benzyl N-[2-(6-methoxy-1H-indol-3-yl)ethyl]carbamate | 96096-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[2-(6-methoxy-1H-indol-3-yl)ethyl]carbamate
• CAS: 96096-66-1
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: BDTXNVZLKKHYSU-UHFFFAOYSA-N

物化性质

• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[2-(6-methoxy-1H-indol-3-yl)ethyl]carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 [2-(6-methoxy-indol-3-yl)-ethyl]-methyl-amine
  参考文献：
  名称：

  Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents

  摘要：

  Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.

  DOI：

  10.1021/jm00145a007
• 作为产物：
  描述：

  6-甲氧基吲哚 在 palladium on activated charcoal 叔丁基邻苯二酚 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 、 xylene 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 30.0h， 生成 benzyl N-[2-(6-methoxy-1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents

  摘要：

  Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.

  DOI：

  10.1021/jm00145a007