3-(4-bromophenyl)-2H-pyran-2-one | 1256469-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(4-bromophenyl)-2H-pyran-2-one
• 英文别名: 3-(4-Bromophenyl)pyran-2-one
• CAS: 1256469-37-0
• 化学式: C₁₁H₇BrO₂
• 分子量: 251.079
• InChiKey: SWVCHOXRUHTGEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-oxo-2H-pyran-3-yl trifluoromethanesulfonate 、 4-溴苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以83%的产率得到3-(4-bromophenyl)-2H-pyran-2-one
  参考文献：
  名称：

  A Concise Access to 3-Substituted 2-Pyrones.

  摘要：

  The development of a modular synthesis of 3-substituted-2-pyrones is described The attainment of this strategy hinges on a new electrophilic pyrone derivative which can be readily prepared on a multigram scale and which performs very competently in metal-catalyzed cross-coupling reactions with a variety of nucleophiles

  DOI：

  10.1021/jo101843a

文献信息

• Synthesis of 3-Aryl-2-pyrones by Palladium-Catalyzed Cross-Coupling of Aryl Iodides with Cyclic Vinyldiazo Ester
  作者：Jun Huang、Linyong Li、Haoguo Chen、Tiebo Xiao、Yuwei He、Lei Zhou

  DOI：10.1021/acs.joc.7b01470

  日期：2017.9.1

  A palladium-catalyzed cross-coupling reaction of aryl iodides with cyclic vinyldiazo ester was developed. The reaction provides various 3-aryl-2-pyrones in good yields with high functional group tolerance. The synthetic application of the resulting 3-aryl-2-pyrones as the diene component in a Diels–Alder reaction was also described.

  开发了钯催化的芳基碘化物与环状乙烯基重氮酯的交叉偶联反应。该反应以高收率和高官能团耐受性提供了各种3-芳基-2-吡喃酮。还描述了在狄尔斯-阿尔德反应中合成的3-芳基-2-吡喃酮作为二烯组分的合成应用。
• A Concise Access to 3-Substituted 2-Pyrones.
  作者：Frédéric Frébault、Maria Teresa Oliveira、Eckhard Wöstefeld、Nuno Maulide

  DOI：10.1021/jo101843a

  日期：2010.11.19

  The development of a modular synthesis of 3-substituted-2-pyrones is described The attainment of this strategy hinges on a new electrophilic pyrone derivative which can be readily prepared on a multigram scale and which performs very competently in metal-catalyzed cross-coupling reactions with a variety of nucleophiles