8-bromo-2-hydroxy-2-phenylnaphtho[2,1-b]furan-1(2H)-one | 1574190-63-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 8-bromo-2-hydroxy-2-phenylnaphtho[2,1-b]furan-1(2H)-one
• CAS: 1574190-63-8
• 化学式: C₁₈H₁₁BrO₃
• 分子量: 355.188
• InChiKey: DKRRLYIXMVHBHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-溴-7-羟基萘 、 苯乙酮 在 碘 、 二甲基亚砜 作用下， 反应 48.0h， 以62%的产率得到8-bromo-2-hydroxy-2-phenylnaphtho[2,1-b]furan-1(2H)-one
  参考文献：
  名称：

  I₂-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-b]furan-1(2H)-ones with a Quaternary Center

  摘要：

  A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel-Crafts/oxidation/cyclization mechanism was proposed.

  DOI：

  10.1021/ol5004093