(R)-2-hydroxy-4-(4-fluorophenyl)butanoic acid

• 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: (R)-2-hydroxy-4-(4-fluorophenyl)butanoic acid
• 英文别名: (2R)-4-(4-fluorophenyl)-2-hydroxybutanoic acid
• 化学式: C₁₀H₁₁FO₃
• 分子量: 198.194
• InChiKey: JUWBMSDOTPWEDG-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟苯丙醇 在 ammonium hydroxide 、 Pseudomonas sp. lipase 、 硫酸 、 氯化铵 、 pyridinium chlorochromate 、 sodium nitrite 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 (R)-2-hydroxy-4-(4-fluorophenyl)butanoic acid
  参考文献：
  名称：

  乳酸菌对（杂）芳基-脂肪族α-羟基羧酸的生物催化外消旋化。通过氧化-还原序列进行

  摘要：

  一系列（杂）芳基-和（二）芳基-脂肪族α-羟基羧酸的生物催化外消旋化已通过使用乳杆菌属的整个静息细胞实现。基本上温和的（生理）反应条件确保抑制不需要的副反应，例如消除、分解或缩合。使用副干酪乳杆菌 DSM 20207 无细胞提取物的辅因子/抑制剂研究表明，添加氧化还原辅因子 (NAD+/NADH) 导致外消旋化率明显增加，而在存在硫代-NAD+ 的情况下观察到强烈的抑制作用，这表明外消旋化是通过氧化还原序列进行的，而不是“外消旋酶”的参与。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600454

文献信息

• Anthelmintic depsipeptide compounds
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：US10793604B2

  公开（公告）日：2020-10-06

  The present invention provides cyclic depsipeptide compounds of formula (I) and compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

  本发明提供了对危害动物的寄生虫有效的式(I)环状去肽化合物和包含该化合物的组合物。这些化合物和组合物可用于防治哺乳动物和鸟类体内或身上的寄生虫。本发明还提供了一种根除、控制和预防鸟类和哺乳动物体内寄生虫侵扰的改进方法。
• 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。
• 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.
• 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.
• ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：US20190307838A1

  公开（公告）日：2019-10-10

  The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy 1 , Cy 2 , R 1 , R 2 , R 3 , R 4 , R a and R b is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.