2-[2-(3-Fluorophenyl)ethyl]-2-azatricyclo[3.3.1.13,7]decane;hydrochloride | 1333413-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-(3-Fluorophenyl)ethyl]-2-azatricyclo[3.3.1.13,7]decane;hydrochloride
• CAS: 1333413-88-9
• 化学式: C₁₇H₂₂FN*ClH
• 分子量: 295.828
• InChiKey: MHCCJSGASQACQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  3.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二环[3.3.1]壬-3,7-二酮 在 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 37.17h， 生成 2-[2-(3-Fluorophenyl)ethyl]-2-azatricyclo[3.3.1.13,7]decane;hydrochloride
  参考文献：
  名称：

  N-Arylalkyl-2-azaadamantanes as cage-expanded polycarbocyclic sigma (σ) receptor ligands

  摘要：

  A series of racemic N-arylalkyl-2-azaadamantan-1-ols (9-15) and the corresponding deoxygenated, achiral N-arylalkyl-2-azaadamantanes (23-29) were synthesized and screened in competition binding assays against a panel of CNS targets. Adamantyl hemiaminals 9-15 displayed generally low affinity for both sigma(1) (K-i values = 294-1950 nM) and sigma(2) receptors (K-i values = 201-1020 nM), and negligible affinity for 42 other CNS proteins. Deoxygenation of 9-15 to give the corresponding achiral azaadamantanes 23-29 greatly improved affinity for sigma(1) (K-i values = 8.3-239 nM) and sigma(2) receptors (K-i values = 34-312 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.028

文献信息

• N-Arylalkyl-2-azaadamantanes as cage-expanded polycarbocyclic sigma (σ) receptor ligands
  作者：Samuel D. Banister、David T. Yoo、Sook Wern Chua、Jinquan Cui、Robert H. Mach、Michael Kassiou

  DOI：10.1016/j.bmcl.2011.07.028

  日期：2011.9

  A series of racemic N-arylalkyl-2-azaadamantan-1-ols (9-15) and the corresponding deoxygenated, achiral N-arylalkyl-2-azaadamantanes (23-29) were synthesized and screened in competition binding assays against a panel of CNS targets. Adamantyl hemiaminals 9-15 displayed generally low affinity for both sigma(1) (K-i values = 294-1950 nM) and sigma(2) receptors (K-i values = 201-1020 nM), and negligible affinity for 42 other CNS proteins. Deoxygenation of 9-15 to give the corresponding achiral azaadamantanes 23-29 greatly improved affinity for sigma(1) (K-i values = 8.3-239 nM) and sigma(2) receptors (K-i values = 34-312 nM). (C) 2011 Elsevier Ltd. All rights reserved.