6-hydroxy-8-oxoprotoberberine | 144709-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-hydroxy-8-oxoprotoberberine
• 英文别名: 6-Hydroxy-2,3-dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one
• CAS: 144709-17-1
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: BKHHJVTZEILANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [4,5-Dimethoxy-2-(1-oxo-1,2-dihydro-isoquinolin-3-yl)-phenyl]-acetic acid 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 calcium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 6-hydroxy-8-oxoprotoberberine
  参考文献：
  名称：

  A common and general access to berberine and benzo [c] phenanthridine alkaloids

  摘要：

  The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.

  DOI：

  10.1016/s0040-4020(01)80496-8

文献信息

• A common and general access to berberine and benzo [c] phenanthridine alkaloids
  作者：René Beugelmans、Michèle Bois-Choussy

  DOI：10.1016/s0040-4020(01)80496-8

  日期：1992.1

  The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a high-yielding and versatile access to both classes of alkaloids.