(S)-4-(2,4-dichloro)-phenyl-2-hydroxybutanoic acid ethyl ester | 1058856-50-0

• 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: (S)-4-(2,4-dichloro)-phenyl-2-hydroxybutanoic acid ethyl ester
• 英文别名: ethyl (2S)-4-(2,4-dichlorophenyl)-2-hydroxybutanoate
• CAS: 1058856-50-0
• 化学式: C₁₂H₁₄Cl₂O₃
• 分子量: 277.147
• InChiKey: ARSVLNMCGVZGBX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二氯苯乙基溴 在 硫酸 、 [RuCl(benzene)(S)-SunPhos]Cl 、 氢溴酸 、 氢气 、 magnesium 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， -10.0~80.0 ℃ 、2.76 MPa 条件下， 反应 28.5h， 生成 (S)-4-(2,4-dichloro)-phenyl-2-hydroxybutanoic acid ethyl ester
  参考文献：
  名称：

  Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids

  摘要：

  The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%-92.6% ee) and efficiency (TON=10,000, TOF=300 h(-1)) make this method efficient for the synthesis of an important intermediate, (R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.071

文献信息

• Highly Enantioselective Sequential Hydrogenation of Ethyl 2-Oxo-4-arylbut-3-enoate to Ethyl 2-Hydroxy-4-arylbutyrate
  作者：Qinghua Meng、Lufeng Zhu、Zhaoguo Zhang

  DOI：10.1021/jo801140j

  日期：2008.9.19

  The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2](+)[RuCl [(S)-SunPhos]}2(mu-Cl-3] gave ethyl 2-hydroxy-4-arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C = O and C = C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81 % yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.
• Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids
  作者：Lvfeng Zhu、Qinghua Meng、Weizheng Fan、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/jo101084t

  日期：2010.9.3

  A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3-enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h(-1)), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors.