Butyric acid (E)-(R)-1-methyl-3-phenyl-allyl ester | 124219-14-3

• 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: Butyric acid (E)-(R)-1-methyl-3-phenyl-allyl ester
• 英文别名: [(E,2R)-4-phenylbut-3-en-2-yl] butanoate
• CAS: 124219-14-3
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: LJNBFCDLDJDSME-HCRIHEDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  正丁酸乙烯酯 、 ethyl (E)-1-phenylbut-1-en-3-ol 在 Burkholderia cepacia lipase 、 C₃₆H₇₃O₁₄S^(1-)*C₇H₁₀N⁽¹⁺⁾ 作用下， 反应 0.33h， 生成 Butyric acid (E)-(R)-1-methyl-3-phenyl-allyl ester
  参考文献：
  名称：

  Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid

  摘要：

  Three types of pyridinium salts, i.e., 1-ethylpyridin-1-ium cetyl-PEG(10) sulfate (PYET), 1-butylpyridin-1-ium cetyl-PEG(10) sulfate (PYBU), and 1-(3-methoxypropyl)pyridin-1-ium cetyl-PEG(10) sulfate (PYMP), have been prepared and evaluated for their activation property of Burkholderia cepacia lipase by comparison to the control IL-coated enzymes, 1-butyl-2,3-dimethylimidazolium cetyl-PEG(10) sulfate-coated lipase PS (1L1-PS). Among the tested pyridinium salt-coated lipases, the PYET-coated lipase PS (PYET-PS) exhibited the best results; the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, 1-(pyridin-4-yl)ethanol, or 4-phenylbut-3-en-2-ol proceeded faster than those of the IL1-PS-catalyzed reaction while maintaining an excellent enantioselectivity (E > 200). This improved efficiency was found to be dependent on the increased K-cat value. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.12.028

文献信息

• Enzyme reactions in apolar solvent. 5. The effect of adjacent unsaturation on the porcine pancreatic lipase catalyzed kinetic resolution of secondary alcohols
  作者：Brian Morgan、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1021/jo00037a049

  日期：1992.5

  The effect of adjacent unsaturation on the enzyme-catalyzed kinetic resolution of secondary alcohols is studied for a series of allylic, homoallylic, propargylic, homopropargylic, and phenyl-substituted 2-alkanols, using porcine pancreatic lipase (PPL) in anhydrous Et2O. Excellent enantioselectivity (high E value) was observed for alpha-phenethyl alcohol (3), propargylic alcohols (8 and 11), and (E)-allylic alcohols (9 and 12), but (Z)-allylic alcohols (10 and 13) showed poor selectivity. Enantioselectivity was also low for both (E)- and (Z)-homoallylic alcohols (15 and 16), homopropargylic alcohol (14), I-phenyl-2-propanol (6), and 4-phenyl-2-butanol (7). The enhanced enantioselectivity observed for (E)-allylic alcohols was exploited in the synthesis of the enantiomers of both components of the aggregation pheromone of the lesser grain borer, Rhyzopertha dominica (F.). The magnitude of the enantiomeric ratio (E value) can be dramatically affected by the accuracy of the values of ee(s) and ee(p) used in the calculation, especially when E is large. Variation in the value of E with the optical purity of the chiral derivatizing agent used to determine ee(s) and ee(p) is illustrated.