2-formylphenylboronic acid-¹⁰B | 269727-10-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 2-formylphenylboronic acid-¹⁰B
• 英文别名: (2-Formylphenyl)boronic-10B acid；(2-formylphenyl)(10B)boronic acid
• CAS: 269727-10-8
• 化学式: C₇H₇BO₃
• 分子量: 149.131
• InChiKey: DGUWACLYDSWXRZ-COJKEBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  、 2-formylphenylboronic acid-¹⁰B 、 、 在 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 生成 、 、
  参考文献：
  名称：

  Regiochemical Tagging:  A New Tool for Structural Characterization of Isomeric Components in Combinatorial Mixtures

  摘要：

  In this contribution we present a new combined synthetic and analytical strategy (regiochemical ragging) that allows facile determination of complete structure, including substituent position and regiochemistry, of mass-redundant components in complex combinatorial mixtures. The libraries of components (oxime ethers) are formed by the reaction of a mixture of substituents (aldehydes) with a scaffold containing several chemically similar attachment points (aminooxy groups), The structure of the resulting library components can then be determined from a combination of single MS and the tandem (MS/MS) spectra. Determination of the unique isomeric motif for each component is made possible via the following features of library design: (1) pan of the scafforld moiety, "transferable group" (the nitrogen atom from the oxime group) is transferred to the: substituent during fragmentation in the tandem experiment, (2) transferable groups on the scaffold differ from each other by either isotopic labels or fragmentation energies, and (3) mass-redundant substituents are isotopically labeled to create at least a 2 mass unit difference between them. The components of thr resulting library thus become labeled with different mass- and energy tags, which allows for precise regiochemical assignment of the functional group positions on the scaffold and substituents by mass spectrometry. The approach has been used to create and analyze a mixture of 27 isomeric compounds, each containing three boronic acid groups. The combination of the MS and MS/MS spectra of the tagged mixture has yielded a unique and structurally definitive signature of each component. Applications of the regiochemical tagging techniques to rapid synthesis and screening of combinatorial mixtures are discussed.

  DOI：

  10.1021/ja993844v
• 作为产物：
  描述：

  2-(2-溴苯基)-1,3-二恶烷 在 正丁基锂 、 三(甲氧基)硼烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 以55%的产率得到2-formylphenylboronic acid-¹⁰B
  参考文献：
  名称：

  Regiochemical Tagging:  A New Tool for Structural Characterization of Isomeric Components in Combinatorial Mixtures

  摘要：

  In this contribution we present a new combined synthetic and analytical strategy (regiochemical ragging) that allows facile determination of complete structure, including substituent position and regiochemistry, of mass-redundant components in complex combinatorial mixtures. The libraries of components (oxime ethers) are formed by the reaction of a mixture of substituents (aldehydes) with a scaffold containing several chemically similar attachment points (aminooxy groups), The structure of the resulting library components can then be determined from a combination of single MS and the tandem (MS/MS) spectra. Determination of the unique isomeric motif for each component is made possible via the following features of library design: (1) pan of the scafforld moiety, "transferable group" (the nitrogen atom from the oxime group) is transferred to the: substituent during fragmentation in the tandem experiment, (2) transferable groups on the scaffold differ from each other by either isotopic labels or fragmentation energies, and (3) mass-redundant substituents are isotopically labeled to create at least a 2 mass unit difference between them. The components of thr resulting library thus become labeled with different mass- and energy tags, which allows for precise regiochemical assignment of the functional group positions on the scaffold and substituents by mass spectrometry. The approach has been used to create and analyze a mixture of 27 isomeric compounds, each containing three boronic acid groups. The combination of the MS and MS/MS spectra of the tagged mixture has yielded a unique and structurally definitive signature of each component. Applications of the regiochemical tagging techniques to rapid synthesis and screening of combinatorial mixtures are discussed.

  DOI：

  10.1021/ja993844v

文献信息

• Conjugation of Phenylboronic Acid Moiety through Multistep Organic Transformations on Nanodiamond Surface for an Anticancer Nanodrug for Boron Neutron Capture Therapy
  作者：Masahiro Nishikawa、Heon Gyu Kang、Yajuan Zou、Hidekazu Takeuchi、Naoyoshi Matsuno、Minoru Suzuki、Naoki Komatsu

  DOI：10.1246/bcsj.20210200

  日期：2021.9.15

  in the field of nanomedicine due to its biocompatibility as well as various functionalities imparted by surface modification. Meanwhile, boron neutron capture therapy (BNCT) is an advanced cancer treatment utilizing nuclear fission reaction of 10B upon neutron irradiation. Recently, quite a few boron-containing nanoparticles have been investigated to deliver 10B atoms into cancer tissue selectively and

  爆炸纳米金刚石 (DND) 由于其生物相容性以及通过表面改性赋予的各种功能而引起了相当多的关注，特别是在纳米医学领域。同时，硼中子俘获疗法 (BNCT) 是一种利用10 B 在中子辐照时发生核裂变反应的晚期癌症治疗方法。最近，已经研究了相当多的含硼纳米粒子，以提供10B 原子选择性地和保留地进入癌组织。在这项研究中，我们探索了硼酸功能化的 DNDs 作为 BNCT 的抗癌剂。通过多步有机转化将苯硼酸 (PBA) 部分引入聚甘油 (PG) 改性的 DNDs (DND-PG)，给出硼原子的百分比顺序。通过简单的共价化学，该过程具有可扩展性和可靠性，并且所得产品分散良好，并且在生理条件下化学和物理稳定。在体内实验中，所得材料积累到肿瘤中，以在中子照射下发挥 BNCT 功效。这些结果表明，PBA 功能化的 DNDs 作为 BNCT 的抗癌纳米药物是有前景的候选者。
• Regiochemical Tagging:  A New Tool for Structural Characterization of Isomeric Components in Combinatorial Mixtures
  作者：Noureddin Nazarpack-Kandlousy、Igor V. Chernushevich、LingJie Meng、Ying Yang、Alexey V. Eliseev

  DOI：10.1021/ja993844v

  日期：2000.4.1

  In this contribution we present a new combined synthetic and analytical strategy (regiochemical ragging) that allows facile determination of complete structure, including substituent position and regiochemistry, of mass-redundant components in complex combinatorial mixtures. The libraries of components (oxime ethers) are formed by the reaction of a mixture of substituents (aldehydes) with a scaffold containing several chemically similar attachment points (aminooxy groups), The structure of the resulting library components can then be determined from a combination of single MS and the tandem (MS/MS) spectra. Determination of the unique isomeric motif for each component is made possible via the following features of library design: (1) pan of the scafforld moiety, "transferable group" (the nitrogen atom from the oxime group) is transferred to the: substituent during fragmentation in the tandem experiment, (2) transferable groups on the scaffold differ from each other by either isotopic labels or fragmentation energies, and (3) mass-redundant substituents are isotopically labeled to create at least a 2 mass unit difference between them. The components of thr resulting library thus become labeled with different mass- and energy tags, which allows for precise regiochemical assignment of the functional group positions on the scaffold and substituents by mass spectrometry. The approach has been used to create and analyze a mixture of 27 isomeric compounds, each containing three boronic acid groups. The combination of the MS and MS/MS spectra of the tagged mixture has yielded a unique and structurally definitive signature of each component. Applications of the regiochemical tagging techniques to rapid synthesis and screening of combinatorial mixtures are discussed.