3-(2,4-二氯苯基)乳酸 | 68921-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(2,4-二氯苯基)乳酸
• 英文名称: 3-(2,4-Dichlorophenyl)-2-hydroxypropanoic acid
• CAS: 68921-92-6
• 化学式: C₉H₈Cl₂O₃
• 分子量: 235.067
• InChiKey: NBORNXKEEFIAMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(2,4-二氯苯基)乳酸 、 甲醇 在 phospho-tungstic acid 、 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 以79%的产率得到Methyl 3-(2,4-dichlorophenyl)-2-hydroxypropanoate
  参考文献：
  名称：

  Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism

  摘要：

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.104
• 作为产物：
  描述：

  3-(2,4-Dichloro-phenyl)-2-oxo-propionic acid 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以68%的产率得到3-(2,4-二氯苯基)乳酸
  参考文献：
  名称：

  Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism

  摘要：

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.104

文献信息

• Versatile Biocatalytic C(<i>sp</i>³)−H Oxyfunctionalization for the Site‐ Selective and Stereodivergent Synthesis of α‐ and β‐Hydroxy Acids
  作者：Yingle Mao、Weijie Zhang、Zunyun Fu、Yanqiong Liu、Lin Chen、Xin Lian、Dan Zhuo、Jiewei Wu、Mingyue Zheng、Cangsong Liao

  DOI：10.1002/anie.202305250

  日期：2023.8.14

  α-ketoglutarate-dependent aryloxyalkanoate dioxygenases (AADs) are repurposed for applications in biocatalytic oxyfunctionalization. Activity profiling of natural AADs enabled the synthesis of four types of α-and β-hydroxy acids with broad scope, high efficiency, and good selectivity.

  在此，α-酮戊二酸依赖性芳氧基链烷酸双加氧酶（AAD）被重新用于生物催化氧功能化中的应用。天然 AAD 的活性分析使得四种类型的α-和β-羟基酸的合成具有广泛、高效和良好的选择性。
• PROCESS FOR PRODUCING 1,2-ETHANEDIOL DERIVATIVES
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0816316A1

  公开（公告）日：1998-01-07

  A process for preparing a 1,2-ethanediol derivative in a high yield by reducing an α-hydroxy carboxylic acid ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium boron hydride compound. A process for preparing a 1,2-ethanediol derivative in a high yield by esterifying an α-hydroxy carboxylic acid derivative to synthesize an α-hydroxy carboxylic acid ester derivative, and reducing this ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium borohydride compound in the same reaction vessel.

  一种在氢化硼钠化合物存在下，通过在原生溶剂或含水非丙烯极性溶剂中还原 α-羟基羧酸酯衍生物，以高产率制备 1，2-乙二醇衍生物的工艺。一种通过酯化α-羟基羧酸衍生物合成α-羟基羧酸酯衍生物，并在同一反应容器中，在有硼氢化钠化合物存在的情况下，在质子溶剂或含水非丙烷极性溶剂中还原该酯衍生物，从而高产率制备1，2-乙二醇衍生物的工艺。