5a-hydroperoxy-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazine-5,10-dione | 59685-08-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5a-hydroperoxy-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazine-5,10-dione
• 英文别名: cis-Cyclo(α-Hydroperoxy-L-Pro-L-Pro)；(3R,9S)-3-hydroperoxy-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 59685-08-4
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: DAVXPBMFRGROTN-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  维格列汀杂质 在 二苯甲酮 、 氧气 作用下， 以 乙酸乙酯 为溶剂， 反应 168.0h， 以39%的产率得到5a-hydroperoxy-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazine-5,10-dione
  参考文献：
  名称：

  Diketopiperazine-derived hydroperoxide for chemoselective oxidations of sulfides and enantioselective Weitz–Scheffer epoxidations

  摘要：

  L-Proline-derived hydroperoxide (-)-2, which was obtained from the corresponding diketopiperazine by irradiation under oxygen atmosphere, was applied to the oxidation of a variety of sulfides and asymmetric Weitz-Scheffer epoxidations of cyclic and acyclic enones. The sulfoxidation, however, gave only racemic products. In contrast, depending on the base catalyst, enantio selectivities up to 37% were achieved in the epoxidation of chalcone with (-)-2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.090

文献信息

• Diketopiperazine-derived hydroperoxide for chemoselective oxidations of sulfides and enantioselective Weitz–Scheffer epoxidations
  作者：Marcel Kienle、Wassiliki Argyrakis、Angelika Baro、Sabine Laschat

  DOI：10.1016/j.tetlet.2008.01.090

  日期：2008.3

  L-Proline-derived hydroperoxide (-)-2, which was obtained from the corresponding diketopiperazine by irradiation under oxygen atmosphere, was applied to the oxidation of a variety of sulfides and asymmetric Weitz-Scheffer epoxidations of cyclic and acyclic enones. The sulfoxidation, however, gave only racemic products. In contrast, depending on the base catalyst, enantio selectivities up to 37% were achieved in the epoxidation of chalcone with (-)-2. (c) 2008 Elsevier Ltd. All rights reserved.