(5aS,10aS)-5a,10a-dimethyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione | 922170-11-4

• 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: (5aS,10aS)-5a,10a-dimethyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione
• 英文别名: (3S,9S)-3,9-dimethyl-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 922170-11-4
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: QGLMICHBDPPLJT-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5aS,10aS)-5a,10a-dimethyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以67%的产率得到(5aS,10aS)-5a,10a-dimethyldecahydrodipyrrolo[1,2-a:1',2'-d]pyrazine
  参考文献：
  名称：

  Design and Synthesis of Novel C₂-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols

  摘要：

  A novel alicyclic chiral C-2-symmetric piperazine, (S, S)-7, is designed and synthesized from L-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl2 provided optically active monobenzoates with high enantioselectivity.

  DOI：

  10.1021/ol0626387
• 作为产物：
  描述：

  维格列汀杂质 在 lithium diethylamide 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (5aS,10aS)-5a,10a-dimethyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione
  参考文献：
  名称：

  Design and Synthesis of Novel C₂-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols

  摘要：

  A novel alicyclic chiral C-2-symmetric piperazine, (S, S)-7, is designed and synthesized from L-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl2 provided optically active monobenzoates with high enantioselectivity.

  DOI：

  10.1021/ol0626387

文献信息

• Microwave-Assisted Stereoselective One-Pot Synthesis of Symmetrical and Unsymmetrical 2,5-Diketopiperazines from Unprotected Amino Acids
  作者：Manuel Jainta、Martin Nieger、Stefan Bräse

  DOI：10.1002/ejoc.200800605

  日期：2008.11

  The facile condensation of unprotected amino acids by a phosphite-promoted one-step coupling reaction is a highly efficient synthesis to generate stereoselective and optically pure symmetrical and unsymmetrical functionalized diketopiperazines. The use of microwaves enhanced by small amounts of ionic liquid is accompanied by significant improvement in reaction times and yields. Simple filtration through

  通过亚磷酸酯促进的一步偶联反应轻松缩合未保护的氨基酸是一种高效的合成方法，可以生成立体选择性和光学纯的对称和不对称官能化二酮哌嗪。使用由少量离子液体增强的微波伴随着反应时间和产率的显着改善。通过硅胶垫的简单过滤提供了非常好的纯化合物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）
• Design and Synthesis of Novel <i>C</i>₂-Symmetric Chiral Piperazines and an Application to Asymmetric Acylation of σ-Symmetric 1,2-Diols
  作者：Daisuke Nakamura、Kiyomi Kakiuchi、Kenji Koga、Ryuichi Shirai

  DOI：10.1021/ol0626387

  日期：2006.12.1

  A novel alicyclic chiral C-2-symmetric piperazine, (S, S)-7, is designed and synthesized from L-proline. Benzoylation of a series of cyclic and acyclic meso-1,2-diols with a catalytic amount of (S,S)-7 and CuCl2 provided optically active monobenzoates with high enantioselectivity.