1-(3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-azabicyclo[3.2.1]octan-8-yl)-2-hydroxy-2-phenylethanone | 1360460-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 1-(3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-azabicyclo[3.2.1]octan-8-yl)-2-hydroxy-2-phenylethanone
• CAS: 1360460-67-8
• 化学式: C₃₀H₃₁NO₃
• 分子量: 453.581
• InChiKey: JSLMZEKOJZICBH-BKWJHWGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-azabicyclo[3.2.1]octan-8-yl)-2-hydroxy-2-phenylethanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到2-(3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylethanol
  参考文献：
  名称：

  Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein

  摘要：

  Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the alpha 7 and alpha 4 beta 2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.008
• 作为产物：
  描述：

  3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane 在 potassium permanganate 、 O-(benzotriazol-1-yl )-N,N,N' ,N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 potassium hydroxide 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 1-(3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8-azabicyclo[3.2.1]octan-8-yl)-2-hydroxy-2-phenylethanone
  参考文献：
  名称：

  Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein

  摘要：

  Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the alpha 7 and alpha 4 beta 2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.008