(2-氟-1,4-苯基)二硼酸 | 1380435-64-2

• 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: (2-氟-1,4-苯基)二硼酸
• 英文名称: 2-fluoro-1,4-phenylenediboronic acid
• 英文别名: boronic acid；(2-Fluoro-1,4-phenylene)diboronic acid；(4-borono-2-fluorophenyl)boronic acid
• CAS: 1380435-64-2
• 化学式: C₆H₇B₂FO₄
• 分子量: 183.74
• InChiKey: PSBUHLOCAVSTMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  420.3±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.81
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-硝基碘苯 、 (2-氟-1,4-苯基)二硼酸 在 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以29%的产率得到2-fluoro-2,2''-dinitro-1,1'':4',1''-terphenyl
  参考文献：
  名称：

  星形孢菌素糖苷配基K252c的吡唑类似物的合成及生物活性

  摘要：

  合成了星形孢菌素糖苷配基（K252c）的衍生物，其中内酰胺环被吡唑部分取代。生成的吲哚并吡唑并咔唑（3）抑制了Pim同工型1-3，但并未损害K252c的两个已知靶标蛋白激酶C同工型α和γ的活性。化合物3对人白血病和结肠癌细胞系（K562和HCT116）表现出中等的细胞毒活性，强烈表明这种新支架值得进一步研究以治疗与Pim活性相关的恶性肿瘤。

  DOI：

  10.1016/j.bmc.2016.05.032
• 作为产物：
  描述：

  1,4-二溴-2-氟苯 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到(2-氟-1,4-苯基)二硼酸
  参考文献：
  名称：

  Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic Acids

  摘要：

  The results of X-ray crystallographic and computational studies of a series of fluorinated 1,4-phenylenediboronic acids (i.e., fluoro-1,4-phenylenediboronic acid, 2,6-difluoro-1,4-phenylenediboronic acid, 2,3-difluoro-1,4-phenylenediboronic acid, 2,5-difluoro-1,4-phenylenediboronic acid, and tetrafluoro-1,4-phenylenediboronic acid) are reported. The effect of fluorine substitution on crystal organization in the presence of strong and directional hydrogen bonds was studied. Comparison with the two previously reported forms of the unsubstituted 1,4-phenylenediboronic acid revealed a strong relation between a supramolecular network and the number of water molecules present in the crystal lattice. As indicated by the theoretical calculations performed in the CRYSTAL and PIXEL programs, the structures with greater amount of water are better stabilized (from about -170 kJ.mol(-1) for anhydrous forms to about -420 kJ.mol(-1) for tetrahydrate). The energy of hydrogen bonded dimers vary from -40 kJ.mol(-1) to -50 kJ.mol(-1). Contacts with fluorine atoms play rather a secondary role in the crystal packing. Fluorine substituents tend to interact with the electropositive boron atom. Furthermore, intramolecular interactions significantly affect the torsion angle of the B(OH)(2) group. The constrained energy scan revealed that stronger interactions with substituents stabilize the planar conformation and hamper the rotation of the boronic group. This in turn has a further impact on the interactions within selected crystal motifs and supposedly rules the proton disorder within boronic fragments. Besides the interactions with the fluorine atoms, other weak contacts such as C(pi)center dot center dot center dot B and O center dot center dot center dot B also influence the molecular organization. The energy of the corresponding dimers varies from -15 kJ.mol(-1) to -25 kJ.mol(-1).

  DOI：

  10.1021/cg3005272