N-methyl-3-<2-(hydroxyethyl)-4,5-dimethoxyphenyl>-7,8-dimethoxy-1(2H)-isoquinolone | 144709-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-methyl-3-<2-(hydroxyethyl)-4,5-dimethoxyphenyl>-7,8-dimethoxy-1(2H)-isoquinolone
• 英文别名: 3-[2-(2-Hydroxyethyl)-4,5-dimethoxyphenyl]-7,8-dimethoxy-2-methylisoquinolin-1-one
• CAS: 144709-32-0
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: HYZHLHJAVZRASM-UHFFFAOYSA-N

物化性质

• 沸点：
  623.3±55.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methyl-3-<2-(hydroxyethyl)-4,5-dimethoxyphenyl>-7,8-dimethoxy-1(2H)-isoquinolone 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到2,3,7,8-tetramethoxy-5-methyl-6-oxo-benzophenanthridine
  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
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸甲酯 在 盐酸 、 lithium aluminium tetrahydride 、 高氯酸 、 三氟化硼乙醚 、 potassium tert-butylate 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-methyl-3-<2-(hydroxyethyl)-4,5-dimethoxyphenyl>-7,8-dimethoxy-1(2H)-isoquinolone
  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.