4-methoxy-3-phenylethynylcoumarin | 1073128-26-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methoxy-3-phenylethynylcoumarin
• 英文别名: 4-Methoxy-3-(2-phenylethynyl)chromen-2-one
• CAS: 1073128-26-3
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: SENDUEBQUQNIKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-phenylethynylcoumarin 在 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以85%的产率得到3-iodo-2-phenyl-4H-furo[2,3-b][1]benzopyran-4-one
  参考文献：
  名称：

  A Pd-Catalyzed Heteroannulation Approach to 2,3-Disubstituted Furo[3,2-c]coumarins

  摘要：

  The Pd-catalyzed cyclofunctionalization of 3-alkynyl-4-methoxycoumarins with aryl halides resulted In the selective formation of 3-arylfuro[3,2-c]coumarins in lieu of the expected regioisomeric 3-arylfuro[2,3-b]chromones. A mechanism involving the linear to angular rearrangement of a Pd-containing furan intermediate was proposed.

  DOI：

  10.1021/ol902189q
• 作为产物：
  描述：

  苯乙炔 、 3-iodo-4-methoxycoumarin 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到4-methoxy-3-phenylethynylcoumarin
  参考文献：
  名称：

  Et₃N-Induced Demethylation−Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles

  摘要：

  Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling. dealkylation, and regioselective furan annulation reactions. A Et3N-induced S(N)2 process has been established that accounts for the dealkylation process.

  DOI：

  10.1021/jo8014038

文献信息

• Iodocyclization versus diiodination in the reaction of 3-alkynyl-4-methoxycoumarins with iodine: Synthesis of 3-iodofuro[2,3-b]chromones
  作者：Guillaume Raffa、Sébastien Belot、Geneviève Balme、Nuno Monteiro

  DOI：10.1039/c0ob00935k

  日期：——

  The reaction of 3-alkynyl-4-methoxycoumarins with molecular iodine in chlorinated solvents allows access to 3-iodofurochromones in good to excellent yields as the result of a iodocyclization–demethylation process. Competitive diiodination of the coumarin acetylene moiety could be eliminated by simply performing the reactions in refluxing 1,2-dichloroethane, owing to the thermal instability of the resulting (E)-1,2-diiodoethenylcoumarins.

  3-烷炔基-4-甲氧基香豆素与分子碘在氯化溶剂中的反应可以通过碘环化-去甲基化过程获得3-碘代呋喃色素，产率良好到优异。由于生成的(E)-1,2-二碘乙烯基香豆素的热不稳定性，通过简单地在回流的1,2-二氯乙烷中进行反应，可以消除香豆素炔烃部分的竞争性二碘化。
• A Pd-Catalyzed Heteroannulation Approach to 2,3-Disubstituted Furo[3,2-<i>c</i>]coumarins
  作者：Guillaume Raffa、Marion Rusch、Geneviève Balme、Nuno Monteiro

  DOI：10.1021/ol902189q

  日期：2009.11.19

  The Pd-catalyzed cyclofunctionalization of 3-alkynyl-4-methoxycoumarins with aryl halides resulted In the selective formation of 3-arylfuro[3,2-c]coumarins in lieu of the expected regioisomeric 3-arylfuro[2,3-b]chromones. A mechanism involving the linear to angular rearrangement of a Pd-containing furan intermediate was proposed.
• Et₃N-Induced Demethylation−Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles
  作者：David Conreaux、Sébastien Belot、Philippe Desbordes、Nuno Monteiro、Geneviève Balme

  DOI：10.1021/jo8014038

  日期：2008.11.7

  Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling. dealkylation, and regioselective furan annulation reactions. A Et3N-induced S(N)2 process has been established that accounts for the dealkylation process.