(R)-ibuprofen isopropyl ester | 160496-23-1

• 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 isopropyl ester
• 英文别名: 1-Methylethyl (I+/-R)-I+/--methyl-4-(2-methylpropyl)benzeneacetate；propan-2-yl (2R)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 160496-23-1
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: RVZWLHIFEPTVBC-CYBMUJFWSA-N

物化性质

• 沸点：
  316.3±11.0 °C(predicted)
• 密度：
  0.958±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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 、 异丙醇 在 Novozym 435 作用下， 以2.1%的产率得到
  参考文献：
  名称：

  Esterification of R/S-ketoprofen with 2-propanol as reactant and solvent catalyzed by Novozym® 435 at selected conditions

  摘要：

  The enzymatic esterification of R/S-ketoprofen with 2-propanol catalyzed with the commercial biocatalyst Novozym (R) 435 is addressed in this investigation. The low reaction rate registered in this reaction was investigated in terms of the effect of the alcohol on the physicochemical-enzymatic stability of the biocatalyst and the interaction of the substrates with the catalytic triad at a molecular level.The effect of contacting 2-propanol:H2O mixture on Novozym (R) 435 was investigated at 45 degrees C for an extended period of time (8 days). The mixture dissolves the polymethylmethacrylate (PMMA) that constitutes the support of the Candida antarctica B lipase (CALB). Additionally, the alcohol diffuses into the biocatalyst's beads remaining strongly adsorbed (the alcohol desorption is evidenced only upon heating at 187 degrees C) and altering the inner texture of the biocatalyst's beads. Additionally, 2-propanol modifies the secondary structure of the enzyme by decreasing the beta-sheet contribution and increasing the beta-turn structure. The molecular modeling of the interaction of R/S-ketoprofen and 2-propanol with the catalytic triad of the lipase provides evidences that the secondary alcohol exerts an important steric hindrance for the reaction to proceed. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.016

文献信息

• Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes
  作者：Feipeng Liu、Qinghua Bian、Jianyou Mao、Zidong Gao、Dan Liu、Shikuo Liu、Xueyang Wang、Yu Wang、Min Wang、Jiangchun Zhong

  DOI：10.1016/j.tetasy.2016.05.010

  日期：2016.8

  Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic alpha-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral alpha-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic alpha-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S) -ibuprofen (99:1 er) via hydrolysis and recrystallization. (C) 2016 Elsevier Ltd. 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).
• Esterification of R/S-ketoprofen with 2-propanol as reactant and solvent catalyzed by Novozym® 435 at selected conditions
  作者：María Victoria Toledo、Carla José、Sebastián E. Collins、Rita D. Bonetto、María Luján Ferreira、Laura E. Briand

  DOI：10.1016/j.molcatb.2012.06.016

  日期：2012.11

  The enzymatic esterification of R/S-ketoprofen with 2-propanol catalyzed with the commercial biocatalyst Novozym (R) 435 is addressed in this investigation. The low reaction rate registered in this reaction was investigated in terms of the effect of the alcohol on the physicochemical-enzymatic stability of the biocatalyst and the interaction of the substrates with the catalytic triad at a molecular level.The effect of contacting 2-propanol:H2O mixture on Novozym (R) 435 was investigated at 45 degrees C for an extended period of time (8 days). The mixture dissolves the polymethylmethacrylate (PMMA) that constitutes the support of the Candida antarctica B lipase (CALB). Additionally, the alcohol diffuses into the biocatalyst's beads remaining strongly adsorbed (the alcohol desorption is evidenced only upon heating at 187 degrees C) and altering the inner texture of the biocatalyst's beads. Additionally, 2-propanol modifies the secondary structure of the enzyme by decreasing the beta-sheet contribution and increasing the beta-turn structure. The molecular modeling of the interaction of R/S-ketoprofen and 2-propanol with the catalytic triad of the lipase provides evidences that the secondary alcohol exerts an important steric hindrance for the reaction to proceed. (C) 2012 Elsevier B.V. All rights reserved.