(+)(S)-sec-butyl butyrate | 116836-55-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)(S)-sec-butyl butyrate
• 英文别名: (+)(S)-sek.-Butylbutyrat；(S)-butanoic acid, 1-methylpropyl ester；(+)-2-Butyl butyrate；[(2S)-butan-2-yl] butanoate
• CAS: 116836-55-6
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: QJHDFBAAFGELLO-ZETCQYMHSA-N

物化性质

• 沸点：
  152.5±0.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  正丁酸乙烯酯 、 仲丁醇 在 subtilisin Carlsberg 作用下， 生成 (+)(S)-sec-butyl butyrate
  参考文献：
  名称：

  Enantioselective transesterification catalysis by nanosized serine protease subtilisin Carlsberg particles in tetrahydrofuran

  摘要：

  Enzyme catalysis in organic solvents is a powerful tool for stereo-selective synthesis but the enantioselectivity is still hard to pi edict To overcome this obstacle. we employed a nanoparticulate formulation of subtilisin Carlsberg (SC) and designed a series of 14 structurally related racemic alcohols They were employed in the model transesterification reaction with vinyl butyrate and the enantioselectivities were determined. In general. short alcohol side chains led to low enantioselectivties, while larger and bulky side chains caused better discrimination of the enantiomers by the enzyme With several bulky substrates high enantioselectivities with E>100 were obtained Computational modeling highlighted that key to high enantioselectivity is the discrimination of the R and S substrates by the sole hydrophobic binding pocket based on their size and bulkiness While bulky S enantiomer side chains could be accommodated within the binding pocket, bulky R enantiomer side chains could not However, when also the S enantiomer side chain becomes too large and does not fit into the binding pocket anymore. enantioselectivity accordingly drops (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.053

文献信息

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