2-(6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-diisopropyl-2-oxo-acetamide | 82173-77-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 2-(6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-diisopropyl-2-oxo-acetamide
• 英文别名: 2-(6H-[1,3]dioxolo[4,5-e]indol-8-yl)-2-oxo-N,N-di(propan-2-yl)acetamide
• CAS: 82173-77-1
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: LJNWFKUGUAWPSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-diisopropyl-2-oxo-acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以31%的产率得到N-[2-(6H-[1,3]dioxolo[4,5-e]indol-8-yl)ethyl]-N-propan-2-ylpropan-2-amine
  参考文献：
  名称：

  Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

  摘要：

  A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.

  DOI：

  10.1021/jm00350a005
• 作为产物：
  描述：

  4-甲基-1,3-苯并二氧戊环 在 palladium on activated charcoal mercury(II) diacetate 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 80.0 ℃ 、303.98 kPa 条件下， 反应 13.5h， 生成 2-(6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-diisopropyl-2-oxo-acetamide
  参考文献：
  名称：

  Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

  摘要：

  A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.

  DOI：

  10.1021/jm00350a005