6-methoxy-3-(dipropylamino)-2H-1-benzopyran | 112460-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methoxy-3-(dipropylamino)-2H-1-benzopyran
• 英文别名: 6-methoxy-N,N-dipropyl-2H-chromen-3-amine
• CAS: 112460-75-0
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: AVIFHQDGAACMKU-UHFFFAOYSA-N

物化性质

• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(dipropylamino)-2H-1-benzopyran 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到6-methoxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran
  参考文献：
  名称：

  6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine agonists with autoreceptor selectivity

  摘要：

  The dopamine agonist profiles of 3,4-dihydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and -8-ol (4 and 5, respectively) were examined. Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand [3H]propylnorapomorphine than for those labeled with the dopamine antagonist ligand [3H]haloperidol. Both compounds attenuated the stimulation of brain dopamine synthesis caused by gamma-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats. This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

  DOI：

  10.1021/jm00398a032
• 作为产物：
  描述：

  6-甲氧基-2H-苯并吡喃-3-羧酸 在 盐酸 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 戊醇 、 溶剂黄146 为溶剂， 反应 7.5h， 生成 6-methoxy-3-(dipropylamino)-2H-1-benzopyran
  参考文献：
  名称：

  6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine agonists with autoreceptor selectivity

  摘要：

  The dopamine agonist profiles of 3,4-dihydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and -8-ol (4 and 5, respectively) were examined. Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand [3H]propylnorapomorphine than for those labeled with the dopamine antagonist ligand [3H]haloperidol. Both compounds attenuated the stimulation of brain dopamine synthesis caused by gamma-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats. This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

  DOI：

  10.1021/jm00398a032