methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate | 127279-73-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate
• 英文别名: methyl (1S,3S,4S,5R)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]octane-4-carboxylate；3β-(4-nitrophenyl)tropane-2β-carboxylic acid methyl ester
• CAS: 127279-73-6；127379-27-5
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: JWBRJGZNZCKAEB-KBXIAJHMSA-N

物化性质

• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate 在 Ra-Ni 氢气 作用下， 以 甲醇 为溶剂， 以77%的产率得到methyl 3-(4-aminophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
  参考文献：
  名称：

  Synthesis, ligand binding, QSAR, and CoMFA study of 3.beta.-(p-substituted phenyl)tropane-2.beta.-carboxylic acid methyl esters

  摘要：

  A series of 3-beta-(p-substituted phenyl)tropane-2-beta-carboxylic acid methyl esters (2) were synthesized and found to possess high affinity for the cocaine binding site in rat striatum. The p-chloro (2c) and p-iodo (2n) compounds, which were the most potent analogues prepared, were found to be 85 and 78 times more potent than (-)-cocaine. The p-bromo (2m) and p-methyl (2d) were also 56 and 60 times more potent than cocaine. QSAR and CoMFA studies were conducted to correlate binding affinity of the cocaine analogues with their structural features. Whereas the QSAR study gave relatively low correlations, the CoMFA study gave a correlation with high predictive value.

  DOI：

  10.1021/jm00113a008
• 作为产物：
  描述：

  phenylmagnesium bromide 在 nitronium tetrafluoborate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate
  参考文献：
  名称：

  Synthesis, ligand binding, QSAR, and CoMFA study of 3.beta.-(p-substituted phenyl)tropane-2.beta.-carboxylic acid methyl esters

  摘要：

  A series of 3-beta-(p-substituted phenyl)tropane-2-beta-carboxylic acid methyl esters (2) were synthesized and found to possess high affinity for the cocaine binding site in rat striatum. The p-chloro (2c) and p-iodo (2n) compounds, which were the most potent analogues prepared, were found to be 85 and 78 times more potent than (-)-cocaine. The p-bromo (2m) and p-methyl (2d) were also 56 and 60 times more potent than cocaine. QSAR and CoMFA studies were conducted to correlate binding affinity of the cocaine analogues with their structural features. Whereas the QSAR study gave relatively low correlations, the CoMFA study gave a correlation with high predictive value.

  DOI：

  10.1021/jm00113a008