7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one | 1227474-46-5

• 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: 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one
• 英文别名: 7-methoxy-8-(4-methylfuran-3-yl)-2H-chromen-2-one；7-Methoxy-8-(4-methylfuran-3-yl)chromen-2-one
• CAS: 1227474-46-5
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: INZNSTVWSRDWLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-Iodo-4-methylfuran 在 bis-triphenylphosphine-palladium(II) chloride 、 叔丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲苯 、 正戊烷 为溶剂， 反应 18.25h， 生成 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of 8-Aryl-Substituted Coumarins Based on Ring-Closing Metathesis and Suzuki–Miyaura Coupling: Synthesis of a Furyl Coumarin Natural Product from Galipea panamensis

  摘要：

  The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an 8-halocoumarin, which is advantageously synthesized using a ring-closing metathesis reaction. Several non-natural analogues are also available along these lines.

  DOI：

  10.1021/jo2026564

文献信息

• Synthesis of 8-Aryl-Substituted Coumarins Based on Ring-Closing Metathesis and Suzuki–Miyaura Coupling: Synthesis of a Furyl Coumarin Natural Product from <i>Galipea panamensis</i>
  作者：Bernd Schmidt、Stefan Krehl、Alexandra Kelling、Uwe Schilde

  DOI：10.1021/jo2026564

  日期：2012.3.2

  The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an 8-halocoumarin, which is advantageously synthesized using a ring-closing metathesis reaction. Several non-natural analogues are also available along these lines.