(R)-ibuprofen hexyl ester | 292620-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-ibuprofen hexyl ester
• 英文别名: Hexyl (I+/-R)-I+/--methyl-4-(2-methylpropyl)benzeneacetate；hexyl (2R)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 292620-87-2
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: LLTNCZLHUNOWNU-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  布洛芬 、 正己醇 在 Rhizomucor mehei lipase immobilized on acrylic resin beads 作用下， 以 甲基叔丁基醚 为溶剂， 反应 30.0h， 以93.78%的产率得到
  参考文献：
  名称：

  固定化的Novozym40086在有机相中催化（R，S）-布洛芬的拆分。

  摘要：

  Novozym40086催化的布洛芬对映选择性酯化反应在有机溶剂中成功进行。将去除水试剂添加到反应混合物中以去除酯化反应中产生的水。研究了温度，正己醇浓度，布洛芬浓度和酶载量的影响。在平衡条件下，得到的热力学平衡常数（K）为7.697，对映选择性（E）为8.512。酯化反应在约30小时内达到平衡，转化率为56％，ee S为93.78％。X和ee S的预测值分别为67.90％和95.60％。实验值近似等于理论值，表明理想模型的可行性。

  DOI：

  10.1002/chir.23070

文献信息

• Improvements of enzyme activity and enantioselectivity in lipase-catalyzed alcoholysis of (R,S)-azolides
  作者：An-Chi Wu、Pei-Yun Wang、Yi-Sheng Lin、Min-Fang Kao、Jin-Ru Chen、Jyun-Fen Ciou、Shau-Wei Tsai

  DOI：10.1016/j.molcatb.2009.11.001

  日期：2010.3

  With Candida antarctica lipase B (CALB)-catalyzed alcoholysis of (R,S)-naproxenyl 1,2,4-triazolide at the optimal conditions (i.e. anhydrous MTBE as the solvent, and methanol as the acyl acceptor at 45 degrees C) as the model system, the enzyme enantioselectivity in terms of V-R/V-S = 105.8 and specific activity for the fast-reacting (R)-azolide V-R/(E-t) = 0.979 mmol/(h g) were greatly improved in comparison with V-R/V-S = 8.0 and V-R/(E-t) = 0.113 mmol/(h g) of using (R,S)-naproxenyl 2,2,2-trifluoroethyl ester as the substrate. The resolution strategy was successfully extended to other (R,S)-profenyl 1,2,4-triazolides and lipases from Candida rugosa (Lipase MY) and Carica papaya (CPL) having opposite enantioselectivity to CALB. Moreover, the kinetic constants were estimated, compared with those obtained via hydrolysis, and employed for modeling time-course conversions of (R,S)-naproxenyl 1,2,4-triazolide in anhydrous MTBE. The advantages of easy substrate preparation, high enzyme reactivity and enantioselectivity, as well as easy product separation from the remaining substrate via reactive extraction demonstrate merits of using (R,S)-azolides but not the corresponding esters for the alcoholytic resolution. (C) 2009 Elsevier B.V. All rights reserved.
• Lipase-Catalyzed Resolution of Ibuprofen
  作者：Erik Henke、Sascha Schuster、Hong Yang、Uwe T. Bornscheuer

  DOI：10.1007/s007060070091

  日期：2000.6.15

  The resolution of ibuprofen by transesterification of its corresponding vinylester using lipase B from Candida antarctica is described. Compared to transesterification or hydrolysis of the ibuprofen ethyl ester (E < 2, 28-48 h), the reaction with vinylesters occurred significantly faster (1.5-5 h) and with considerably higher enantioselectivity (E = 8-39).
• Resolution of ( <i>R</i> , <i>S</i> )‐ibuprofen catalyzed by immobilized Novozym40086 in organic phase
  作者：Xin Yuan、Lujun Wang、Guangyong Liu、Guilin Dai、Kewen Tang

  DOI：10.1002/chir.23070

  日期：2019.6

  The enantioselective esterification of ibuprofen catalyzed by Novozym40086 was successfully conducted in organic solvent. Removing‐water reagent was added into the reaction mixture to remove water produced in the esterification. The effects of temperature, n‐hexanol concentration, ibuprofen concentration, and loading of enzymes were investigated. Under the condition of equilibrium, the thermodynamic

  Novozym40086催化的布洛芬对映选择性酯化反应在有机溶剂中成功进行。将去除水试剂添加到反应混合物中以去除酯化反应中产生的水。研究了温度，正己醇浓度，布洛芬浓度和酶载量的影响。在平衡条件下，得到的热力学平衡常数（K）为7.697，对映选择性（E）为8.512。酯化反应在约30小时内达到平衡，转化率为56％，ee S为93.78％。X和ee S的预测值分别为67.90％和95.60％。实验值近似等于理论值，表明理想模型的可行性。