dimethyl 3-bromo-7-azabicyclo[2.2.1]hept-2-ene-2,7-dicarboxylate | 208177-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: dimethyl 3-bromo-7-azabicyclo[2.2.1]hept-2-ene-2,7-dicarboxylate
• CAS: 208177-21-3
• 化学式: C₁₀H₁₂BrNO₄
• 分子量: 290.114
• InChiKey: OUFLGMYEKGTCLL-UHFFFAOYSA-N

物化性质

• 沸点：
  350.8±42.0 °C(Predicted)
• 密度：
  1.656±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3-bromo-7-azabicyclo[2.2.1]hept-2-ene-2,7-dicarboxylate 在 银 、 锌 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Synthesis and Dopamine Transporter Affinity of the Four Stereoisomers of (±)-2-(Methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane

  摘要：

  All four stereoisomers of (+/-)-2-(methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane were synthesized and evaluated as cocaine binding site ligands at the dopamine transporter. The in vitro binding affinities (K-i) of the 7-azabicyclo[2.2.1]heptane derivatives were measured in rat caudate-putamen tissue and found, to be 100-3000;fold less potent (K-i = 5-96 mu M) than cocaine and 2 beta-(methoxycarbonyl)-3 beta-phenyltropane (2, WIN 35,065-2). Surprisingly, the 3 alpha-phenyl isomers (6c, 6d) were more potent than the 3 beta-phenyl isomers (6a, 6b). Molecular modeling studies revealed that the rigid 7-azabicyclo[2.2. I]heptane derivatives possess molecular topologies which are significantly different than the molecular topologies of the 2 beta-(methoxycarbonyl)-3-phenyltropanes.

  DOI：

  10.1021/jm9705061
• 作为产物：
  描述：

  甲基吡咯-1-羧酸酯 在 盐酸 、 sodium tetrahydroborate 、 nickel diacetate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 57.0h， 生成 dimethyl 3-bromo-7-azabicyclo[2.2.1]hept-2-ene-2,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and Dopamine Transporter Affinity of the Four Stereoisomers of (±)-2-(Methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane

  摘要：

  All four stereoisomers of (+/-)-2-(methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane were synthesized and evaluated as cocaine binding site ligands at the dopamine transporter. The in vitro binding affinities (K-i) of the 7-azabicyclo[2.2.1]heptane derivatives were measured in rat caudate-putamen tissue and found, to be 100-3000;fold less potent (K-i = 5-96 mu M) than cocaine and 2 beta-(methoxycarbonyl)-3 beta-phenyltropane (2, WIN 35,065-2). Surprisingly, the 3 alpha-phenyl isomers (6c, 6d) were more potent than the 3 beta-phenyl isomers (6a, 6b). Molecular modeling studies revealed that the rigid 7-azabicyclo[2.2. I]heptane derivatives possess molecular topologies which are significantly different than the molecular topologies of the 2 beta-(methoxycarbonyl)-3-phenyltropanes.

  DOI：

  10.1021/jm9705061