(E)-3-(2-pyridylmethylene)-1-azabicyclo[2.2.2]octane

• 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: (E)-3-(2-pyridylmethylene)-1-azabicyclo[2.2.2]octane
• 英文别名: (3E)-3-(pyridin-2-ylmethylidene)-1-azabicyclo[2.2.2]octane
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: MVQHXSQFWKKAOZ-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-picolyl)trimethylsilane 、 3-奎宁环酮 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 (E)-3-(2-pyridylmethylene)-1-azabicyclo[2.2.2]octane 、 (Z)-3-(2-pyridylmethylene)-1-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Bioisosteric replacement strategy for the synthesis of 1-azacyclic compounds with high affinity for the central nicotinic cholinergic receptors

  摘要：

  Bioisosteric replacement of the isoxazole heterocycle in (3-methyl-5-isoxazolyl)methylene-azacyclic compounds with pyridine, oxadiazole, or an acyl group resulted in ligands with high to moderate affinity for the central nicotinic cholinergic receptors (IC50 = 2.0 to IC50 > 1000 nM) labeled by [H-3]methylcarbamylcholine. Additionally, further support of an important distance parameter for high-affinity nicotinic compounds has been provided. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00063-8

文献信息

• Bioisosteric replacement strategy for the synthesis of 1-azacyclic compounds with high affinity for the central nicotinic cholinergic receptors
  作者：Preben H. Olesen、Janne E. Tønder、John Bondo Hansen、Holger C. Hansen、Karin Rimvall

  DOI：10.1016/s0968-0896(00)00063-8

  日期：2000.6

  Bioisosteric replacement of the isoxazole heterocycle in (3-methyl-5-isoxazolyl)methylene-azacyclic compounds with pyridine, oxadiazole, or an acyl group resulted in ligands with high to moderate affinity for the central nicotinic cholinergic receptors (IC50 = 2.0 to IC50 > 1000 nM) labeled by [H-3]methylcarbamylcholine. Additionally, further support of an important distance parameter for high-affinity nicotinic compounds has been provided. (C) 2000 Elsevier Science Ltd. All rights reserved.