dimethyl 1-(2-bromo-4,5-methylenedioxybenzyl)indole-2,3-dicarboxylate | 1314797-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: dimethyl 1-(2-bromo-4,5-methylenedioxybenzyl)indole-2,3-dicarboxylate
• 英文别名: Dimethyl 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]indole-2,3-dicarboxylate
• CAS: 1314797-91-5
• 化学式: C₂₀H₁₆BrNO₆
• 分子量: 446.254
• InChiKey: XKQQCBGXVSPVLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(2-bromo-4,5-methylenedioxybenzyl)indole-2,3-dicarboxylate 在 copper chromite 、 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 水 、 potassium acetate 作用下， 以 1,4-二氧六环 、 喹啉 为溶剂， 反应 13.5h， 生成 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：

  5-溴-6-溴甲基-1,3-苯并二氧杂环戊二烯 、 吲哚-2,3-二羧酸二甲酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 dimethyl 1-(2-bromo-4,5-methylenedioxybenzyl)indole-2,3-dicarboxylate
  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.