4-(4-ethylphenyl)-1-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline | 1256286-30-2

• 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-(4-ethylphenyl)-1-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline
• CAS: 1256286-30-2
• 化学式: C₂₇H₂₃NO₂
• 分子量: 393.485
• InChiKey: OEYPANYPSDSZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 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 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-(4-ethylphenyl)-1-methoxy-3-phenyl-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

• 2-(1-Benzotriazolyl)pyridine: A Robust Bidentate Ligand for the Palladium-Catalyzed CC (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), CN and CS Coupling Reactions
  作者：Akhilesh K. Verma、Rajeev R. Jha、Ritu Chaudhary、Rakesh K. Tiwari、Abhinandan K. Danodia

  DOI：10.1002/adsc.201200583

  日期：2013.2.1

  designed and employed for the palladium-catalyzed CC (Suzuki, Heck, Fujiwara–Moritani, and Sonogashira), CN and CS coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the

  设计了一种新型的双齿配体1-（吡啶-2-基）-1 H-苯并[ d ] [1,2,3]三唑，并用于钯催化的CC（Suzuki，Heck，Fujiwara– Moritani和Sonogashira），CN和CS偶联反应。发现该配体便宜，热稳定，易于以几克规模由容易获得的起始原料合成，显示出使用简单性和在应用中的坚固性，从而使该配体对于不同的偶联反应有效。适当地，苯并三唑环的NN键的供体能力和吡啶环的N上的孤对电子增强了配体的二齿能力。
• Iodine-Mediated Solvent-Controlled Selective Electrophilic Cyclization and Oxidative Esterification of <i>o</i>-Alkynyl Aldehydes: An Easy Access to Pyranoquinolines, Pyranoquinolinones, and Isocumarins
  作者：Akhilesh K. Verma、Vineeta Rustagi、Trapti Aggarwal、Amit P. Singh

  DOI：10.1021/jo101526b

  日期：2010.11.19

  provides pyrano[4,3-b]quinolines 4a−f, via formation of cyclic iodonium intermediate Q; however, using alcohols as a solvent as well as nucleophile, o-alkynyl esters 5a−y were obtained selectively in good to excellent yields via formation of hypoiodide intermediate R. Subsequently, o-alkynyl esters were converted in to pyranoquinolinones 6a−i and isocoumarin 6j by electrophilic iodocyclization. This

  描述了碘在邻炔基醛的亲电碘环化中在不同溶剂中的化学选择性行为。与CH 2 Cl 2中的I 2与适当的亲核试剂反应生成邻炔基醛3a - t可以通过形成环碘鎓中间体Q生成吡喃并[4,3- b ]喹啉4a - f；但是，使用醇和亲核试剂作为溶剂，通过形成次碘化物中间体，选择性地以良好或优异的收率获得了邻炔基酯5a - y。[R 。随后，通过亲电碘环化将邻炔基酯转化为吡喃喹啉酮6a - i和异香豆素6j。这种发达的氧化酯化反应为从醛3n - p化学选择性合成酯5q - u而不氧化底物中存在的伯醇提供了新途径。
• Pyrano[4,3-<i>b</i>]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions
  作者：Trapti Aggarwal、Maryam Imam、Naveen K. Kaushik、Virander S. Chauhan、Akhilesh K. Verma

  DOI：10.1021/co200100z

  日期：2011.9.12

  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 63} and 621} and Heck coupling product 812} exhibit promising antimalarial activity.