(R)-1-phenylpentyl propionate | 138309-00-9

• 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-phenylpentyl propionate
• CAS: 138309-00-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XZZSXUUJYIBQKT-CYBMUJFWSA-N

物化性质

• 沸点：
  285.3±9.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-phenyloctan-3-one 在 D-葡萄糖-6-磷酸 、 Leuconostoc mesenteroides glucose-6-phosphate dehydrogenase 、 Thermobifida fusca recombinant phenylacetone monooxygenase 、 NADPH 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-4-phenyloctan-3-one 、 (R)-4-phenyloctan-3-one 、 (S)-1-phenylpentyl propionate 、 (R)-1-phenylpentyl propionate
  参考文献：
  名称：

  Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.03.018