(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester | 13513-80-9

• 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: (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester
• 英文别名: γ-Butyloxycarbonyl-γ-butyrolacton；Butyl 5-oxooxolane-2-carboxylate；butyl 5-oxooxolane-2-carboxylate
• CAS: 13513-80-9
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: DLDDXBBRJYTPJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester 生成 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4
• 作为产物：
  描述：

  (+/-)-di-n-butyl 2-hydroxypentandioate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以50%的产率得到(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4

文献信息

• Optically pure and enriched isomers of chelating ligands and contrast agents
  申请人：Amedio C. John

  公开号：US20070244316A1

  公开（公告）日：2007-10-18

  Organic chelating ligands, organic chelating ligand precursors, and metal chelates are disclosed. Methods for synthesizing the same are also described, including methods for preparing optically-enriched or optically-pure compositions of the same.

  本发明公开了有机螯合配体、有机螯合配体前体和金属螯合物。还描述了合成它们的方法，包括制备光学富集或光学纯的相同组成的方法。
• METHOD FOR SYNTHESIZING 2-BROMOGLUTARIC ACID DIESTERS
  申请人：GUERBET

  公开号：US20230303477A1

  公开（公告）日：2023-09-28

  The present invention relates to a process for preparing the 2-bromoglutaric acid diester of formula (I) below: comprising the formation of the 2-hydroxyglutaric acid diester of formula (II) by reaction of butyrolactone acid of formula (BA) with the alcohol of formula ROH, in the presence of an acid such as sulfuric acid; and bromination of the 2-hydroxyglutaric acid diester of formula (II), by sparging with gaseous hydrobromic acid. The present invention also relates to a 2-bromoglutaric acid diester of formula (I), having a degree of purity determined by HPLC analysis of greater than or equal to 90%.
• Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
  作者：Sara Drioli、Patrizia Nitti、Giuliana Pitacco、Laura Tossut、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00286-4

  日期：1999.7

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.