methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate | 312599-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate
• 英文别名: methyl (3S)-3-hydroxy-3-(3-methoxyphenyl)propanoate
• CAS: 312599-09-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: FNBHACUOQNHQRF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(3-甲氧基苯基)-3-氧丙酸甲酯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 potassium tert-butylate 、 氢气 、 C₃₉H₄₀N₃OP 作用下， 以 甲醇 为溶剂， 30.0 ℃ 、7.0 MPa 条件下， 以93 %的产率得到methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate
  参考文献：
  名称：

  金鸡纳生物碱衍生的 NNP 配体用于铱催化 β-酮酯的不对称氢化

  摘要：

  已经开发出 Ir 催化的 β-酮酯与金鸡纳生物碱衍生的 NNP 配体的不对称氢化反应。使用分别衍生自奎尼丁和奎宁的 NNP L2和L7 ，即使在克级，也可以顺利地获得相反构型的 β-羟基酯，分别为 91.5-99.1 和 81.6-99.3% ee。通过配体构型的简单转换来制备相反构型的β-羟基酯的方案为生物活性分子和药物的合成提供了进一步的机会。

  DOI：

  10.1021/acs.joc.3c02032

文献信息

• Ni(II)-Catalyzed Enantioselective Synthesis of β-Hydroxy Esters with Carboxylate Assistance
  作者：Na Wang、Hongxin Liu、Hang Gao、Jiafeng Zhou、Longzhangdi Zheng、Juan Li、Hong-Ping Xiao、Xinhua Li、Jun Jiang

  DOI：10.1021/acs.orglett.9b02297

  日期：2019.9.6

  decarboxylative aldol reaction between malonic acid half-oxyesters and various carbonyls with carboxylate assistance was developed, affording structurally diverse β-hydroxy esters with good yields and enantioselectivities under mild conditions. Importantly, the broad substrate scope of this methodology enabled rapid accesses to several natural products and their analogues as exemplified by phenylpropanoid, phaitanthrin

  建立了Ni-恶唑啉配合物催化丙二酸半含氧酸酯和各种羰基在羧酸酯辅助下的不对称脱羧醛醇缩合反应，在温和条件下以良好的收率和对映选择性提供了结构多样的β-羟基酯。重要的是，这种方法的广泛的底物范围使人们能够快速获得几种天然产物及其类似物，例如苯丙烷，类赤霉素B和邻苯二甲酸酯。
• Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications
  作者：Paweł Borowiecki、Maria Bretner

  DOI：10.1016/j.tetasy.2013.06.004

  日期：2013.8

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.
• Braun, Manfred; Bauer, Claus, Liebigs Annalen der Chemie, 1991, # 11, p. 1157 - 1164
  作者：Braun, Manfred、Bauer, Claus

  DOI：——

  日期：——