N-isopropyl-N-(2-(5-nitrobenzo[d][1,2,3]dioxaborol-2-yl)benzyl)propan-2-amine | 1155805-45-0

• 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: N-isopropyl-N-(2-(5-nitrobenzo[d][1,2,3]dioxaborol-2-yl)benzyl)propan-2-amine
• 英文别名: N-[[2-(5-nitro-1,3,2-benzodioxaborol-2-yl)phenyl]methyl]-N-propan-2-ylpropan-2-amine
• CAS: 1155805-45-0
• 化学式: C₁₉H₂₃BN₂O₄
• 分子量: 354.214
• InChiKey: RTDPNZRTVRLTQV-UHFFFAOYSA-N

物化性质

• 沸点：
  443.3±55.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-((二异丙基氨基)甲基)苯硼酸 、 4-硝基儿茶酚 在 magnesium sulfate 作用下， 以 氯仿 为溶剂， 生成 N-isopropyl-N-(2-(5-nitrobenzo[d][1,2,3]dioxaborol-2-yl)benzyl)propan-2-amine
  参考文献：
  名称：

  Probing Intramolecular B−N Interactions in Ortho-Aminomethyl Arylboronic Acids

  摘要：

  This work investigates the interplay between the intramolecular B-N dative bonding and solvent insertion in various ortho-methylamino arylboronic acids in protic media. B-11 NMR experiments were conducted to study the effect that the degree of substitution of the amine group has on B-N bonding versus solvent insertion. It was found that there is a slight increase in the amount of B-N dative bonding on going from a tertiary to a secondary to a primary amine group, but that solvent insertion dominates in all cases of the boronate esters. A X-ray crystal structure gives further insight into the structure of the solvent-inserted boronate esters, showing that the inserted solvent has its hydrogen primarily on the amine. Lastly, studies of the use of boronate esters as receptors for simple alcohols and carboxylic acids are described.

  DOI：

  10.1021/jo900187a

文献信息

• Probing Intramolecular B−N Interactions in <i>Ortho</i>-Aminomethyl Arylboronic Acids
  作者：Byron E. Collins、Steven Sorey、Amanda E. Hargrove、Shagufta H. Shabbir、Vincent M. Lynch、Eric V. Anslyn

  DOI：10.1021/jo900187a

  日期：2009.6.5

  This work investigates the interplay between the intramolecular B-N dative bonding and solvent insertion in various ortho-methylamino arylboronic acids in protic media. B-11 NMR experiments were conducted to study the effect that the degree of substitution of the amine group has on B-N bonding versus solvent insertion. It was found that there is a slight increase in the amount of B-N dative bonding on going from a tertiary to a secondary to a primary amine group, but that solvent insertion dominates in all cases of the boronate esters. A X-ray crystal structure gives further insight into the structure of the solvent-inserted boronate esters, showing that the inserted solvent has its hydrogen primarily on the amine. Lastly, studies of the use of boronate esters as receptors for simple alcohols and carboxylic acids are described.