2-Fluoro-4-(1-pyrrolidinylcarbonyl)benzeneboronic acid | 874289-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Fluoro-4-(1-pyrrolidinylcarbonyl)benzeneboronic acid
• 英文别名: [2-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]boronic acid
• CAS: 874289-25-5
• 化学式: C₁₁H₁₃BFNO₃
• 分子量: 237.039
• InChiKey: XNEOXUHAOKJOON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴-3-氟苯甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 联硼酸频那醇酯 作用下， 以 2-甲基四氢呋喃 、 乙腈 为溶剂， 反应 32.0h， 生成 2-Fluoro-4-(1-pyrrolidinylcarbonyl)benzeneboronic acid
  参考文献：
  名称：

  A Robust Three-Step Telescoped Synthesis of Electron- Deficient Amide Substituted Arylboronic Acids

  摘要：

  A robust three-step telescoped process for the preparation of electron-deficient amide-substituted arylboronic acids from readily available bromobenzoic acids has been developed. An EDC-HOBT-promoted amide formation of a bromobenzoic acid was followed by subjection of the product stream to a palladium-mediated cross-coupling with B-2(pin)(2). The resultant mixture of the arylboronate ester and arylboronic acid was directly treated with NaIO4, followed by a heptane- MeTHF crystallization, to cleanly afford the corresponding arylboronic acid in good yield. This general procedure was used to synthesize electron-deficient amide-substituted arylboronic acids with a diverse array of electron-withdrawing substituents.

  DOI：

  10.1021/op100267p