1-<(N-benzyl-N-methylamino)methyl>-4,5-(methylenedioxy)phthalide | 104834-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-<(N-benzyl-N-methylamino)methyl>-4,5-(methylenedioxy)phthalide
• 英文别名: 1-[(N-benzyl-N-methylamino)methyl]-4,5-(methylenedioxy)phthalide
• CAS: 104834-91-5
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: JXJGIOURKIYEGA-UHFFFAOYSA-N

物化性质

• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-<(N-benzyl-N-methylamino)methyl>-4,5-(methylenedioxy)phthalide 在 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 10.0h， 生成 4,5-(methylenedioxy)-1-<(N-methylamino)methyl>phthalan hydrochloride
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom

  摘要：

  The synthesis of a series of 1-(aminomethyl)phthalans 1b is reported. The radioligand binding to alpha 1- and alpha 2-receptors and the in vitro pharmacology in alpha 1 (rabbit aorta) and alpha 2 (phenoxybenzamine-pretreated dog saphenous vein) tissues were determined and were compared to the activity of the corresponding 1-(aminomethyl)indans. The activity of this series of phthalans was found to be consistent with the electrostatic repulsion hypothesis that was used to design the parent indan (ERBCOP) compounds. The effect of the phthalan ring oxygenation was to somewhat improve alpha 1-receptor potency relative to the 6-ERBCOP indans without having a general effect on the alpha 2-receptor potency. We conclude from the overall pattern of activity that while the norepinephrine type beta-hydroxyl group may be beneficial for binding to the alpha 1-adrenoceptor, it is not required for strong binding to or full stimulation of the alpha 2-adrenergic receptor, provided that the conformational mobility associated with the phenylethylamine is restricted and maintained in a favorable conformation for receptor interaction.

  DOI：

  10.1021/jm00384a030
• 作为产物：
  描述：

  5-formyl-benzo[1,3]dioxole-4-carboxylic acid 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 50.0 ℃ 、303.98 kPa 条件下， 反应 14.0h， 生成 1-<(N-benzyl-N-methylamino)methyl>-4,5-(methylenedioxy)phthalide
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom

  摘要：

  The synthesis of a series of 1-(aminomethyl)phthalans 1b is reported. The radioligand binding to alpha 1- and alpha 2-receptors and the in vitro pharmacology in alpha 1 (rabbit aorta) and alpha 2 (phenoxybenzamine-pretreated dog saphenous vein) tissues were determined and were compared to the activity of the corresponding 1-(aminomethyl)indans. The activity of this series of phthalans was found to be consistent with the electrostatic repulsion hypothesis that was used to design the parent indan (ERBCOP) compounds. The effect of the phthalan ring oxygenation was to somewhat improve alpha 1-receptor potency relative to the 6-ERBCOP indans without having a general effect on the alpha 2-receptor potency. We conclude from the overall pattern of activity that while the norepinephrine type beta-hydroxyl group may be beneficial for binding to the alpha 1-adrenoceptor, it is not required for strong binding to or full stimulation of the alpha 2-adrenergic receptor, provided that the conformational mobility associated with the phenylethylamine is restricted and maintained in a favorable conformation for receptor interaction.

  DOI：

  10.1021/jm00384a030