(+)-(R)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid butyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(R)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid butyl ester
• 英文别名: ketorolac butyl ester；butyl (1R)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: OBQFPYGIWUPAKT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  酮咯酸 、 正丁醇 在 对甲苯磺酸 、 sodium hydroxide 、 phosphate buffer 、 hydrolase from Streptomyces griseus 作用下， 以 苯 、 水 为溶剂， 反应 32.0h， 生成 (+)-(R)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid butyl ester
  参考文献：
  名称：

  Enzymatic kinetic resolution of ketorolac

  摘要：

  Ketorolac was resolved into each enantiomer by interesterification using lipase B from Candida antarctica. The acid reacted with various alcohols and the ester and acid were resolved up to > 99% e.e. when reacted with octanol, which was the best result. To increase reactivity and enantioselectivity, the experimental conditions were adjusted by varying temperature, solvent, alcohols and reaction time. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00332-9

文献信息

• Insight into microwave assisted immobilized Candida antarctica lipase B catalyzed kinetic resolution of RS-(±)-ketorolac
  作者：Somnath D. Shinde、Ganapati D. Yadav

  DOI：10.1016/j.procbio.2014.12.005

  日期：2015.2

  Abstract Microwave assisted biocatalytic transformation is a green process for chiral drug resolution. Different immobilized enzymes such as Novozym 435, Lipozyme TL IM, Lipozyme RM IM, Lipase Amano AS and Lipase AYS amino were screened for the kinetic resolution of RS-(±)-ketorolac under microwave irradiation. To study kinetics and mechanism, the effect of different parameters on the conversion, initial

  摘要 微波辅助生物催化转化是手性药物拆分的绿色工艺。筛选了不同的固定化酶，如 Novozym 435、Lipozyme TL IM、Lipozyme RM IM、Lipase Amano AS 和 Lipase AYS 氨基，用于在微波辐射下对 RS-(±)-酮咯酸的动力学分辨率进行筛选。为了研究动力学和机理，研究了不同参数对底物转化率、初始速率和对映体过量的影响。在微波协同作用下，观察到初始速率增加了 1.5 倍。Novozym 435 有效地催化了 RS-(±)-酮咯酸的对映选择性酯化，在 50 °C 和 300 rpm 下 3 小时内显示出优异的转化率 (50%) 和对映体过量 (>99%)。根据初始速率和进度曲线数据，
• Enzymatic kinetic resolution of ketorolac
  作者：Young Hee Kim、Chan Seong Cheong、So Ha Lee、Kwan Soo Kim

  DOI：10.1016/s0957-4166(01)00332-9

  日期：2001.7

  Ketorolac was resolved into each enantiomer by interesterification using lipase B from Candida antarctica. The acid reacted with various alcohols and the ester and acid were resolved up to > 99% e.e. when reacted with octanol, which was the best result. To increase reactivity and enantioselectivity, the experimental conditions were adjusted by varying temperature, solvent, alcohols and reaction time. (C) 2001 Published by Elsevier Science Ltd.