8-azabicyclo[3.2.1]octan-3-yl benzoate,hydrochloride | 17366-47-1

• 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: 8-azabicyclo[3.2.1]octan-3-yl benzoate,hydrochloride
• 英文别名: 3α-benzoyloxy-8-azabicyclo[3.2.1]octane hydrochloride；3β-benzoyloxynortropane hydrochloride；3exo-benzoyloxy-nortropane; hydrochloride；3exo-Benzoyloxy-nortropan; Hydrochlorid
• CAS: 17366-47-1；76678-93-8
• 化学式: C₁₄H₁₇NO₂*ClH
• 分子量: 267.755
• InChiKey: UTZOTWHWGTZKTK-NOGCFKFUSA-N

物化性质

• 熔点：
  235-240 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-azabicyclo[3.2.1]octan-3-yl benzoate,hydrochloride 在 硼烷四氢呋喃络合物 、 O-(benzotriazol-1-yl )-N,N,N' ,N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 3α-(benzoyloxy)-8-(2-hydroxy-2-phenylethyl)-azabicyclo[3.2.1]octane methiodide
  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：

  pseudotropine 在 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 10.0h， 生成 8-azabicyclo[3.2.1]octan-3-yl benzoate,hydrochloride
  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

文献信息

• Configuration of Tropine and Pseudotropine
  作者：Alex Nickon、Louis F. Fieser

  DOI：10.1021/ja01142a005

  日期：1952.11
• 150. The stereochemistry of the tropane alkaloids. Part I. The configuration of tropine and ψ-tropine
  作者：Gábor Fodor、Károly Nádor

  DOI：10.1039/jr9530000721

  日期：——