ethyl (S)-2-bromo-2-(o-tolyl)acetate

• 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: ethyl (S)-2-bromo-2-(o-tolyl)acetate
• 英文别名: ethyl (2S)-2-bromo-2-(2-methylphenyl)acetate
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: WSHAGPCQJGMMGF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  辛醇 、 ethyl 2-bromo-2-(o-tolyl)acetate 在 Pseudomonas cepacia lipase 作用下， 以 正辛烷 为溶剂， 反应 120.0h， 生成 ethyl (R)-2-bromo-2-(o-tolyl)acetate 、 (S)-2-bromo-2-o-tolylacetic acid octyl ester 、 ethyl (S)-2-bromo-2-(o-tolyl)acetate 、 octyl (R)-2-bromo-2-(o-tolyl)acetate
  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

• 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.
• New efficient lipase from Yarrowia lipolytica for the resolution of 2-bromo-arylacetic acid esters
  作者：David Guieysse、Georgina Sandoval、Laeticia Faure、Jean-Marc Nicaud、Pierre Monsan、Alain Marty

  DOI：10.1016/j.tetasy.2004.09.008

  日期：2004.11

  A new extracellular lipase (Lip2p) from the yeast Yarrowia lipolytica was used for the resolution of 2-bromo-arylacetic acid esters, an important class of chemical intermediates for the pharmaceutical industry. Its efficiency for the transesterification of racemic mixtures with 1-octanol in n-octane was compared with the most efficient lipases described to date, lipases from Burkholderia cepacia and Rhizomucor miehei. Resolution of 2-bromo-p-tolylacetic acid ethyl ester catalyzed by Y. lipolytica lipase showed an enantio preference of 28, almost equal to that obtained with B. cepacia lipase (E = 30). Moreover, Y lipolytica lipase presents a higher catalytic activity and an (S)-enantiopreference, while B. cepacia lipase is (R)-enantiomer selective. The most interesting result is that Y lipolytica lipase has until now been the only enzyme able to catalyze the resolution of 2-bromo-o-tolylacetic acid ethyl ester (E = 27). (C) 2004 Elsevier Ltd. All rights reserved.