4-iodo-1-methoxy-8-methyl-3-phenethyl-1H-pyrano[4,3-b]quinoline | 1434153-20-4

• 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: 4-iodo-1-methoxy-8-methyl-3-phenethyl-1H-pyrano[4,3-b]quinoline
• CAS: 1434153-20-4
• 化学式: C₂₂H₂₀INO₂
• 分子量: 457.311
• InChiKey: FMMXEEUHHVEDHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  570.7±50.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  31.35
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  林可霉素 2,7-二乙酸酯 、 4-iodo-1-methoxy-8-methyl-3-phenethyl-1H-pyrano[4,3-b]quinoline 在 sodium acetate 、 palladium diacetate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以78%的产率得到4-benzyl-1,2-bis(4-methoxyphenyl)-8-methyl-3H-pyrrolo-[3,2,1-de]acridin-3-one
  参考文献：
  名称：

  Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

  摘要：

  An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodopyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process.

  DOI：

  10.1021/jo400539x
• 作为产物：
  描述：

  甲醇 、 6-methyl-2-(4-phenylbut-1-yn-1-yl)quinoline-3-carbaldehyde 在 碘 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到4-iodo-1-methoxy-8-methyl-3-phenethyl-1H-pyrano[4,3-b]quinoline
  参考文献：
  名称：

  Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

  摘要：

  An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodopyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process.

  DOI：

  10.1021/jo400539x