3-(2-azido-acetylamino)phenylboronic acid | 1392397-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2-azido-acetylamino)phenylboronic acid
• 英文别名: [3-[(2-Azidoacetyl)amino]phenyl]boronic acid；[3-[(2-azidoacetyl)amino]phenyl]boronic acid
• CAS: 1392397-13-5
• 化学式: C₈H₉BN₄O₃
• 分子量: 219.995
• InChiKey: TXYWNKZPALZDLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-2-methyl-N-(prop-2-ynyl)propanamide 、 3-(2-azido-acetylamino)phenylboronic acid 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以27%的产率得到
  参考文献：
  名称：

  Boronic Acid Terminated Thermo-Responsive and Fluorogenic Polymer: Controlling Polymer Architecture for Chemical Sensing and Affinity Separation

  摘要：

  Thermo-responsive poly(N-isopropylacrylamide) (polyNIPAm) containing terminal boronic acid was synthesized using atom transfer radical polymerization (ATRP) in combination with Cu(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reaction. Alkyne-terminated polyNIPAm was first synthesized by ATRP using an alkyne-containing initiator. A fluorogenic boronic acid, 3-(2-azido-acetylamino)phenylboronic acid (APBA) was then linked to the polyNIPArn through CuAAC. The synthesized polymers were characterized by H-1 NMR, FT-IR, UV-vis, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry, and turbidity measurements. The intensity of fluorescence emission of the boronic acid-terminated polyNIPAm (BA-polyNIPAm) was found to increase when increasing amount of a cis-diol compound (i.e., fructose) was added. At physiological pH value, the BA-polyNIPAm effectively bound fructose and could be easily separated from aqueous solution by raising the temperature above its lower critical solution temperature (LCST).

  DOI：

  10.1021/ma301213f

文献信息

• Boronic Acid Terminated Thermo-Responsive and Fluorogenic Polymer: Controlling Polymer Architecture for Chemical Sensing and Affinity Separation
  作者：Zhifeng Xu、Khan Mohammad Ahsan Uddin、Lei Ye

  DOI：10.1021/ma301213f

  日期：2012.8.28

  Thermo-responsive poly(N-isopropylacrylamide) (polyNIPAm) containing terminal boronic acid was synthesized using atom transfer radical polymerization (ATRP) in combination with Cu(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reaction. Alkyne-terminated polyNIPAm was first synthesized by ATRP using an alkyne-containing initiator. A fluorogenic boronic acid, 3-(2-azido-acetylamino)phenylboronic acid (APBA) was then linked to the polyNIPArn through CuAAC. The synthesized polymers were characterized by H-1 NMR, FT-IR, UV-vis, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry, and turbidity measurements. The intensity of fluorescence emission of the boronic acid-terminated polyNIPAm (BA-polyNIPAm) was found to increase when increasing amount of a cis-diol compound (i.e., fructose) was added. At physiological pH value, the BA-polyNIPAm effectively bound fructose and could be easily separated from aqueous solution by raising the temperature above its lower critical solution temperature (LCST).