benzyl 2-bromo-2-(p-tolyl)acetate | 530091-80-6

• 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: benzyl 2-bromo-2-(p-tolyl)acetate
• 英文别名: benzyl 2-bromo-2-(4-methylphenyl)acetate
• CAS: 530091-80-6
• 化学式: C₁₆H₁₅BrO₂
• 分子量: 319.198
• InChiKey: OQUYJEDPWBZYLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  辛醇 、 benzyl 2-bromo-2-(p-tolyl)acetate 在 Pseudomonas cepacia lipase 作用下， 以 正辛烷 为溶剂， 反应 120.0h， 生成 benzyl (S)-2-bromo-2-(p-tolyl)acetate 、 benzyl (R)-2-bromo-2-(p-tolyl)acetate 、 octyl (S)-2-bromo-2-(p-tolyl)acetate 、 octyl (R)-2-bromo-2-(p-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
• 作为产物：
  描述：

  2-hydroxy-2-(4-methylphenyl)acetonitrile 在 盐酸 、 硫酸 、 氢溴酸 、 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 反应 15.0h， 生成 benzyl 2-bromo-2-(p-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

• Visible‐Light‐Induced Bromination of α‐Diazo Compounds with Bromoform
  作者：Xin Zhang、Junyue Lin、Miao‐Chang Liu、Yun‐Bing Zhou、Hua‐Yue Wu

  DOI：10.1002/ejoc.202300958

  日期：2024.1.22

  A visible-light-induced bromination of α-diazo compounds by using bromoform as bromine source was developed, providing a green synthetic route to α-bromoesters. This protocol features no use of a photocatalyst or an additive, and a broad substrate scope. Its practicality was demonstrated by the gram-scale reaction and several valuable follow-up transformations.

  开发了以三溴甲烷为溴源的可见光诱导α-重氮化合物溴化反应，为α-溴酯的绿色合成提供了一条途径。该方案的特点是不使用光催化剂或添加剂，且底物范围广泛。克级反应和几个有价值的后续转化证明了其实用性。
• 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.