(S)-ibuprofen isopropyl ester

• 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: (S)-ibuprofen isopropyl ester
• 英文别名: propan-2-yl 2-[4-(2-methylpropyl)phenyl]propanoate；(S)-iso-propyl 2-(4-isobutylphenyl)propanoate；Dexibuprofen Isopropyl Ester；propan-2-yl (2S)-2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: RVZWLHIFEPTVBC-ZDUSSCGKSA-N

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：

  (S)-(+)-布洛芬 、 异丙醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(S)-ibuprofen isopropyl ester
  参考文献：
  名称：

  右布洛芬酯和酰胺前药的合成，表征和体外水解研究

  摘要：

  已经合成了十个具有酯和酰胺部分而不是游离羧酸的地布洛芬前药，其涉及胃肠道副作用。将地布洛芬酰氯与不同的氨基酸甲酯盐酸盐和五种醇缩合，得到酰胺和酯前药。所有合成的前药均通过mp，R f，元素分析，FTIR，1 H NMR和13表征13 C NMR光谱。血浆中的体外水解研究表明，由于化学结构不同，前药在水解反应方面也有所不同。在烷基取代中，支链烷基取代基或芳族取代基提高了亲脂性，但降低了溶解度和水解速率。具有支链和芳族取代的酰胺前药也可以考虑持续释放。与地布洛芬相比，前药对胃粘膜的刺激​​性较小。

  DOI：

  10.1007/s00044-011-9866-z

文献信息

• A Practical New Chiral Controller for Asymmetric Diels−Alder and Alkylation Reactions
  作者：Georgios Sarakinos、E. J. Corey

  DOI：10.1021/ol991007s

  日期：1999.12.1

  prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55 degrees C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted

  通过简单实用的方法由1，2-环氧环己烷制备对映体纯的羟基砜（+）-和（-）-2。这些醇的丙烯酸酯在CH2Cl2或C7H8中于-78至-55摄氏度下，具有多种二烯，经BCl3催化的Diels-Alder反应，具有各种不同的二烯，具有高的亲二烯体选择性（表1）。如此形成的手性酯很容易裂解，并得到控制剂（+）-或（-）-2。（+）-和（-）-2的酯可以转化为Z-钾烯醇盐并以高表面选择性被烷基化。
• 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.
• 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.
• 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).
• Synthesis, characterization and in vitro hydrolysis studies of ester and amide prodrugs of dexibuprofen
  作者：Zaman Ashraf、Muhammad Imran、Shahid Amin

  DOI：10.1007/s00044-011-9866-z

  日期：2012.11

  The in vitro hydrolysis studies in plasma reflect prodrugs have been varied in terms of reactivity toward hydrolysis, owing to the different chemical structures. In alkyl substitution the branched chain alkyl substituents or aromatic substituents resulted in enhanced lipophilicity but diminished dissolution and hydrolysis rate. The amide prodrugs with branched and aromatic substitution can also be considered

  已经合成了十个具有酯和酰胺部分而不是游离羧酸的地布洛芬前药，其涉及胃肠道副作用。将地布洛芬酰氯与不同的氨基酸甲酯盐酸盐和五种醇缩合，得到酰胺和酯前药。所有合成的前药均通过mp，R f，元素分析，FTIR，1 H NMR和13表征13 C NMR光谱。血浆中的体外水解研究表明，由于化学结构不同，前药在水解反应方面也有所不同。在烷基取代中，支链烷基取代基或芳族取代基提高了亲脂性，但降低了溶解度和水解速率。具有支链和芳族取代的酰胺前药也可以考虑持续释放。与地布洛芬相比，前药对胃粘膜的刺激​​性较小。