2-hydroxyberbin-8-one | 147919-72-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 2-hydroxyberbin-8-one
• CAS: 147919-72-0
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: AANLABWQJWMNST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyberbin-8-one 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 2-methoxyberbine
  参考文献：
  名称：

  Selective Acetylation of Berbin-8-one. Synthesis of 2-Methoxyberbine

  摘要：

  In the presence of excess aluminum chloride, berbin-8-one (1) could be selectively acetylated at the C-2 position to give 2-acetylberbin-8-one (2) in good yield. In fact this exclusive orientation was due to a complex between the amide carbonyl and the Lewis acid which deactivated the aromatic ring D for electrophilic substitution. Further chemical degradation of the acetyl group afforded the corresponding phenol derivative (3) which was converted to 2-methoxyberbin-8-one (4). Reduction of this latter gave finally 2-methoxyberbine (5). Spectral data comparison of compound (4) and 3-methoxyberbin-8-one permitted us to conclude unambiguously in favour of the C-2 orientation of the acetylation.

  DOI：

  10.3987/com-92-6240
• 作为产物：
  描述：

  5,6,13,13a-Tetrahydro-8H-dibenzo[a,g]chinolizin-8-on 在 三氯化铝 、 双氧水 、 三氟乙酸酐 作用下， 以 二硫化碳 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2-hydroxyberbin-8-one
  参考文献：
  名称：

  Selective Acetylation of Berbin-8-one. Synthesis of 2-Methoxyberbine

  摘要：

  In the presence of excess aluminum chloride, berbin-8-one (1) could be selectively acetylated at the C-2 position to give 2-acetylberbin-8-one (2) in good yield. In fact this exclusive orientation was due to a complex between the amide carbonyl and the Lewis acid which deactivated the aromatic ring D for electrophilic substitution. Further chemical degradation of the acetyl group afforded the corresponding phenol derivative (3) which was converted to 2-methoxyberbin-8-one (4). Reduction of this latter gave finally 2-methoxyberbine (5). Spectral data comparison of compound (4) and 3-methoxyberbin-8-one permitted us to conclude unambiguously in favour of the C-2 orientation of the acetylation.

  DOI：

  10.3987/com-92-6240