(R)-1-phenylbutyl propionate | 138308-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-phenylbutyl propionate
• CAS: 138308-99-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: QAEYBNKACOJJLV-GFCCVEGCSA-N

物化性质

• 沸点：
  267.4±9.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (+/-)-4-phenyl-heptan-3-one 在 glucose-6-phosphate 、 4-hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB 、 glucose-6-phosphate dehydrogenase from Leuconostoc mesenteroides 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 144.0h， 生成 (R)-4-phenylheptan-3-one 、 (S)-1-phenylbutyl propionate 、 (R)-1-phenylbutyl propionate 、 (S)-4-phenylheptan-3-one
  参考文献：
  名称：

  BVMO催化的外消旋的苄基酮的动态动力学拆分中的阴离子交换树脂的存在下†往最‡

  摘要：

  4-羟基苯乙酮来自荧光假单胞菌ACB的单加氧酶在弱阴离子交换树脂的存在下用于以高转化率和良好的光学纯度进行外消旋苄基酮的动态动力学拆分。为了优化生物催化系统的活性和选择性，分析了影响酶催化的拜耳-维利格氧化和外消旋化效率的不同参数。

  DOI：

  10.1039/b922693a

文献信息

• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.