5-(3,3-dimethylbutylidene)-4-methyloxolan-2-one | 1253948-28-5

• 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: 5-(3,3-dimethylbutylidene)-4-methyloxolan-2-one
• CAS: 1253948-28-5
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: WJUSTKLSCSXZFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3,3-dimethylbutylidene)-4-methyloxolan-2-one 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3,7,7-trimethyl-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
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 5-(3,3-dimethylbutylidene)-4-methyloxolan-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