7H-9,10-dimethoxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid | 1314797-90-4

• 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-dimethoxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid
• 英文别名: 9,10-dimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid；4,5-Dimethoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,4,6,10,12(16),13-heptaene-10,11-dicarboxylic acid；4,5-dimethoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,4,6,10,12(16),13-heptaene-10,11-dicarboxylic acid
• CAS: 1314797-90-4
• 化学式: C₁₉H₁₅NO₆
• 分子量: 353.331
• InChiKey: GSVJOMPSTBUSGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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-dimethoxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid 在 sodium tetrahydroborate 、 碘苯二乙酸 、 palladium 10% on activated carbon 、 potassium bromide 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 2,2,2-三氟乙醇 为溶剂， 反应 9.0h， 生成 pratosine
  参考文献：
  名称：

  Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction

  摘要：

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.132
• 作为产物：
  描述：

  3,4-二甲氧基苄氯 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 、 丙酮 为溶剂， 反应 34.0h， 生成 7H-9,10-dimethoxypyrrolo[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.
• Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction
  作者：Yasuyoshi Miki、Hideaki Umemoto、Masashi Dohshita、Hiromi Hamamoto

  DOI：10.1016/j.tetlet.2012.01.132

  日期：2012.4

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.