di-i-butyl 2-oxo-pentandioate | 77630-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: di-i-butyl 2-oxo-pentandioate
• 英文别名: di-n-butyl 2-oxoglutarate；2-Oxo-glutarsaeure-dibutylester；Dibutyl 2-oxopentanedioate
• CAS: 77630-52-5
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: SDYKGJKTLYBKEN-UHFFFAOYSA-N

物化性质

• 沸点：
  140-141.5 °C(Press: 3 Torr)
• 密度：
  1.026 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-i-butyl 2-oxo-pentandioate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 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：

  alpha-酮戊二酸 、 正丁醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以90%的产率得到di-i-butyl 2-oxo-pentandioate
  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

• METHOD FOR PURIFYING PYRUVIC ACID COMPOUNDS
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0937703A1

  公开（公告）日：1999-08-25

  The present invention is directed to a method for purifying pyruvic acid compounds, which method comprises reacting a pyruvic acid compound of general formula (I): wherein R1 is an optionally substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and R2 is a lower alkyl group, with a bisulfite of general formula (II):         MHSO3     (II) wherein M is NH4 or an alkali metal, to give a bisulfite adduct of the pyruvic acid compound and then decomposing the adduct with an acid. According to the present invention, pyruvic acid compounds can be purified by simple and easy procedures without using purification techniques such as distillation or column chromatography, and the above method is advantageous as a process for the production on an industrial scale.

  本发明涉及一种纯化丙酮酸化合物的方法，该方法包括使通式(I)的丙酮酸化合物反应： 其中 R1 是任选取代的低级烷基、低级烯基、低级炔基、环烷基、芳基或杂环基，R2 是低级烷基，与通式（II）的亚硫酸氢盐反应： MHSO3 (II) 其中 M 为 NH4 或碱金属，以得到丙酮酸化合物的亚硫酸氢盐加合物，然后用酸分解该加合物。根据本发明，丙酮酸化合物可以通过简单易行的程序进行纯化，而无需使用蒸馏或柱层析等纯化技术，上述方法作为一种工业规模的生产工艺是非常有利的。
• Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
  作者：Eduardo M. Rustoy、Elba N. Pereyra、Silvia Moreno、Alicia Baldessari

  DOI：10.1016/j.tetasy.2004.10.013

  日期：2004.11

  An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantionterically pure 3-carboxyalkyl-gamma-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-gamma-butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells. (C) 2004 Elsevier Ltd. All rights reserved.
• PREVENTION OF THE OXIDATION OF PERFUMERY RAW MATERIALS AND FOOD RAW MATERIALS
  申请人：Firmenich SA

  公开号：US20210395638A1

  公开（公告）日：2021-12-23

  The various aspects presented herein relate to methods for the reduction, prevention and/or inhibition of the oxidation of perfume ingredients, formulated perfumes, formulated body care products, formulated skin care products, formulated homecare products, essential oils, food raw materials, formulated food products and natural extracts.
• US6348617B1
  申请人：——

  公开号：US6348617B1

  公开（公告）日：2002-02-19
• 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.