(+/-)-di-i-propyl 2-hydroxypentandioate | 78267-00-2

• 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-i-propyl 2-hydroxypentandioate
• 英文别名: hydroxy-2 glutarate de diisopropyle；diisopropyl 2-hydroxyglutarate；Diisopropyl 2-hydroxypentanedioate；dipropan-2-yl 2-hydroxypentanedioate
• CAS: 78267-00-2
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: CWYDDJGBLWHAFY-UHFFFAOYSA-N

物化性质

• 沸点：
  312.3±27.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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-i-propyl 2-hydroxypentandioate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl 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 cesium fluoride 三乙氧基硅烷 作用下， 反应 0.5h， 生成 (+/-)-di-i-propyl 2-hydroxypentandioate
  参考文献：
  名称：

  还原选择性地由羰基组成的催化异质表面

  摘要：

  用乙氧基氢硅烷和碱金属氟化物作为催化剂而没有溶剂进行的羰基化合物的还原是高度选择性的。反应顺序为醛>酮>酯。在酮存在下，醛的还原是可能的，在酯存在下，酮的还原是可能的。酮酯中的酮基可以被选择性地还原。该系统的高选择性归因于三个因素：氢硅烷反应性（EtO）2 SiMeH <（EtO）3 SiH），盐的性质（KF

  DOI：

  10.1016/s0040-4020(01)97975-x

文献信息

• Selective reduction of carbonyl compounds by heterogeneous catalysis on salt surfaces
  作者：Jacqueline Boyer、Robert J. P. Corriu、Robert Perz、Catherine Réyé

  DOI：10.1039/c39810000121

  日期：——

  (EtO)3SiH and Me(EtO)2SiH activated by KF and CsF are efficient and selective agents for the heterogeneous reduction of carbonyl groups.

  由KF和CsF活化的（EtO）3 SiH和Me（EtO）2 SiH是有效的选择剂，用于羰基的异质还原。
• Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
  作者：Valéria Riatto、Mauricio Victor、Jaqueline Sousa、Carla Menegola

  DOI：10.21577/0103-5053.20180165

  日期：——

  To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral alpha-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose. the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
• BOYER J.; CORRIU R. J. P.; PERZ R.; REYE C., TETRAHEDRON, 1981, 37, NO 11, 2165-2171
  作者：BOYER J.、 CORRIU R. J. P.、 PERZ R.、 REYE C.

  DOI：——

  日期：——
• Reduction selective de composes carbonyles par catalyse heterogene a la surface des sels
  作者：J. Boyer、R.J.P. Corriu、R. Perz、C. Reye

  DOI：10.1016/s0040-4020(01)97975-x

  日期：1981.1

  The reduction of carbonyl compounds carried out with ethoxyhydrogenosilanes and alkali metal fluorides as catalyst and without solvent is highly selective. The reactivity order is aldehyde > ketone > ester. The reduction of aldehydes is possible in the presence of ketones, and of ketones in the presence of esters. The keto-group in a keto-ester can be selectively reduced. The high selectivity of this

  用乙氧基氢硅烷和碱金属氟化物作为催化剂而没有溶剂进行的羰基化合物的还原是高度选择性的。反应顺序为醛>酮>酯。在酮存在下，醛的还原是可能的，在酯存在下，酮的还原是可能的。酮酯中的酮基可以被选择性地还原。该系统的高选择性归因于三个因素：氢硅烷反应性（EtO）2 SiMeH <（EtO）3 SiH），盐的性质（KF
• 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.