(3aR,6aS)-tert-butyl 5-(pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate | 1338833-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aR,6aS)-tert-butyl 5-(pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
• 英文别名: tert-butyl (3aS,6aR)-2-pyrazin-2-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate
• CAS: 1338833-15-0
• 化学式: C₁₅H₂₂N₄O₂
• 分子量: 290.365
• InChiKey: HUDBGUDZDFISFN-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,6aS)-tert-butyl 5-(pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到(3aR,6aS)-2-(pyrazin-2-yl)octahydropyrrolo[3,4-c]pyrrole trifluoroacetate
  参考文献：
  名称：

  Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands

  摘要：

  A series of diazabicyclo[3.3.0]octane substituted pyridines and pyrazines was synthesized and characterized at the alpha 4 beta 2 neuronal nicotinic acetylcholine receptor (nAChR). The compounds were designed to mimic the profile of ABT-089, high affinity binding ligand for the alpha 4 beta 2 nAChR, with limited agonist activity. Carboxamide derivatives of 3-(diazabicyclo[3.3.0]octane)-substituted pyridines or 2-(diazabicyclo[3.3.0]octane)-substituted pyrazines were found to have the desired binding and activity profile. The structure-activity relationship of these compounds is presented.

  DOI：

  10.1021/jm201045m
• 作为产物：
  描述：

  2-氯吡嗪 、 tert-butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 21.0h， 以35%的产率得到(3aR,6aS)-tert-butyl 5-(pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
  参考文献：
  名称：

  Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands

  摘要：

  A series of diazabicyclo[3.3.0]octane substituted pyridines and pyrazines was synthesized and characterized at the alpha 4 beta 2 neuronal nicotinic acetylcholine receptor (nAChR). The compounds were designed to mimic the profile of ABT-089, high affinity binding ligand for the alpha 4 beta 2 nAChR, with limited agonist activity. Carboxamide derivatives of 3-(diazabicyclo[3.3.0]octane)-substituted pyridines or 2-(diazabicyclo[3.3.0]octane)-substituted pyrazines were found to have the desired binding and activity profile. The structure-activity relationship of these compounds is presented.

  DOI：

  10.1021/jm201045m