8-iodo-7-phenyl-5H-pyrano[4,3-b]pyridin-5-one | 1159372-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 8-iodo-7-phenyl-5H-pyrano[4,3-b]pyridin-5-one
• 英文别名: 8-Iodo-7-phenylpyrano[4,3-b]pyridin-5-one
• CAS: 1159372-01-6
• 化学式: C₁₄H₈INO₂
• 分子量: 349.128
• InChiKey: YKKRHGSQLIWKPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 Oxone 、 四丁基碘化铵 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以64%的产率得到8-iodo-7-phenyl-5H-pyrano[4,3-b]pyridin-5-one
  参考文献：
  名称：

  Generation of 4-iodoisocoumarins through a TBAI-mediated oxidative cyclization of 2-alkynoates

  摘要：

  A tetra-butylammonium iodide (TBAI)-mediated oxidative iodocyclization of 2-alkynoates for the synthesis of various 4-iodoisocoumarin is described herein, and the reaction is highly efficient and shows broad functional group tolerance. This newly developed reaction uses a mixture of water and DCE as co-solvent, and avoids the use of iodine as iodine source for the electrophilic halocyclization.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1465094

文献信息

• Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach
  作者：Marine Peuchmaur、Vincent Lisowski、Céline Gandreuil、Ludovic T. Maillard、Jean Martinez、Jean-François Hernandez

  DOI：10.1021/jo900281a

  日期：2009.6.5

  A straightforward and traceless solid-phase methodology was developed for the synthesis of isocournarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.