o-boronobenzalmethoxyamine | 160161-70-6

• 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: o-boronobenzalmethoxyamine
• 英文别名: [2-[(E)-methoxyiminomethyl]phenyl]boronic acid
• CAS: 160161-70-6
• 化学式: C₈H₁₀BNO₃
• 分子量: 178.983
• InChiKey: PNGJLBYHEFMHCA-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  o-boronobenzalmethoxyamine 、 邻苯二酚 以 苯 为溶剂， 以75%的产率得到o-boronobenzalmethoxyamine catechol ester
  参考文献：
  名称：

  Synthesis and X-ray crystal structure investigation of a potential boronate affinity chromatography ligando-boronobenzalmethoxyamine

  摘要：

  A potential boronate affinity chromatography ligand o-boronobenzalmethoxyamine (IV) and its precursor [o-formylbenzeneboronic acid (III)] were synthesized and characterized by three-dimensional single-crystal X-ray diffractometry. Both compounds contained no bonding between the boron atoms and the oxygen atoms [O(3)] of the distinguishing functional group. In addition, B-11 NMR data confirmed the lack of any coordination between the boron and oxygen atoms in the boronic acid compounds III and IV and the catachol ester derivative (V) of IV. o-Formylbenzeneboronic acid (III) crystallizes in space group P2(1)/n with a = 3.883(1), b = 13.225(1), c = 14.029(2)Angstrom, beta = 92.16(1)degrees, and four molecules per unit cell. o-Boronobenzalmethoxyamine (IV) crystallizes in space group Pccn with a = 14.158(2), b = 17.156(1), c = 7.734(2)Angstrom, and eight molecules per unit cell. Selected bend distances and angles are tabularized.

  DOI：

  10.1007/bf01671677
• 作为产物：
  描述：

  o-tolueneboronic anhydride 在 bromine 、 NaOH 作用下， 以 四氯化碳 、 水 为溶剂， 生成 o-boronobenzalmethoxyamine
  参考文献：
  名称：

  Synthesis and X-ray crystal structure investigation of a potential boronate affinity chromatography ligando-boronobenzalmethoxyamine

  摘要：

  A potential boronate affinity chromatography ligand o-boronobenzalmethoxyamine (IV) and its precursor [o-formylbenzeneboronic acid (III)] were synthesized and characterized by three-dimensional single-crystal X-ray diffractometry. Both compounds contained no bonding between the boron atoms and the oxygen atoms [O(3)] of the distinguishing functional group. In addition, B-11 NMR data confirmed the lack of any coordination between the boron and oxygen atoms in the boronic acid compounds III and IV and the catachol ester derivative (V) of IV. o-Formylbenzeneboronic acid (III) crystallizes in space group P2(1)/n with a = 3.883(1), b = 13.225(1), c = 14.029(2)Angstrom, beta = 92.16(1)degrees, and four molecules per unit cell. o-Boronobenzalmethoxyamine (IV) crystallizes in space group Pccn with a = 14.158(2), b = 17.156(1), c = 7.734(2)Angstrom, and eight molecules per unit cell. Selected bend distances and angles are tabularized.

  DOI：

  10.1007/bf01671677

文献信息

• Diazaborines oxidize slowly with H₂O₂ but rapidly with peroxynitrite in aqueous buffer
  作者：Jack G. Haggett、Gun Su Han、Angela R. Moser、Julian V. A. Golzwarden、Shubham Vyas、Dylan W. Domaille

  DOI：10.1039/d1ob01668g

  日期：——

  Reactive oxygen species (ROS) such as hydrogen peroxide (H2O2) and peroxynitrite (ONOO−) oxidize arylboronic acids to their corresponding phenols. When used in molecular imaging probes and in ROS-responsive molecules, however, simple arylboronic acids struggle to discriminate between H2O2 and ONOO− because of their fast rate of reaction with both ROS. Here, we show that diazaborines (DABs) react slowly

  过氧化氢 (H 2 O 2 ) 和过氧亚硝酸盐 (ONOO - )等活性氧 (ROS) 可将芳基硼酸氧化为相应的酚类。然而，当用于分子成像探针和 ROS 响应分子时，简单的芳基硼酸很难区分 H 2 O 2和 ONOO -因为它们与两种 ROS 反应速度快。在这里，我们显示二氮杂硼烷 (DAB) 与 H 2 O 2反应缓慢，但在水性缓冲液中与过氧亚硝酸盐反应迅速。除了它们与 H 2 O 2的缓慢反应外，DAB 与 H 2氧化的直接产物O 2和ONOO -可以产生动力学捕获的C N Z -异构体，其与其E -异构体缓慢平衡。总之，我们的工作表明，与芳基硼酸相比，二氮硼烷在 H 2 O 2和 ONOO之间表现出更强的动力学区分，为化学生物学中基于二氮硼烷的工具开辟了新的机会。