7H-9,10-methylenedioxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid | 1314797-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7H-9,10-methylenedioxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid
• 英文别名: 5,7-Dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,13,15(19),16-heptaene-13,14-dicarboxylic acid
• CAS: 1314797-95-9
• 化学式: C₁₈H₁₁NO₆
• 分子量: 337.288
• InChiKey: JWZOUOBXNJKKEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7H-9,10-methylenedioxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid 在 copper chromite 作用下， 以 喹啉 为溶剂， 反应 2.5h， 以13%的产率得到朱顶红定碱
  参考文献：
  名称：

  Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation

  摘要：

  The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.

  DOI：

  10.3987/com-11-12167
• 作为产物：
  描述：

  吲哚-2,3-二羧酸二甲酯 在 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 水 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 13.0h， 生成 7H-9,10-methylenedioxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid
  参考文献：
  名称：

  Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation

  摘要：

  The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.

  DOI：

  10.3987/com-11-12167

文献信息

• Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation
  作者：Yasuyoshi Miki、Hideaki Umemoto、Masashi Dohshita、Hiromi Hamamoto

  DOI：10.3987/com-11-12167

  日期：——

  The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.