(+/-)-di-n-butyl 2-hydroxypentandioate | 92156-01-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-di-n-butyl 2-hydroxypentandioate
• 英文别名: butyl 2-hydroxyglutarate；2-Hydroxy-glutarsaeure-dibutylester；Dibutyl 2-hydroxypentanedioate；dibutyl 2-hydroxypentanedioate
• CAS: 92156-01-9
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: NNOJRRIHWYRKSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alpha-酮戊二酸 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (+/-)-di-n-butyl 2-hydroxypentandioate
  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

• [EN] METHOD FOR SYNTHESISING 2-BROMOGLUTARIC ACID DIESTERS<br/>[FR] PROCEDE DE SYNTHESE DE DIESTERS D'ACIDE 2-BROMOGLUTARIQUE
  申请人：GUERBET SA

  公开号：WO2022013440A1

  公开（公告）日：2022-01-20

  La présente invention a trait à un procédé de préparation du diester d'acide 2-bromoglutarique de formule (I) comprenant la du formation du diester d'acide 2-hydroxyglutarique de formule (II) par réaction de l'acide butyrolactone de formule (BA) avec l'alcool de formule ROH, en présence d'un acide tel que l'acide sulfurique; et la bromation du diester d'acide 2-hydroxyglutarique de formule (II), par bullage d'acide bromhydrique gazeux. La présente invention concerne en outre un diester d'acide 2-bromoglutarique de formule (I), ayant un degré de pureté déterminé par analyse HPLC, supérieur ou égal à 90 %.
• 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.