(S)-4-phenyl-2-butyl butyrate

• 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)-4-phenyl-2-butyl butyrate
• 英文别名: [(2S)-4-phenylbutan-2-yl] butanoate
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: PNESWLOWEKZEIH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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2,2,2-三氟乙酯 、 4-苯基-2-丁醇 在 aminocyclopentadienylruthenium surfacant-treated subtilisin 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以95%的产率得到(S)-4-phenyl-2-butyl butyrate
  参考文献：
  名称：

  (S)-Selective Dynamic Kinetic Resolution of Secondary Alcohols by the Combination of Subtilisin and an Aminocyclopentadienylruthenium Complex as the Catalysts

  摘要：

  A new procedure for the dynamic kinetic resolution (DKR) of racemic alcohols into single enantiomers is described. This procedure employs surfactant-treated subtilisin as an (S)-selective resolving catalyst and an aminocyclopentadienylruthenium complex as a racemizing catalyst. The DKR is performed best in the presence of an acyl donor such as trifluoroethyl butyrate in THF at room temperature. Eight simple secondary alcohols have been efficiently resolved with high optical purities and good yields. The subtilisin-based DKR is complementary in stereoselectivity to its lipase-based counterpart. For an acyl-carrying alcohol, both subtilisin- and lipase-based DKRs have proceeded equally well to give a pair of enantiomeric products (>99.5% ee each) with opposite optical rotations in high yields (94-95%).

  DOI：

  10.1021/ja036766r

文献信息

• 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
• Functional expression of Serratia marcescens H30 lipase in Escherichia coli for efficient kinetic resolution of racemic alcohols in organic solvents
  作者：Erzheng Su、Jingjing Xu、Pengyong You

  DOI：10.1016/j.molcatb.2014.04.012

  日期：2014.8

  A lipase from Serratia marcescens H30 was cloned and functionally expressed in E. coli in soluble form (more than 80%). The recombinant lipase activity reached 25,000 U/L after optimization. Different carriers were used to immobilize the recombinant S. marcescens lipase (SmL), and LH-EP was found to be the most ideal carrier. LH-EP immobilized SmL could catalyze enantioselective resolution of racemic alcohols. Using 4-phenyl-2-butanol as the model alcohol, the effects of temperature, organic solvent, water activity, acyl donor and substrate molar ratio on the LH-EP immobilized SmL catalyzed kinetic resolution were investigated. All of these factors influenced the resolution effect to some extent. At last, a high E value of more than 200 was achieved, with ee(s) > 99% and a conversion of 49.9%. Further studies showed that the LH-EP immobilized SmL could also catalyze the kinetic resolution of other structure similar racemic alcohols. These results indicate that the SmL is useful for biocatalytic production of chiral alcohols. This work is the first attempt of using SmL in this field, and it further broadens the application field of SmL. (C) 2014 Elsevier B.V. All rights reserved.
• (<i>S</i>)-Selective Dynamic Kinetic Resolution of Secondary Alcohols by the Combination of Subtilisin and an Aminocyclopentadienylruthenium Complex as the Catalysts
  作者：Mahn-Joo Kim、Yong Il Chung、Yoon Kyung Choi、Han Ki Lee、Daeho Kim、Jaiwook Park

  DOI：10.1021/ja036766r

  日期：2003.9.1

  A new procedure for the dynamic kinetic resolution (DKR) of racemic alcohols into single enantiomers is described. This procedure employs surfactant-treated subtilisin as an (S)-selective resolving catalyst and an aminocyclopentadienylruthenium complex as a racemizing catalyst. The DKR is performed best in the presence of an acyl donor such as trifluoroethyl butyrate in THF at room temperature. Eight simple secondary alcohols have been efficiently resolved with high optical purities and good yields. The subtilisin-based DKR is complementary in stereoselectivity to its lipase-based counterpart. For an acyl-carrying alcohol, both subtilisin- and lipase-based DKRs have proceeded equally well to give a pair of enantiomeric products (>99.5% ee each) with opposite optical rotations in high yields (94-95%).