Methyl (E)-3-[2-(t-butoxycarbonyl)vinyl]-4,5-dimethylpyrrole-2-carboxylate | 230645-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Methyl (E)-3-[2-(t-butoxycarbonyl)vinyl]-4,5-dimethylpyrrole-2-carboxylate
• CAS: 230645-71-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: AKOGMRAIKQUNQH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl (E)-3-[2-(t-butoxycarbonyl)vinyl]-4,5-dimethylpyrrole-2-carboxylate 在 甲酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 Methyl (E)-3-[N-(1-adamantyl)-2-carbamoylvinyl]-4,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  3-(2-Carbamoylvinyl)-4,5-dimethylpyrrole-2-carboxylic acids as ligands at the NMDA glycine-binding site: a study on the 2-carbamoylvinyl chain modification

  摘要：

  Twenty 4,5-dimethylpyrrole-2-carboxylic acids (5a-t) with different 2-carbamoylvinyl chains in position 3 were prepared to further investigate the relationships between structure and in vitro affinity for the strychnine-insensitive glycine-binding site. None of these compounds was superior to (E)-3-(N-phenyl-2-carbamoylvinyl)-4,5-dimethylpyrrole-2-carb oxylic acid III (pKi = 6.70), which was taken as a reference standard, but overall the results obtained indicate that the N-phenyl-2-carbamoylvinyl substituent of III may be replaced with the N-(1-adamantyl)-2-carbamoylvinyl group as in 5h (pKi = 6.20) without considerable loss of affinity. This finding adds to previous knowledge.

  DOI：

  10.1016/s0014-827x(98)00110-4
• 作为产物：
  描述：

  3-甲酰基-4,5-二甲基-1H-吡咯-2-羧酸甲酯 、 (叔丁氧基羰基甲基)三苯基溴化鏻 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.25h， 以78%的产率得到Methyl (E)-3-[2-(t-butoxycarbonyl)vinyl]-4,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  3-(2-Carbamoylvinyl)-4,5-dimethylpyrrole-2-carboxylic acids as ligands at the NMDA glycine-binding site: a study on the 2-carbamoylvinyl chain modification

  摘要：

  Twenty 4,5-dimethylpyrrole-2-carboxylic acids (5a-t) with different 2-carbamoylvinyl chains in position 3 were prepared to further investigate the relationships between structure and in vitro affinity for the strychnine-insensitive glycine-binding site. None of these compounds was superior to (E)-3-(N-phenyl-2-carbamoylvinyl)-4,5-dimethylpyrrole-2-carb oxylic acid III (pKi = 6.70), which was taken as a reference standard, but overall the results obtained indicate that the N-phenyl-2-carbamoylvinyl substituent of III may be replaced with the N-(1-adamantyl)-2-carbamoylvinyl group as in 5h (pKi = 6.20) without considerable loss of affinity. This finding adds to previous knowledge.

  DOI：

  10.1016/s0014-827x(98)00110-4