(2S)-4-(1,3-benzodioxol-5-yl)-2-hydroxybutanoic acid | 1327337-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2S)-4-(1,3-benzodioxol-5-yl)-2-hydroxybutanoic acid
• CAS: 1327337-59-6
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: RZNFSVIJGZDMBS-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 (2S)-4-(1,3-benzodioxol-5-yl)-2-hydroxybutanoic acid 在 硫酸 作用下， 反应 5.0h， 生成 ethyl (2S)-4-(1,3-benzodioxol-5-yl)-2-hydroxybutanoate
  参考文献：
  名称：

  Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids

  摘要：

  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.

  DOI：

  10.1021/jo101084t
• 作为产物：
  描述：

  5-(2-bromoethyl)-1,3-benzodioxole 在 [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 23.5h， 生成 (2S)-4-(1,3-benzodioxol-5-yl)-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

文献信息

• 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.
• 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.