3-butyl-4-iodo-1-methoxy-8-methyl-1H-pyrano[4,3-b]quinoline | 1401829-19-3

• 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: 3-butyl-4-iodo-1-methoxy-8-methyl-1H-pyrano[4,3-b]quinoline
• CAS: 1401829-19-3
• 化学式: C₁₈H₂₀INO₂
• 分子量: 409.267
• InChiKey: VWKDRVSFDTXXHO-UHFFFAOYSA-N

物化性质

• 沸点：
  495.3±45.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  1,1'-(1,2-乙炔二基)二(4-甲基苯) 、 3-butyl-4-iodo-1-methoxy-8-methyl-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 0.42h， 以72%的产率得到8-methyl-4-propyl-1,2-di-p-tolyl-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 、 2-(hex-1-yn-1-yl)-6-methylquinoline-3-carbaldehyde 在 碘 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 3-butyl-4-iodo-1-methoxy-8-methyl-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

文献信息

• Palladium-Catalyzed Regioselective [3 + 2] Annulation of Internal Alkynes and Iodo-pyranoquinolines with Concomitant Ring Opening
  作者：Trapti Aggarwal、Rajeev R. Jha、Rakesh K. Tiwari、Sonu Kumar、Siva K. Reddy Kotla、Sushil Kumar、Akhilesh K. Verma

  DOI：10.1021/ol3022935

  日期：2012.10.19

  A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive

  通过钯催化的[3 + 2]碘-吡喃喹啉和内部炔烃的开环反应，通过新颖的策略开发了高度官能化的吡咯并[1,2- a ]喹啉的区域选择性串联合成。在3位上有正烷基取代的吡喃喹啉通过[3 + 2]环空/开环和连续的分子内跨羟醛缩合反应导致吡咯烷-rid啶酮的形成。