methyl 8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-4-carboxylate | 50370-54-2

• 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 8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-4-carboxylate
• 英文别名: [1R-(2-endo,3-exo)]-8-Methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester；Win 35065-3；methyl (1S,3S,4S,5R)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-4-carboxylate；3β-phenyltropane-2α-carboxylic acid methyl ester
• CAS: 50370-54-2；50372-80-0；50583-05-6；57458-42-1；74163-83-0；74163-84-1；127379-25-3；127379-26-4
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: OMBOXYLBBHNWHL-APIJFGDWSA-N

物化性质

• 熔点：
  63-65oC
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  phenylmagnesium bromide 、 anhydroecgonine methyl ester 以 乙醚 为溶剂， 反应 2.5h， 以31%的产率得到methyl 8-methyl-3-phenyl-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

文献信息

• Synthesis, ligand binding, QSAR, and CoMFA study of 3.beta.-(p-substituted phenyl)tropane-2.beta.-carboxylic acid methyl esters
  作者：F. Ivy Carroll、Yigong Gao、M. Abdur Rahman、Philip Abraham、Karol Parham、Anita H. Lewin、John W. Boja、Michael J. Kuhar

  DOI：10.1021/jm00113a008

  日期：1991.9

  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.