(5aS,10aS)-5a-methyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione | 454693-95-9

• 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-methyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione
• 英文别名: (3S,9S)-3-methyl-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 454693-95-9
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: SRHGEORVVWANIY-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 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-methyloctahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione 在 lithium aluminium tetrahydride 、 lithium diethylamide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 (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 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 以65%的产率得到(5aS,10aS)-5a-methyloctahydrodipyrrolo[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

• Highly Diastereoselective Desymmetrizations of Cyclo(Pro,Pro):  An Enantioselective Strategy toward Phakellstatin and Phakellin
  作者：Karine G. Poullennec、Anna T. Kelly、Daniel Romo

  DOI：10.1021/ol026140q

  日期：2002.8.1

  [GRAPHICS]Monoenolates of C-2-symmetric, proline-derived piperazine-2,5-diones were generated and trapped with a variety of electrophiles to produce, in a highly diastereoselective fashion, functionalized diketopiperazines (DKPs). These reactions provide the basis for an asymmetric, desymmetrization strategy toward the marine alkaloids phakellstatin and phakellin, The relative stereochemistry of the functionalized DKPs was confirmed by single-crystal X-ray analysis and/or NOE experiments. Bis-functionalization of the DKPs was also found to proceed with high levels of diastereoselectivity.
• 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.