3-(3-hydroxy-2-oxotetrahydrofuran-3-yl)propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(3-hydroxy-2-oxotetrahydrofuran-3-yl)propanoic acid
• 英文别名: 3-(3-Hydroxy-2-oxooxolan-3-yl)propanoic acid
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: PEWORQGNDNZBHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 、 2-羟基-3-(2-羟基乙基)环戊-2-烯-1-酮 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 以48%的产率得到3-(3-hydroxy-2-oxotetrahydrofuran-3-yl)propanoic acid
  参考文献：
  名称：

  Asymmetric oxidation of 1,2-cyclopentanediones

  摘要：

  Cyclic 3-alkyl-1,2-cyclopentanediones undergo a direct asymmetric oxidation with the DET/Ti(OiPr)(4)/tBuOOH oxidative system, resulting in enantiomeric alpha-hydroxy compounds and ring-cleaved hydroxylated acids (lactones) up to 95% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01106-0

文献信息

• ESTERS OF (2-HYDROXY-3-OXO-CYCLOPENT-1-ENYL) ACETIC ACID AND THEIR USE FOR PREPARING (-)-R-HOMOCITRIC ACID GAMMA-LACTONE, (+)-S-HOMOCITRIC ACID GAMMA-LACTONE AND THE CORRESPONDING (-)-R-HOMOCITRIC ACID AND (+)-S-HOMOCITRIC ACID SALTS
  申请人：Lopp Margus

  公开号：US20090187041A1

  公开（公告）日：2009-07-23

  Archiral (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid) alkyl, alkylphenyl and phenyl esters, and a simple and efficient method for the synthesis of both enantiomers of homocitric acid gamma-lactone and the corresponding salts from these esters are described. The method is based on asymmetric oxidation of esters, and the steps of basic and acidic hydrolysis and final acidic lactonization of the homocitric acid into homocitric acid gamma-lactone. The homocitric acid salts are obtained after basic treatment of homocitric acid gamma-lactone. The esters, conditions and reagents used in chemical conversion and separating products are important constituents affording efficient and simple method for production of homocitric acid gamma-lactone and homocitric acid salts.
• US8148568B2
  申请人：——

  公开号：US8148568B2

  公开（公告）日：2012-04-03
• [EN] ESTERS OF (2-HYDROXY-3-OXO-CYCLOPENT-1-ENYL) ACETIC ACID AND THEIR USE FOR PREPARING (-)-R-HOMOCITRIC ACID GAMMA-LACTONE, (+)-S-HOMOCITRIC ACID GAMMA-LACTONE AND THE CORRESPONDING (-)-R-HOMOCITRIC ACID AND (+)-S-HOMOCITRIC ACID SALTS<br/>[FR] ESTERS DE L'ACIDE (2-HYDROXY-3-OXO-CYCLOPENT-1-ÉNYL)ACÉTIQUE ET LEUR UTILISATION POUR PRÉPARER UNE GAMMA-LACTONE D'ACIDE (-)-R-HOMOCITRIQUE, UNE GAMMA-LACTONE D'ACIDE (+)-S-HOMOCITRIQUE ET LES SELS D'ACIDE (-)-R-HOMOCITRIQUE ET D'ACIDE (+)-S-HOMOCITR
  申请人：TALLINN UNIVERSITY OF TECHNOLO

  公开号：WO2007137593A1

  公开（公告）日：2007-12-06

  [EN] Archiral (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid) alkyl, alkylphenyl and phenyl esters, and a simple and efficient method for the synthesis of both enantiomers of homocitric acid gamma-lactone and the corresponding salts from these esters are described. The method is based on asymmetric oxidation of esters, and the steps of basic and acidic hydrolysis and final acidic lactonization of the homocitric acid into homocitric acid gamma-lactone. The homocitric acid salts are obtained after basic treatment of homocitric acid gamma-lactone. The esters, conditions and reagents used in chemical conversion and separating products are important constituents affording efficient and simple method for production of homocitric acid gamma-lactone and homocitric acid salts.
  [FR] L'invention concerne les esters alkylique, alkylphénylique et phénylique de l'acide (2-hydroxy-3-oxo-cyclopent-1-ényl) acétique achiraux, et un procédé simple et efficace pour la synthèse des deux énantiomères de la gamma-lactone d'acide homocitrique et les sels correspondants provenant des ces esters. Le procédé se fonde sur une oxydation asymétrique des esters, et sur les étapes d'hydrolyse basique et acide, et de lactonisation acide finale de l'acide homocitrique en gamma-lactone d'acide homocitrique. Les sels d'acide homocitrique sont obtenus après un traitement basique de la gamma-lactone d'acide homocitrique. Les esters, conditions et réactifs utilisés en conversion chimique et pour la séparation de produits, sont des constituants importants fournissant un procédé simple et efficace pour la production de gamma-lactone d'acide homocitrique et de sels d'acide homocitrique.