1-(3-溴苯基)乙酸乙酯 | 6948-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-溴苯基)乙酸乙酯
• 英文名称: (+/-)-1-(3-bromophenyl)ethyl acetate
• 英文别名: 3-Brom-1-<1-acetoxy-ethyl>-benzol；1-<3-Brom-phenyl>-aethyl-acetat；Essigsaeure-1-(o-brom-phenyl)-aethylester；1-(3-Brom-phenyl)-aethyl-acetat；1-(3-Bromophenyl)ethyl acetate
• CAS: 6948-02-3
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: KOVFPCQHFMIZJO-UHFFFAOYSA-N

物化性质

• 沸点：
  268.8±15.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1-(3-溴苯基)乙酸乙酯 在 phosphate buffer 作用下， 以 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 [(1S)-1-(3-bromophenyl)ethyl] acetate 、 (R)-3-溴-alpha-甲基苄醇
  参考文献：
  名称：

  Screening of liver acetone powders in the resolution of 1-phenylethanols and 1-phenylpropanols derivatives

  摘要：

  Hydrolases from the liver acetone powders (LAPs) of bovine, cat, chicken, turkey, lamb, pig, rabbit, and rat were assessed for the enantioselective hydrolysis of acetates of 1-(4-chlorophenyl)ethanot, 1-(3-bromophenyl)ethanol, 1-(4-chlorophenyl)propanol, 1-(4-bromophenyl)propanol, and 1-(3-bromophenyl)propanol. The enantioselectivity of the hydrolytic reaction was dependent upon the liver hydrolase, substrate, pH of the reaction media, and the cosolvent. The most ester selective LAP was from chicken, and the resulting alcohols had the highest ee (80% to >99%). All of the LAPs tested catalyzed the hydrolysis of 1-(4-chlorophenyl)ethanol, except for lamb LAP. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.041
• 作为产物：
  描述：

  1-(3-溴苯基)乙醇 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3-溴苯基)乙酸乙酯
  参考文献：
  名称：

  Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols

  摘要：

  The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.018

文献信息

• Superacid BF₃–H₂O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
  作者：Shuting Zhang、Xiaohui Zhang、Xuege Ling、Chao He、Ruofeng Huang、Jing Pan、Jiaqiang Li、Yan Xiong

  DOI：10.1039/c4ra04059g

  日期：——

  An efficient in situ prepared superacid BF₃–H₂O promoted benzylation of arenes using benzyl alcohols and acetates achieves various diarylalkanes.

  一种高效的原位制备的超强酸BF3-H2O促进的芳烃苄基化反应，使用苄醇和醋酸酯制备各种二芳基烷烃。
• Concerted bimolecular substitution reactions of 1-phenylethyl derivatives
  作者：John P. Richard、William P. Jencks

  DOI：10.1021/ja00317a033

  日期：1984.3

  Etude des proprietes des reactions de substitution bimoleculaire des derives aryl-1 ethyles avec l'azoture et d'autres reactifs nucleophiles

  Etude des proprietes des反应去取代双分子衍生芳基-1 乙基酯 avec l'azoture et d'autres reactifs 亲核试剂
• Solvolysis of 1-arylethyl tosylates. Kinetic and stereochemical tests for solvent participation
  作者：Annette D. Allen、V. M. Kanagasabapathy、Thomas T. Tidwell

  DOI：10.1021/ja00301a023

  日期：1985.7

  Les etudes de solvolyses des tosylates d'aryl-1ethyles (aryl=bromo-3phenyl, trifluoromethyl-3 phenyl et bis-trifluoromethyl-3,5phenyl) montrent que dans des solvants relativement non nucleophiles, les trois substrats ont des vitesses polarimetriques plus rapides que les vitesses de formation des produits

  Les etudes de solvolyses des tosylates d'aryl-1ethyles (aryl=bromo-3phenyl, trifluoromethyl-3 phenyl et bis-trifluoromethyl-3,5phenyl) montrent que dans des solvants relativement non nucleophiles, les trois substrats ont des vitesses polarimetriques les vitesses deformation des produits
• Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols
  作者：Luciana L. Machado、Telma L.G. Lemos、Marcos Carlos de Mattos、Maria da Conceicão F. de Oliveira、Gonzalo de Gonzalo、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.05.018

  日期：2008.6

  The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst. (C) 2008 Elsevier Ltd. All rights reserved.
• Screening of liver acetone powders in the resolution of 1-phenylethanols and 1-phenylpropanols derivatives
  作者：Aida Solís、Susana García、Herminia I. Pérez、Norberto Manjarrez、Héctor Luna

  DOI：10.1016/j.tetasy.2008.01.041

  日期：2008.3

  Hydrolases from the liver acetone powders (LAPs) of bovine, cat, chicken, turkey, lamb, pig, rabbit, and rat were assessed for the enantioselective hydrolysis of acetates of 1-(4-chlorophenyl)ethanot, 1-(3-bromophenyl)ethanol, 1-(4-chlorophenyl)propanol, 1-(4-bromophenyl)propanol, and 1-(3-bromophenyl)propanol. The enantioselectivity of the hydrolytic reaction was dependent upon the liver hydrolase, substrate, pH of the reaction media, and the cosolvent. The most ester selective LAP was from chicken, and the resulting alcohols had the highest ee (80% to >99%). All of the LAPs tested catalyzed the hydrolysis of 1-(4-chlorophenyl)ethanol, except for lamb LAP. (C) 2008 Elsevier Ltd. All rights reserved.