(2-甲基-3-苯基丙基)丁酸酯 | 652984-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-甲基-3-苯基丙基)丁酸酯
• 英文名称: (+/-)-2-methyl-3-phenyl-1-propyl butanoate
• 英文别名: (+/-)-3-phenyl-2-methyl-1-propyl butyrate；2-Methyl-3-phenylpropyl butanoate；(2-methyl-3-phenylpropyl) butanoate
• CAS: 652984-31-1
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: YBSUKZUKFZUWMA-UHFFFAOYSA-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

• 作为反应物：
  描述：

  (2-甲基-3-苯基丙基)丁酸酯 在 phosphate buffer 、 Pseudomonas cepacia lipase 作用下， 反应 2.0h， 生成 (S)-2-methyl-3-phenylpropan-1-ol 、 (R)-2-methyl-3-phenyl-1-propyl butanoate
  参考文献：
  名称：

  A drop of enantioselectivity in the Pseudomonas cepacia lipase-catalyzed ester hydrolysis is influenced by the chain length of the fatty acid

  摘要：

  A two-step molecular mechanics based computational procedure has been applied to explain the enantioselectivity observed in the hydrolysis of esters of primary alcohols, carried out in the presence of a lipase from Pseudomonas cepacia. This approach proved to be very effective in explaining an unpredictable drop in enantioselectivity, experimentally observed when the chain of the fatty acid was lengthened and to predict the chain length in correspondence of which the effect should have revealed itself. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.010
• 作为产物：
  描述：

  2-甲基-3-苯基丙醛 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2-甲基-3-苯基丙基)丁酸酯
  参考文献：
  名称：

  Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)-CH2OH by Pseudomonas cepacia lipase: effect of acyl chain length and solvent

  摘要：

  Although lipase from Pseudomonas cepacia (PCL) shows high enantioselectivity towards many secondary alcohols, it usually exhibits only low to moderate enantioselectivity towards primary alcohols. To increase this enantioselectivity, we optimised the reaction conditions for the PCL-catalysed hydrolysis of esters of three chiral primary alcohols: 2-methyl-3-phenyl-1-propanol 1, 2-phenoxy-1-propanol 2 and solketal 3. The enantioselectivity towards 1-acetate increased from E=16 to 38 upon changing the solvent from ethyl ether/phosphate buffer to 30% n-propanol in phosphate buffer and increased again to E greater than or equal to 190 upon changing the substrate from 1-acetate to 1-heptanoate. The same changes increased the enantioselectivity towards alcohol 2 from E=17 to 70, but did not significantly increase the enantioselectivity towards alcohol 3. The best solvent was similar to the solvent used to crystallise the open form of PCL and likely stabilises the open form of PCL. This stabilisation may increase the enantioselectivity by removing kinetic contributions from a non-enantioselective lid-opening step. We determined the kinetic contribution of the lid-opening step by measuring the interfacial activation of PCL. The activation energy for the PCL-catalysed hydrolysis of ethyl acetate was at least 2.6 kcal/mol lower in the presence of a water-organic solvent interface. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.049

文献信息

• Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)-CH2OH by Pseudomonas cepacia lipase: effect of acyl chain length and solvent
  作者：Alessandra Mezzetti、Curtis Keith、Romas J. Kazlauskas

  DOI：10.1016/j.tetasy.2003.09.049

  日期：2003.12

  Although lipase from Pseudomonas cepacia (PCL) shows high enantioselectivity towards many secondary alcohols, it usually exhibits only low to moderate enantioselectivity towards primary alcohols. To increase this enantioselectivity, we optimised the reaction conditions for the PCL-catalysed hydrolysis of esters of three chiral primary alcohols: 2-methyl-3-phenyl-1-propanol 1, 2-phenoxy-1-propanol 2 and solketal 3. The enantioselectivity towards 1-acetate increased from E=16 to 38 upon changing the solvent from ethyl ether/phosphate buffer to 30% n-propanol in phosphate buffer and increased again to E greater than or equal to 190 upon changing the substrate from 1-acetate to 1-heptanoate. The same changes increased the enantioselectivity towards alcohol 2 from E=17 to 70, but did not significantly increase the enantioselectivity towards alcohol 3. The best solvent was similar to the solvent used to crystallise the open form of PCL and likely stabilises the open form of PCL. This stabilisation may increase the enantioselectivity by removing kinetic contributions from a non-enantioselective lid-opening step. We determined the kinetic contribution of the lid-opening step by measuring the interfacial activation of PCL. The activation energy for the PCL-catalysed hydrolysis of ethyl acetate was at least 2.6 kcal/mol lower in the presence of a water-organic solvent interface. (C) 2003 Elsevier Ltd. All rights reserved.
• A drop of enantioselectivity in the Pseudomonas cepacia lipase-catalyzed ester hydrolysis is influenced by the chain length of the fatty acid
  作者：Andrea Tafi、Fabrizio Manetti、Maurizio Botta、Silvana Casati、Enzo Santaniello

  DOI：10.1016/j.tetasy.2004.06.010

  日期：2004.8

  A two-step molecular mechanics based computational procedure has been applied to explain the enantioselectivity observed in the hydrolysis of esters of primary alcohols, carried out in the presence of a lipase from Pseudomonas cepacia. This approach proved to be very effective in explaining an unpredictable drop in enantioselectivity, experimentally observed when the chain of the fatty acid was lengthened and to predict the chain length in correspondence of which the effect should have revealed itself. (C) 2004 Elsevier Ltd. All rights reserved.