cis-1-benzyl-3,4-diacetoxypyrrolidin-2,5-dione | 155487-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-1-benzyl-3,4-diacetoxypyrrolidin-2,5-dione
• 英文别名: [(3S,4R)-4-acetyloxy-1-benzyl-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 155487-41-5
• 化学式: C₁₅H₁₅NO₆
• 分子量: 305.287
• InChiKey: MGGABTRPYQRCJY-BETUJISGSA-N

物化性质

• 沸点：
  485.8±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-1-benzyl-3,4-diacetoxypyrrolidin-2,5-dione 在 硼烷四氢呋喃络合物 、 (2S,3R)-2-amino-3-(t-butyldimethylsiloxy)-1,1-diphenylbutanol 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以42%的产率得到Acetic acid (2S,3R,4S)-4-acetoxy-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester
  参考文献：
  名称：

  Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin

  摘要：

  Highly enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from L-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was successfully applied to the synthesis of (+)-deoxybiotin in an enantio-controlled manner in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01864-x
• 作为产物：
  描述：

  O,O′-diacetyl meso-tartaric acid 在 乙酰氯 作用下， 反应 9.5h， 生成 cis-1-benzyl-3,4-diacetoxypyrrolidin-2,5-dione
  参考文献：
  名称：

  Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

  摘要：

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00154-7

文献信息

• Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides
  作者：Romeo Romagnoli、Eric C. Roos、Henk Hiemstra、Marinus J. Moolenaar、W. Nico Speckamp、Bernard Kaptein、Hans E. Schoemaker

  DOI：10.1016/s0040-4039(00)79972-2

  日期：1994.2

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.