(1R,3S)-3-Hydroxy-cyclopentanecarboxylic acid butyl ester | 174292-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S)-3-Hydroxy-cyclopentanecarboxylic acid butyl ester
• 英文别名: Cyclopentanecarboxylic acid, 3-hydroxy-, butyl ester, (1R-cis)-；butyl (1R,3S)-3-hydroxycyclopentane-1-carboxylate
• CAS: 174292-60-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: PIQNTMWYJNKKBL-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-Oxo-cyclopentanecarboxylic acid butyl ester 在 sodium dithionite 作用下， 生成 (1R,3S)-3-Hydroxy-cyclopentanecarboxylic acid butyl ester 、 (1S,3R)-3-Hydroxy-cyclopentanecarboxylic acid butyl ester 、 (1S,3S)-3-Hydroxy-cyclopentanecarboxylic acid butyl ester
  参考文献：
  名称：

  Horse liver alcohol dehydrogenase-catalyzed enantioselective reduction of cyclic ketones: The effect of the hydrophobic side chain of the substrate on the stereoselectivity of the reaction

  摘要：

  Horse liver alcohol dehydrogenase (HLADH)-catalyzed enantioselective reductions of alkyl3-oxocyclopentanecarboxylates, endo-5-acyloxybicyclo[2.2.1]heptan-2-ones and exo-5-acyloxybicyclo[2.2.1]heptan-2-ones gave the corresponding homochiral alcohols and ketones and the interaction between the hydrophobic side chain of the substrate and the hydrophobic zone in the active site played an important role in the specificity of the reduction. The stereoselectivities of the reactions were interpreted on the basis of the cubic space section model and a new rule, which contributes to development of a specificity analysis on the basis of the model, is introduced.

  DOI：

  10.1016/0957-4166(95)00396-7