Acetic acid (R)-1-methyl-4-phenyl-butyl ester | 129098-45-9

• 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: Acetic acid (R)-1-methyl-4-phenyl-butyl ester
• CAS: 129098-45-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: JQPHHXBUNQEQDJ-LLVKDONJSA-N

物化性质

• 沸点：
  295.9±19.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 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：

  乙酸乙烯酯 、 4-苯基-2-丁醇 在 I₂₈₇C mutant of Burkholderia cepacia NBRC 14595 lipase bearing an N-phenylacetamide (PAA) moiety immobilized on Toyonite 200M 作用下， 以 异丙醚 为溶剂， 反应 5.5h， 以78.5%的产率得到
  参考文献：
  名称：

  Chemical Modification of Lipase for Rational Enhancement of Enantioselectivity

  摘要：

  对洋葱伯克霍尔德菌脂肪酶的I287C突变体进行化学修饰，得到了多种I287C-X偶联物，其中含有N-苯乙酰胺（PAA）基团的I287C-PAA表现出优异的非对映选择性和催化二级醇的活性。定点化学修饰是控制非对映选择性生物催化的有力工具。

  DOI：

  10.1246/cl.150667

文献信息

• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.