methyl 3-(4-chlorophenyl)-2-hydroxypropanoate | 59604-05-6

• 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: methyl 3-(4-chlorophenyl)-2-hydroxypropanoate
• CAS: 59604-05-6
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: WDSQDRADSGGACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-chlorophenyl)-2-hydroxypropanoate 在 甲醇 、 水 、 sodium hydroxide 作用下， 以811 mg的产率得到3-(4-chlorophenyl)-2-hydroxypropanoic acid
  参考文献：
  名称：

  用于 α- 和 β- 羟基酸位点选择性和立体发散合成的多功能生物催化 C(sp3)−H 氧官能化

  摘要：

  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。

  DOI：

  10.1002/anie.202305250
• 作为产物：
  描述：

  3-(4-氯苯基)-2-羟基-丙烯酸 在 sodium hydroxide 、 sodium tetrahydroborate 、 phospho-tungstic acid 、 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 生成 methyl 3-(4-chlorophenyl)-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

文献信息

• Anomalous fluorinations of 3-aryl-2-hydroxypropanoic esters by diethylaminosulfur trifluoride (DAST)
  作者：David Haigh、Lee J. Jefcott、Katherine Magee、Hamish McNab

  DOI：10.1039/p19960002895

  日期：——

  Treatment of 3-aryl-2-hydroxypropanoic esters 8 with diethylaminosulfur trifluoride (DAST) gives considerable amounts of rearranged 2-aryl-3-fluoropropanoic esters 12 together with the expected products 11. The extent of rearrangement is dependent on solvent and on the substitution pattern of the aryl ring; the mechanism of rearrangement probably involves anchimeric assistance by the aryl group in

  用三氟化二乙基氨基硫（DAST）处理3-芳基-2-羟基丙酸酯8会产生大量的重排2-芳基-3-氟丙酸酯12和预期的产物11。重排的程度取决于溶剂和取代基芳基环的样式；重排的机制可能涉及通过反应路径的S N 1组分中的芳基进行的嵌合辅助。异构的3-羟基-2-苯基丙酸酯13的配方在相似条件下显示出少得多的重排，并且还获得了消除产物21。
• Manganese(IV)‐Mediated Hydroperoxyarylation of Alkenes with Aryl Hydrazines and Dioxygen from Air
  作者：Stephanie Kindt、Hannelore Jasch、Markus R. Heinrich

  DOI：10.1002/chem.201400064

  日期：2014.5.19

  version of the Meerwein arylation in which the introduction of oxygen is achieved by using dioxygen from the air. In this way, hydroperoxides were obtained from activated as well as non‐activated alkenes by oxidizing aryl hydrazines with manganese dioxide. The best results were obtained with α‐substituted acrylates. Importantly, the aryl hydrazine has to be added slowly to the reaction mixture to allow

  我们报告了Meerwein芳基化的新的碳氧加合类型，其中氧气的引入是通过使用空气中的双氧来实现的。通过这种方式，通过用二氧化锰氧化芳基肼，从活化的和未活化的烯烃中获得了氢过氧化物。用α-取代的丙烯酸酯可获得最佳结果。重要的是，必须将芳基肼缓慢加入反应混合物中，以使空气中的双氧充分吸收。竞争和标记实验表明氢过氧自由基是新型的以氧为中心的自由基清除剂。
• Manganese-Promoted Regioselective Ring-Opening of 2,3-Epoxy Acid Derivatives: A New Route to α-Hydroxy Acid Derivatives
  作者：José M. Concellón、Pablo L. Bernad、Humberto Rodríguez-Solla、Pamela Díaz

  DOI：10.1002/adsc.200900257

  日期：2009.9

  amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.

  描述了一种简单而通用的方法，该方法涉及由活性锰促进的从容易获得的2，3-环氧酰胺或酯合成3-芳基-2-羟基酰胺或具有总区域选择性的酯。利用对映纯的环氧酰胺作为起始原料，也可获得对映纯的相应的3-芳基-2-羟基酰胺。显示了3-芳基-2-羟基羧酸衍生物的选定实例的一些合成应用。已经提出了一种机制来解释这种新颖的反应。
• [EN] METHODS FOR PRODUCTION OF PF1022A DERIVATIVES<br/>[FR] PROCÉDÉS DE PRODUCTION DE DÉRIVÉS DE PF1022A
  申请人：ACIDOPHIL LTD

  公开号：WO2018166899A1

  公开（公告）日：2018-09-20

  Provided are processes for the production of PF1022A derivative compounds, including incubating a microorganism strain capable of producing such compounds in a culture medium to produce a resulting culture, said culture medium containing carbon and nitrogen sources, and further providing to said culture medium a feedstock comprising a compound of Formula II, Formula III, Formula IV or Formula V: (II), (III), (IV), (V) thereby producing said PF1022A derivative compound in the resulting culture. Compounds of Formula II, Formula III, Formula IV, or Formula V useful in such a feedstock are also provided.

  提供了生产PF1022A衍生物化合物的过程，包括在培养基中孵育能够产生这种化合物的微生物菌株，以产生结果培养物，所述培养基含有碳和氮源，并进一步向所述培养基提供公式II、公式III、公式IV或公式V的化合物作为原料，从而在结果培养物中产生所述PF1022A衍生物化合物。还提供了在这种原料中有用的公式II、公式III、公式IV或公式V的化合物。
• Asymmetric transfer hydrogenation of α-azido acrylates
  作者：Yang Ji、Ping Xue、Dan-Dan Ma、Xue-Qiang Li、Peiming Gu、Rui Li

  DOI：10.1016/j.tetlet.2014.11.072

  日期：2015.1

  The asymmetric transfer hydrogenation of alpha-azido acrylates has been explored, a range of alpha-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A. (C) 2014 Elsevier Ltd. All rights reserved.