(1'S)-hydroxy-3',4'-didehydrostemofoline | 1227062-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S)-hydroxy-3',4'-didehydrostemofoline
• CAS: 1227062-70-5
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: JSWHBVQUNCYCQO-HZNICZTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1'S)-hydroxy-3',4'-didehydrostemofoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以40%的产率得到(1'S)-hydroxystemofoline
  参考文献：
  名称：

  Semisynthesis and Acetylcholinesterase Inhibitory Activity of Stemofoline Alkaloids and Analogues

  摘要：

  Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.

  DOI：

  10.1021/np100137h
• 作为产物：
  描述：

  (1'S)-acetoxy-3',4'-didehydrostemofoline 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以73%的产率得到(1'S)-hydroxy-3',4'-didehydrostemofoline
  参考文献：
  名称：

  Semisynthesis and Acetylcholinesterase Inhibitory Activity of Stemofoline Alkaloids and Analogues

  摘要：

  Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.

  DOI：

  10.1021/np100137h