3-氨基苯基三氟硼酸钾 | 1160186-73-1

• 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-氨基苯基三氟硼酸钾
• 英文名称: potassium 3-aminophenyltrifluoroborate
• 英文别名: Potassium (3-aminophenyl)trifluoroboranuide；potassium;(3-aminophenyl)-trifluoroboranuide
• CAS: 1160186-73-1
• 化学式: C₆H₆BF₃N*K
• mdl: MFCD09992971
• 分子量: 199.025
• InChiKey: GOLZDNNXPDXFRS-UHFFFAOYSA-N

物化性质

• 熔点：
  >186°C (dec.)
• 溶解度：
  DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  12
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基苯基三氟硼酸钾 、 水 在 montmorillonite K₁₀ 作用下， 反应 1.5h， 以78%的产率得到3-氨基苯硼酸
  参考文献：
  名称：

  An Efficient Method for the Hydrolysis of Potassium Organotrifluoroborates Promoted by Montmorillonite K10

  摘要：

  An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

  DOI：

  10.21577/0103-5053.20180126
• 作为产物：
  描述：

  3-氨基苯硼酸 在 potassium fluoride 、 L-酒石酸 作用下， 以 水 、 乙腈 、 四氢呋喃 为溶剂， 以76%的产率得到3-氨基苯基三氟硼酸钾
  参考文献：
  名称：

  Organotrifluoroborate盐的制备：降水驱动的平衡下，非蚀刻条件

  摘要：

  简便，快速，且可扩展：使用腐蚀性的HF / MF或MHF相反当前程序2种试剂（M =例如K），大范围的三氟硼酸的可迅速，简单地和安全地从MF（M = K，Cs的制备），RCO 2 H，和在常规的玻璃器皿一硼酸/硼酸酯（参见图;左与右）。的使用大号- （+） -酒石酸作为碱金属海绵是键，并且允许的RBF隔离3 M分别简单搅拌/过滤器/蒸发顺序。

  DOI：

  10.1002/anie.201203930

文献信息

• Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines
  作者：Geraint H. M. Davies、Asma Mukhtar、Borna Saeednia、Fatemeh Sherafat、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.joc.7b00747

  日期：2017.5.19

  boronic acids is described. An inexpensive, common reagent, SiO2, was found to serve as both a fluorophile and desiccant to facilitate the annulation process across three different azaborininone platforms. Computational analysis of some of the cores synthesized in this study was undertaken to compare the azaborininones with the analogous carbon-based heterocyclic systems. Computationally derived pKa values

  描述了一种使用简单的试剂和条件从有机三氟硼酸盐和硼酸两者中获得氮杂硼杂环丁酮（含羰基的硼基杂环支架）的方法。发现便宜的普通试剂SiO2既可以用作亲氟剂也可以用作干燥剂，以促进跨三个不同的氮杂硼氢化萘酮平台的成环过程。对本研究中合成的某些核进行了计算分析，以比较氮杂硼硼烷酮与类似的基于碳的杂环系统。通过计算得出的pKa值，NICS芳香度计算和静电势表面揭示了这些氮杂硼烷与它们的碳等排物之间独特的等电/同构关系，该关系根据硼的连通性而变化。
• Synthesis of Biphenyl Tyrosine Via Cross-Coupling Suzuki-Miyaura Reaction Using Aryltrifluoroborate Salts
  作者：Stanley N. S. Vasconcelos、Cristiane S. Barbeiro、Amna N. Khan、Hélio A. Stefani

  DOI：10.5935/0103-5053.20150038

  日期：——

  We reported a fast and easy method for obtaining biarylic units from tyrosine derivatives via Suzuki-Miyaura cross-coupling using a variety of substituted and unsubstituted potassium aryl-and heteroaryltrifluoroborate salts. The scope of the methodology was also extended to the formation of bis-tyrosine linked dipeptide bonds, leading to biologically interesting compounds. Some biarylic units were obtained as free amino acids through the one step cleavage reaction in good yields.
• Preparation of Organotrifluoroborate Salts: Precipitation-Driven Equilibrium under Non-Etching Conditions
  作者：Alastair J. J. Lennox、Guy C. Lloyd-Jones

  DOI：10.1002/anie.201203930

  日期：2012.9.10

  Simple, rapid, and scaleable: In contrast to current procedures using corrosive HF/MF or MHF2 reagents (M=e.g. K), a wide range of trifluoroborates can be rapidly, simply, and safely prepared from MF (M=K, Cs), RCO2H, and a boronic acid/ester in regular glassware (see figure; left versus right). The use of L‐(+)‐tartaric acid as an alkali‐metal sponge is key and allows isolation of RBF3M by a simple

  简便，快速，且可扩展：使用腐蚀性的HF / MF或MHF相反当前程序2种试剂（M =例如K），大范围的三氟硼酸的可迅速，简单地和安全地从MF（M = K，Cs的制备），RCO 2 H，和在常规的玻璃器皿一硼酸/硼酸酯（参见图;左与右）。的使用大号- （+） -酒石酸作为碱金属海绵是键，并且允许的RBF隔离3 M分别简单搅拌/过滤器/蒸发顺序。
• An Efficient Method for the Hydrolysis of Potassium Organotrifluoroborates Promoted by Montmorillonite K10
  作者：Renato Silva、Cosme Santos、Jonh Santos、Roberta Oliveira、Paulo Menezes、Juliano Freitas

  DOI：10.21577/0103-5053.20180126

  日期：——

  An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.