3-(4-甲氧基苯基)-3-羟基丙酸甲酯 | 13305-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-甲氧基苯基)-3-羟基丙酸甲酯
• 英文名称: methyl 3-(4-methoxyphenyl)-3-hydroxypropanoate
• 英文别名: Methyl 3-hydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 13305-16-3
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: SLSMILXGFSQOHY-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±32.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

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

安全信息

• 储存条件：
  存于室温下，密封保存，并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯基)-3-羟基丙酸甲酯 在 碘 、 lithium diisopropyl amide 作用下， 生成 (2R,3S)-rel-3-(4-甲氧基苯基)-2-环氧乙烷羧酸甲酯
  参考文献：
  名称：

  Asymmetric Reduction of Aromatic Ketones. II. An Enantioselective Synthesis of Methyl(2R,3S)-3-(4-Methoxypehnyl)glycidate.

  摘要：

  研究了某些3-酮酯（6、8和11）通过不同手性还原剂不对称还原为3-羟基酯（7、9和12）的过程。产物（9和12）被转化为甲基（2R, 3S）-3-（4-甲氧基苯基）缩水甘油酸酯（2R, 3S-3），这是在实际合成Diltiazem（1）的对映选择性合成中的关键中间体。

  DOI：

  10.1248/cpb.41.643
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-3-氧代丙酸甲酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以91%的产率得到3-(4-甲氧基苯基)-3-羟基丙酸甲酯
  参考文献：
  名称：

  Asymmetric Reduction of Aromatic Ketones. II. An Enantioselective Synthesis of Methyl(2R,3S)-3-(4-Methoxypehnyl)glycidate.

  摘要：

  研究了某些3-酮酯（6、8和11）通过不同手性还原剂不对称还原为3-羟基酯（7、9和12）的过程。产物（9和12）被转化为甲基（2R, 3S）-3-（4-甲氧基苯基）缩水甘油酸酯（2R, 3S-3），这是在实际合成Diltiazem（1）的对映选择性合成中的关键中间体。

  DOI：

  10.1248/cpb.41.643

文献信息

• 부테놀라이드계 화합물과 그의 제조방법 및 그를 포함하는 약제학적 조성물
  申请人：Seoul National University R&DB Foundation 서울대학교산학협력단(120070509242) Corp. No ▼ 114371-0009224BRN ▼119-82-03684

  公开号：KR101599426B1

  公开（公告）日：2016-03-07

  본 발명은 부테놀라이드계 화합물, 그의 입체이성질체, 그의 거울상이성질체, 생체 내에서 가수분해 가능한 그의 전구체 또는 약제학적으로 허용 가능한 그의 염 및 그들이 갖는 항균활성, 면역질환치료 및 예방 활성, 암의 예방 또는 치료 효능 및 의료용 삽입기기의 오손 방지 활성에 관한 것이다.

  This text is already in Korean. Would you like a translation into another language?
• [EN] METHOD OF PREPARATION OF OPTICALLY ACTIVE ALCOHOLS<br/>[FR] PROCEDE D'ELABORATION D'ALCOOLS OPTIQUEMENT ACTIFS
  申请人：POSTECH FOUNDATION

  公开号：WO2005009935A1

  公开（公告）日：2005-02-03

  The present invention relates to a method for preparing chiral alcohol having optical activity. More specifically, the present invention relates to a method for preparing (S)-chiral alcohol with a high yield and a high optical purity by mixing achiral substrates such as racemic alcohol or ketone with metal catalyst and protein hydrolase to perform a dynamic kinetic resolution reaction.

  本发明涉及一种制备具有光学活性的手性醇的方法。更具体地说，本发明涉及一种通过将非手性底物（如消旋醇或酮）与金属催化剂和蛋白水解酶混合，进行动力学分辨反应，从而高产率、高光学纯度地制备(S)-手性醇的方法。
• 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.
• A one-pot silyl-Reformatsky olefination
  作者：James M. Smith、Michael F. Greaney

  DOI：10.1016/j.tetlet.2007.10.029

  日期：2007.12

  A novel one-pot olefination reaction has been developed, involving the stereoselective formation of (E)-alpha,beta-unsaturated esters/ketones from the reaction of alpha-bromocarbonyl compounds with aromatic aldehydes. The reactions use a reagent combination of trichlorosilane, and triethylamine and may proceed via the in situ formation of a trichlorosilyl ketene acetal. The general procedure offers key advantages (high conversions, low quantities of organic soluble by-products) over the conventional Wittig reaction. (C) 2007 Elsevier Ltd. All rights reserved.
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.