(1R,5S)-3-propionyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one perchlorate | 1612797-49-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: (1R,5S)-3-propionyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one perchlorate
• CAS: 1612797-49-5
• 化学式: C₁₄H₁₈N₂O₂*ClHO₄
• 分子量: 346.768
• InChiKey: XIAQZNQCUMYMHC-VZXYPILPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.92
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131.72
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1R,5S)-3-propionyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one 在 高氯酸 作用下， 以 甲醇 为溶剂， 以75%的产率得到(1R,5S)-3-propionyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one perchlorate
  参考文献：
  名称：

  The amide protonation of (–)-N-benzoylcytisine in its perchlorate salts

  摘要：

  The C-13 NMR spectrum of (-)-N-benzoylcytisine perchlorate does not show a double set of signals typical of amide compounds, although this effect has been observed for the other diamine derivatives of cytisine. This observation means that in solution there must be the state of equilibrium between two forms of the cation with the protonated amide groups. DFT calculations have indeed indicated two preferred tautomeric forms with protonated oxygen atoms of amide groups. In the solid state however, according to X-ray analysis of perchlorate and perchlorate hydrate of N-benzoylcytisine the oxygen atom of the amide group in the six-membered ring A is preferred protonation site as compared with the oxygen in benzoic moiety. (-)-N-benzoylcytisine salt is the first compound from among the known derivatives of quinolizidine alkaloids that are not N-oxides, in which in solid state only the oxygen atom at cyclic amide is protonated instead of nitrogen atom or oxygen in benzoic moiety. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.02.192