[(1S)-2-oxocyclopentyl]methyl acetate | 168416-75-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(1S)-2-oxocyclopentyl]methyl acetate
• CAS: 168416-75-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: OACYHGIVQXLNCM-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙二醇 、 [(1S)-2-oxocyclopentyl]methyl acetate 在 4-甲基苯磺酸吡啶 作用下， 以72%的产率得到Acetic acid (S)-1-(1,4-dioxa-spiro[4.4]non-6-yl)methyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Curcumanolide A Using Enzymatic Transesterification of meso-Spirodiol

  摘要：

  meso-Spirodiol 12 and spirodiacetate 13 were stereoselectively prepared using pi-face selective Grignard addition to norbornanone 7. Asymmetric transesterification of meso-diol and hydrolysis of meso-diacetate were studied using lipases. Pseudomonas fluorescens lipase-catalyzed transesterification of meso-diol 12 afforded the monoacetate (-)-21 of high enantiomeric excess (>99% ee). The formal synthesis of(-)-curcumanolide A has been achieved from the optically active (-)-21.

  DOI：

  10.1021/jo962150r
• 作为产物：
  描述：

  2-(acetoxymethyl)cyclopentanol 在 pyridinium chlorochromate 作用下， 以60%的产率得到[(1S)-2-oxocyclopentyl]methyl acetate
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Curcumanolide A Using Enzymatic Transesterification of meso-Spirodiol

  摘要：

  meso-Spirodiol 12 and spirodiacetate 13 were stereoselectively prepared using pi-face selective Grignard addition to norbornanone 7. Asymmetric transesterification of meso-diol and hydrolysis of meso-diacetate were studied using lipases. Pseudomonas fluorescens lipase-catalyzed transesterification of meso-diol 12 afforded the monoacetate (-)-21 of high enantiomeric excess (>99% ee). The formal synthesis of(-)-curcumanolide A has been achieved from the optically active (-)-21.

  DOI：

  10.1021/jo962150r

文献信息

• Application of enzymic Baeyer–Villiger oxidations of 2-substituted cycloalkanones to the total synthesis of (R)-(+)-lipoic acid
  作者：Brian Adger、M. Teresa Bes、Gideon Grogan、Ray McCague、Sandrine Pedragosa-Moreau、Stanley M. Roberts、Raffaella Villa、Peter W. H. Wan、Andew J. Willetts

  DOI：10.1039/c39950001563

  日期：——

  Oxidation of ketones 1a–h using a monooxygenase from Pseudomonas putida NCIMB 10007 gave the lactones 2a–h in optically active form: lactone 2h was converted into (R)-(+)-lipoic acid 9.

  使用来自假单胞菌Pseudomonas putida NCIMB 10007的单氧化酶对酮类化合物1a–h进行氧化，得到了光学活性的内酯2a–h：内酯2h被转化为(R)-(+)-α-硫辛酸9。