1-azabicyclo<2.2.2>octan-3-one O-methyloxime

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 1-azabicyclo<2.2.2>octan-3-one O-methyloxime
• 英文别名: (Z)-N-methoxy-1-azabicyclo[2.2.2]octan-3-imine
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: LGUSLYYEVXTENW-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azabicyclo<2.2.2>octan-3-one O-methyloxime 在 盐酸 、 三乙胺-硼烷 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-O-methyl-hydroxylamine
  参考文献：
  名称：

  Synthesis and muscarinic M3 pharmacological activities of 1-azabicyclo[2.2.2]octan-3-one oxime derivatives

  摘要：

  A series of 1-azabicyclo[2.2.2]octan-3-one oximes and related 1-azabicyclo-[2.2.2]-octan-3-one hydroxylamines were synthesized and tested for muscarinic M(3) activity. All compounds showed at least some muscarinic binding properties, however, only one member of the series demonstrated mucarinic M(3) agonistic properties in vitro (contraction of guinea pig ileum) and in vivo (mydriasis, salivation). In addition, this compound partially reversed the cognitive deficit induced by central cholinergic depletion in two procedures testing memory in the rat, namely the delayed matching to position and swim maze tasks of spatial memory in the rat.

  DOI：

  10.1016/0968-0896(96)00035-1
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 3-奎宁环酮盐酸盐 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到1-azabicyclo<2.2.2>octan-3-one O-methyloxime
  参考文献：
  名称：

  Synthesis and muscarinic M3 pharmacological activities of 1-azabicyclo[2.2.2]octan-3-one oxime derivatives

  摘要：

  A series of 1-azabicyclo[2.2.2]octan-3-one oximes and related 1-azabicyclo-[2.2.2]-octan-3-one hydroxylamines were synthesized and tested for muscarinic M(3) activity. All compounds showed at least some muscarinic binding properties, however, only one member of the series demonstrated mucarinic M(3) agonistic properties in vitro (contraction of guinea pig ileum) and in vivo (mydriasis, salivation). In addition, this compound partially reversed the cognitive deficit induced by central cholinergic depletion in two procedures testing memory in the rat, namely the delayed matching to position and swim maze tasks of spatial memory in the rat.

  DOI：

  10.1016/0968-0896(96)00035-1

文献信息

• Azabicyclo and azacyclo oxime and amine cholinergic agents and pharmaceutically acceptable salts thereof
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0445731B1

  公开（公告）日：1996-01-10
• Synthesis and muscarinic M3 pharmacological activities of 1-azabicyclo[2.2.2]octan-3-one oxime derivatives
  作者：Ralf Plate、Marc J.M. Plaum、Thijs de Boer、John S. Andrews

  DOI：10.1016/0968-0896(96)00035-1

  日期：1996.2

  A series of 1-azabicyclo[2.2.2]octan-3-one oximes and related 1-azabicyclo-[2.2.2]-octan-3-one hydroxylamines were synthesized and tested for muscarinic M(3) activity. All compounds showed at least some muscarinic binding properties, however, only one member of the series demonstrated mucarinic M(3) agonistic properties in vitro (contraction of guinea pig ileum) and in vivo (mydriasis, salivation). In addition, this compound partially reversed the cognitive deficit induced by central cholinergic depletion in two procedures testing memory in the rat, namely the delayed matching to position and swim maze tasks of spatial memory in the rat.