4-(2,4-Dichlorophenyl)-2-oxobutanoic acid | 1260521-21-8

• 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: 4-(2,4-Dichlorophenyl)-2-oxobutanoic acid
• 英文别名: 4-(2,4-dichlorophenyl)-2-oxobutanoic acid
• CAS: 1260521-21-8
• 化学式: C₁₀H₈Cl₂O₃
• 分子量: 247.078
• InChiKey: JOMCCTQKPLCULW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,4-Dichlorophenyl)-2-oxobutanoic acid 在 [RuCl(benzene)(S)-SunPhos]Cl 、 氢溴酸 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 70.0 ℃ 、2.76 MPa 条件下， 反应 20.0h， 生成 (2S)-4-(2,4-dichlorophenyl)-2-hydroxybutanoic acid
  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
• 作为产物：
  描述：

  2,4-二氯苯乙基溴 在 magnesium 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.5h， 生成 4-(2,4-Dichlorophenyl)-2-oxobutanoic acid
  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 hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids
  作者：Lufeng Zhu、Houhe Chen、Qinghua Meng、Weizheng Fan、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1016/j.tet.2011.06.071

  日期：2011.8

  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.