dimethyl 7-bromo-1-(4,5-dimethoxybenzyl)indole-2,3-dicarboxylate | 1314797-85-7

• 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 7-bromo-1-(4,5-dimethoxybenzyl)indole-2,3-dicarboxylate
• 英文别名: Dimethyl 7-bromo-1-[(3,4-dimethoxyphenyl)methyl]indole-2,3-dicarboxylate；dimethyl 7-bromo-1-[(3,4-dimethoxyphenyl)methyl]indole-2,3-dicarboxylate
• CAS: 1314797-85-7
• 化学式: C₂₁H₂₀BrNO₆
• 分子量: 462.297
• InChiKey: YVWIZCLATDRSBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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 7-bromo-1-(4,5-dimethoxybenzyl)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 13.0h， 生成 pratosine
  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：

  dimethyl 7-bromoindole-2,3-dicarboxylate 、 3,4-二甲氧基苄氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 22.0h， 以59%的产率得到dimethyl 7-bromo-1-(4,5-dimethoxybenzyl)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.