4-iodo-1-methoxy-3-(4-methoxyphenyl)-1H-pyrano[4,3-b]quinoline | 1235868-30-0

• 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-3-(4-methoxyphenyl)-1H-pyrano[4,3-b]quinoline
• CAS: 1235868-30-0
• 化学式: C₂₀H₁₆INO₃
• 分子量: 445.256
• InChiKey: MFWDPKCWSBTFKO-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  561.3±50.0 °C(predicted)
• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  丙烯酸丁酯 、 4-iodo-1-methoxy-3-(4-methoxyphenyl)-1H-pyrano[4,3-b]quinoline 在 trans-bis(triphenylphosphine)palladium dichloride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以68%的产率得到
  参考文献：
  名称：

  Pyrano[4,3-b]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions

  摘要：

  Synthesis of a 80-member library of novel pyrano[4,3-b]quinoline in solution-Phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electropHic iodocyclization of corresponding oho-alkynyl ' aldehydes in good to excellent yields under mild reaction,conditions. Subsequently a diverse set of libraries was generated by employing palladium:catalyzed Suzuki-Miyauta, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this:way,- a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.

  DOI：

  10.1021/co200100z
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 trans-bis(triphenylphosphine)palladium dichloride 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-iodo-1-methoxy-3-(4-methoxyphenyl)-1H-pyrano[4,3-b]quinoline
  参考文献：
  名称：

  Pyrano[4,3-b]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions

  摘要：

  Synthesis of a 80-member library of novel pyrano[4,3-b]quinoline in solution-Phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electropHic iodocyclization of corresponding oho-alkynyl ' aldehydes in good to excellent yields under mild reaction,conditions. Subsequently a diverse set of libraries was generated by employing palladium:catalyzed Suzuki-Miyauta, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this:way,- a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.

  DOI：

  10.1021/co200100z

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。
• Iodine-catalyzed and solvent-controlled selective electrophilic cyclization and oxidative esterification of ortho-alkynyl aldehydes
  作者：Akhilesh Kumar Verma、Trapti Aggarwal、Vineeta Rustagi、Richard C. Larock

  DOI：10.1039/b927185f

  日期：——

  4-Iodo-pyrano[4,3-b]quinolines and ortho-alkynyl esters were synthesized selectively from ortho-alkynyl aldehydes by an iodine-catalyzed and solvent controlled reaction.

  4-碘吡喃[4,3-b]喹啉和邻烷炔酯通过碘催化和溶剂控制反应，从邻烷炔醛中选择性合成。