Trifluoro-(3-nitrophenyl)boranuide

• 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: Trifluoro-(3-nitrophenyl)boranuide
• 化学式: C₆H₄BF₃NO₂
• 分子量: 189.909
• InChiKey: TYZCSDLQOARYDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Trifluoro-(3-nitrophenyl)boranuide 以 phosphate buffer 为溶剂， 生成 3-硝基苯硼酸
  参考文献：
  名称：

  Substituent Effects on Aryltrifluoroborate Solvolysis in Water: Implications for Suzuki−Miyaura Coupling and the Design of Stable ¹⁸F-Labeled Aryltrifluoroborates for Use in PET Imaging

  摘要：

  Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.

  DOI：

  10.1021/jo800681d
• 作为产物：
  描述：

  3-硝基苯硼酸 在 氢氟酸 作用下， 以 水 为溶剂， 生成 Trifluoro-(3-nitrophenyl)boranuide 、 、
  参考文献：
  名称：

  取代基和溶剂对有机硼酸与氟化物反应的影响

  摘要：

  引入吸电子取代基或质子化以带正电并可能参与氢键的取代基的引入增强了苯基硼酸与氟化物的反应性。使用 60% 的 MeOH 水溶液可抑制带负电荷物质的形成，无论它们的结构是三角还是四面体，但由于氟化物的溶剂化较少，因此提高了整体反应性。

  DOI：

  10.1246/bcsj.74.509

文献信息

• Substituent Effects on Aryltrifluoroborate Solvolysis in Water: Implications for Suzuki−Miyaura Coupling and the Design of Stable ¹⁸F-Labeled Aryltrifluoroborates for Use in PET Imaging
  作者：Richard Ting、Curtis W. Harwig、Justin Lo、Ying Li、Michael J. Adam、Thomas J. Ruth、David M. Perrin

  DOI：10.1021/jo800681d

  日期：2008.6.1

  Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including F-18-labeled PET reagents and has mechanistic implications for ArBF3-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.
• Substituent and Solvent Effects on the Reactions of Organoboronic Acids with Fluoride
  作者：Akio Yuchi、Atsushi Tatebe、Shinpei Kani、Tony D. James

  DOI：10.1246/bcsj.74.509

  日期：2001.3

  The introduction of an electron-withdrawing substituent or a substituent protonated to be positively charged and potentially involved in hydrogen bonding enhances the reactivities of phenylboronic acids with fluoride. The use of a 60% aqueous MeOH medium suppresses the formation of the negatively charged species, irrespective of whether their structures are trigonal or tetrahedral, but enhances the

  引入吸电子取代基或质子化以带正电并可能参与氢键的取代基的引入增强了苯基硼酸与氟化物的反应性。使用 60% 的 MeOH 水溶液可抑制带负电荷物质的形成，无论它们的结构是三角还是四面体，但由于氟化物的溶剂化较少，因此提高了整体反应性。