(R)-2-bromo-2-(o-tolyl)acetic acid

• 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: (R)-2-bromo-2-(o-tolyl)acetic acid
• 英文别名: (2R)-2-bromo-2-(2-methylphenyl)acetic acid
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: ADJAWAHSDBSEIY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydroxy-2-(2-methylphenyl)acetonitrile 在 盐酸 、 硫酸 、 氢溴酸 作用下， 以 水 为溶剂， 反应 15.0h， 生成 (R)-2-bromo-2-(o-tolyl)acetic acid
  参考文献：
  名称：

  Lipase-catalyzed enantioselective transesterification toward esters of 2-bromo-tolylacetic acids

  摘要：

  Lipases from Candida antarctica, Pseudomonas cepacia and Rhizomucor miehei were tested in the resolution of seven racemic substrates belonging to the (RS)-2-bromo tolyl acetate ester category, but differing either in the position of the methyl substituent on the acyl part of the aromatic ring, or in the structure of the alkyl group. Lipase-catalyzed kinetic resolution via transesterification reaction between the ester and octanol in octane revealed that, of the three enzymes tested, P. cepacia lipase is the most efficient for resolution of the various racemates, with R-enantiopreference. In addition, the position of the methyl substituent was found to play a key role in governing the enantioselectivity of the reaction. Using P. cepacia lipase and 2-bromo-in/p-tolyl- or 2-bromophenylacetic acid esters E-values of >50 were measured, whereas with the ortho derivatives, E-values dramatically decreased to <6. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00784-x

文献信息

• Enzymatic resolution of an alpha-substituted carboxylic acid or an ester thereof by Carica papaya lipase
  申请人：Tsai Shau-Wei

  公开号：US20060003428A1

  公开（公告）日：2006-01-05

  Disclosed herein is a process for enzymatically resolving a mixture of R- and S-enantiomers of an α-substituted carboxylic acid or an ester or thioester thereof, in which a Carica papaya lipase is used as a biocatalyst to effect the resolution as desired.

  本文公开了一种酶法分离α-取代羧酸或其酯或硫酯的R-和S-对映体混合物的方法，其中使用木瓜蛋白酶作为生物催化剂，以达到所需的分离效果。
• A variant of Yarrowia lipolytica lipase with improved activity and enantioselectivity for resolution of 2-bromo-arylacetic acid esters
  作者：Miguel Cancino、Philippe Bauchart、Georgina Sandoval、Jean-Marc Nicaud、Isabelle André、Valérie Dossat、Alain Marty

  DOI：10.1016/j.tetasy.2008.06.009

  日期：2008.7

  A variant of Lip2p lipase from Yarrowia lipolytica yeast was used for the resolution of 2-bromophenyl and o-tolyl acid esters, an important class of chemical intermediates for the pharmaceutical industry. In comparison with wild-type Lip2p, this variant, which contains one single amino acid change in the active site of the enzyme, V232A, displayed an enantioselectivity enhanced by one order of magnitude for the resolution of 2-bromo-phenylacetic acid ethyl ester (E-value increased from 5.5 to 59 for wild-type and V232A, respectively) and by fourfold for the resolution of 2-bromo-o-tolylacetic acid ethyl ester (going from an E-value of 27 to 111 for the wild-type and V232A, respectively). A remarkable increase in reaction velocity was also observed for both compounds, as a result of a significant gain in reactivity towards the favoured (S)-enantiomer (3- and 16-fold increase for 2-bromo-phenylacetic and -o-tolylacetic acid ethyl esters, respectively). These results demonstrate the key role of the V232 amino acid in enantiomer recognition and selectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• Lipase-catalyzed enantioselective transesterification toward esters of 2-bromo-tolylacetic acids
  作者：David Guieysse、Christophe Salagnad、Pierre Monsan、Magali Remaud-Simeon

  DOI：10.1016/s0957-4166(02)00784-x

  日期：2003.2

  Lipases from Candida antarctica, Pseudomonas cepacia and Rhizomucor miehei were tested in the resolution of seven racemic substrates belonging to the (RS)-2-bromo tolyl acetate ester category, but differing either in the position of the methyl substituent on the acyl part of the aromatic ring, or in the structure of the alkyl group. Lipase-catalyzed kinetic resolution via transesterification reaction between the ester and octanol in octane revealed that, of the three enzymes tested, P. cepacia lipase is the most efficient for resolution of the various racemates, with R-enantiopreference. In addition, the position of the methyl substituent was found to play a key role in governing the enantioselectivity of the reaction. Using P. cepacia lipase and 2-bromo-in/p-tolyl- or 2-bromophenylacetic acid esters E-values of >50 were measured, whereas with the ortho derivatives, E-values dramatically decreased to <6. (C) 2003 Elsevier Science Ltd. All rights reserved.