The odours of the racemic gamma-lactones ((+/-)-4a, (+/-)-5a, (+/-)-4b and (+/-)-5b) and optically pure isomers ((+)-4a, (-)-5a, (+)-4b) were evaluated. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.04.014
• 作为产物：
  描述：

  4-Methyl-5-(3-methylbutyliden)-4,5-dihydrofuran-2(3H)-on 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3,7-dimethyl-4-oxooctanoic acid
  参考文献：
  名称：

  Lactones 44. Microbial lactonization of γ-ketoacids

  摘要：

  Enantiomerically pure gamma-lactones ((+)-4a, (-)-5a, (+)-4b) have been obtained from the corresponding gamma-ketoacids (3a and 3b) by their biotransformations with the three fungal strains: Rhodotorula glutinis AM242, Saccharomyces cerevisiae AM464 and Chaetomium sp. KCh6670. Microbial lactonization of 3,7-dimethyl-4-oxooctanoic acid (3a) with R. glutinis AM242 afforded the (+)-(4S,5R)-trans-gamma-lactone (4a) with 99% ee, while Chaetomium sp. KCh6670 proved to be the best biocatalyst for the bioreduction and following lactonization of gamma-ketoacid (3a), which afforded (-)-cis-gamma-lactone (5a) with 99% ee. Biotransformation of 3,7,7-trimethyl-4-oxooctanoid acid (3b) in the culture of S. cerevisiae AM464 gave the corresponding (+)-trans-gamma-lactone (4b) with 99% ee. The odours of the racemic gamma-lactones ((+/-)-4a, (+/-)-5a, (+/-)-4b and (+/-)-5b) and optically pure isomers ((+)-4a, (-)-5a, (+)-4b) were evaluated. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.04.014

文献信息

• Lactones 44. Microbial lactonization of γ-ketoacids
  作者：Agnieszka Leśniak、Małgorzata Smuga、Agata Białońska、Józef Kula、Czesław Wawrzeńczyk

  DOI：10.1016/j.molcatb.2014.04.014

  日期：2014.8

  Enantiomerically pure gamma-lactones ((+)-4a, (-)-5a, (+)-4b) have been obtained from the corresponding gamma-ketoacids (3a and 3b) by their biotransformations with the three fungal strains: Rhodotorula glutinis AM242, Saccharomyces cerevisiae AM464 and Chaetomium sp. KCh6670. Microbial lactonization of 3,7-dimethyl-4-oxooctanoic acid (3a) with R. glutinis AM242 afforded the (+)-(4S,5R)-trans-gamma-lactone (4a) with 99% ee, while Chaetomium sp. KCh6670 proved to be the best biocatalyst for the bioreduction and following lactonization of gamma-ketoacid (3a), which afforded (-)-cis-gamma-lactone (5a) with 99% ee. Biotransformation of 3,7,7-trimethyl-4-oxooctanoid acid (3b) in the culture of S. cerevisiae AM464 gave the corresponding (+)-trans-gamma-lactone (4b) with 99% ee. The odours of the racemic gamma-lactones ((+/-)-4a, (+/-)-5a, (+/-)-4b and (+/-)-5b) and optically pure isomers ((+)-4a, (-)-5a, (+)-4b) were evaluated. (C) 2014 Elsevier B.V. All rights reserved.