3-氟-5-(1-吡咯烷基羰基)苯硼酸 | 1264616-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氟-5-(1-吡咯烷基羰基)苯硼酸
• 英文名称: 3-Fluoro-5-(1-pyrrolidinylcarbonyl)benzeneboronic acid
• 英文别名: [3-fluoro-5-(pyrrolidine-1-carbonyl)phenyl]boronic acid
• CAS: 1264616-18-3
• 化学式: C₁₁H₁₃BFNO₃
• 分子量: 237.039
• InChiKey: XPUNUDDGDYAOFL-UHFFFAOYSA-N

物化性质

• 熔点：
  110.3 °C
• 沸点：
  473.2±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

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：

  3-溴-5-氟苯甲酸 、 四氢吡咯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 联硼酸频那醇酯 、 盐酸 、 sodium periodate 作用下， 以 乙腈 、 2-甲基四氢呋喃 、 水 为溶剂， 以45%的产率得到3-氟-5-(1-吡咯烷基羰基)苯硼酸
  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

文献信息

• A Robust Three-Step Telescoped Synthesis of Electron- Deficient Amide Substituted Arylboronic Acids
  作者：Jason Zhu、Thomas M. Razler、Zhongmin Xu、David A. Conlon、Eric W. Sortore、Alan W. Fritz、Roman Demerzhan、Jason T. Sweeney

  DOI：10.1021/op100267p

  日期：2011.3.18

  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.