(S)-2-pentyl butanoate

• 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)-2-pentyl butanoate
• 英文别名: (S)-2-pentyl butyrate；[(2S)-pentan-2-yl] butanoate
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: DJOCFLQKCMWABC-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  2-戊醇 、 正丁酸乙烯酯 在 subtilisin Carlsberg 作用下， 生成 (S)-2-pentyl butanoate
  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

• Preparation of Passion Fruit-Typical 2-Alkyl Ester Enantiomers via Lipase-Catalyzed Kinetic Resolution
  作者：Hedwig Strohalm、Susanne Dold、Kathrin Pendzialek、Monika Weiher、Karl-Heinz Engel

  DOI：10.1021/jf100432s

  日期：2010.5.26

  fruit-typical 2-alkyl esters by capillary gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin as chiral stationary phase. An efficient method was developed to prepare the ester enantiomers via lipase-catalyzed esterifications: optically pure (R)-2-alkyl esters (ee > 99.9%) were obtained by esterification of the racemic alcohols with enantioselective Candida antarctica

  研究了通过脂肪酶催化动力学拆分制备仲醇2-戊醇，2-庚醇和2-壬醇的酯对映体（乙酸，丁酸酯，己酸酯和辛酸酯）。通过庚烷（2,3-di- O -methyl-6）的毛细管气相色谱法，对这些百香果类典型的2-烷基酯的同源系列进行了追踪，考察了市售酶制剂催化的酯化和水解反应的转化率和立体化学过程。- ø -叔丁基二）-β环糊精作为手性固定相。开发了一种通过脂肪酶催化的酯化反应制备酯对映体的有效方法：光学纯（R通过用对映选择性南极假丝酵母脂肪酶B（固定化）作为催化剂将外消旋醇酯化，可得到）-2-烷基酯（ee> 99.9％）。随后使用来自假丝酵母的脂肪酶将未反应的醇酯化，得到光学富集的（S）-酯（ee＞ 81.4％）。通过使用硅胶和氧化铝（碱性）的混合物的液体固体色谱法分离产物，得到高化学纯度和产率（＞ 40mol％）。
• Sagiroglu, Ayten; Telefoncu, Azmi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 85 - 87
  作者：Sagiroglu, Ayten、Telefoncu, Azmi

  DOI：——

  日期：——
• MOSANDL, ARMIN;DEGER, WOLFGANG, Z. LEBENSM.-UNTERSUCH. UND FORSCH., 185,(1987) N 5, 379-382
  作者：MOSANDL, ARMIN、DEGER, WOLFGANG

  DOI：——

  日期：——
• Enantioselective transesterification catalysis by nanosized serine protease subtilisin Carlsberg particles in tetrahydrofuran
  作者：Betzaida Castillo、Yamixa Delgado、Gabriel Barletta、Kai Griebenow

  DOI：10.1016/j.tet.2010.01.053

  日期：2010.3

  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