(2S)-2-hydroxy-4-(4-methylphenyl)butanoic acid | 1327337-57-4

• 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: (2S)-2-hydroxy-4-(4-methylphenyl)butanoic acid
• CAS: 1327337-57-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ZDHZUIGLHDCERY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 (2S)-2-hydroxy-4-(4-methylphenyl)butanoic acid 在 硫酸 作用下， 反应 5.0h， 生成 (S)-2-Hydroxy-4-p-tolyl-butyric acid ethyl ester
  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：

  4-(p-methylphenyl)-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)-2-hydroxy-4-(4-methylphenyl)butanoic 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

• Siteselective and Enantiocomplementary C(sp³)–H Oxyfunctionalization for Synthesis of α-Hydroxy Acids
  作者：Xin Lian、Yingle Mao、Zunyun Fu、Weijie Zhang、Jiayan Chen、Dan Zhuo、Mingyue Zheng、Jiewei Wu、Cangsong Liao

  DOI：10.1021/acscatal.4c00398

  日期：2024.4.5

  Oxyfunctionalization of abundant carboxylic acids represents a direct approach to synthesizing α-hydroxy acids, which are valuable intermediates of various active pharmaceutical ingredients. Although ideal, the transformation is yet to be accomplished. Herein, enantiocomplementary C(sp3)–H oxyfunctionalization for the synthesis of α-hydroxy acids was realized by a cooperative strategy of substrate

  丰富的羧酸的氧官能化代表了合成α-羟基酸的直接方法，α-羟基酸是各种活性药物成分的有价值的中间体。尽管理想，但转变尚未完成。在此，通过α-酮戊二酸依赖性非血红素芳氧基链烷酸铁双加氧酶的底物工程、同源物筛选和蛋白质工程的合作策略，实现了用于合成α-羟基酸的对映互补C( sp 3 )–H氧官能化。该反应为三种67种α-羟基酸提供了简洁的合成路线，具有高效率和选择性（产率高达90%，ee高达>99%）。这些独特的互补反应丰富了生物催化氧官能化反应的种类。
• 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.