1H-benzo[d][1,2,6]oxazaborinin-1-ol | 17067-02-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1H-benzo[d][1,2,6]oxazaborinin-1-ol
• 英文别名: 4-Hydroxy-4,3-boroxaro-isochinolin；1H-2,3,1-Benzoxazaborinin-1-ol；1-hydroxy-2,3,1-benzoxazaborinine
• CAS: 17067-02-6
• 化学式: C₇H₆BNO₂
• 分子量: 146.941
• InChiKey: LHYFQSZSVODPSE-UHFFFAOYSA-N

物化性质

• 沸点：
  291.3±23.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-benzo[d][1,2,6]oxazaborinin-1-ol 以 not given 为溶剂， 生成
  参考文献：
  名称：

  Planar Boron Heterocycles with Nucleic Acid-Like Hydrogen-Bonding Motifs

  摘要：

  To promote the development of boron-containing purine analogues that exist in planar, non-zwitterionic dominant structural form in aqueous solution, rigorous solution and solid state structural analyses of 1-hydroxy-1H-2,3,1-benzoxazaborine (1), 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine (2), and related 2,3,1-benzodiheteraborines were undertaken. With the aid of isotope-enriched compounds, a multisolvent H-1, C-13, B-11, and N-15 NMR spectroscopic analysis of 1 and 2 was conducted, providing structurally-diagnostic chemical shift data for all non-oxygen atoms that constitute their heterocyclic peripheries. In addition, single-crystal X-ray diffraction analyses of 1 and 2 were performed. In stark contrast to their 2,4,1 isomeric counterparts, the 2,3,1-benzoxaza- and benzodiazaborines exist in planar structural form in protic solution and in the solid state and display proton dissociative and associative tendencies reflective of the predominant Bronsted, yet still Lewis acidic-capable character of the B-OH group together with the basic one at the C4-N3 imine group. In the solid state, 1 and 2 display intermolecular hydrogen-bonding patterns not too dissimilar from the motifs of certain natural nucleic acid bases. Diazaborine 2 was shown by VT-NMR to undergo a triple hydrogen-bonding solution association with a 2',3',5'-tri-O-protected cytidine in a demonstration of one biomimetic potential held by a 1-hydroxy-2,3,1-diheteraborine periphery. In general, 1, 2, and related 1-hydroxy-2,3,1-benzodiheteraborine heterocycles were found to be characterized by an environment-dependent O1-->N3 Bronsted prototropy and B-OH group Bronsted/Lewis acid ambidency so sensitive and subtle that certain past difficulties encountered in attempts to delineate their physicochemical properties now become readily appreciated.

  DOI：

  10.1021/ja963784i
• 作为产物：
  描述：

  (2-Br2CHC6H4)B(OH)2 在 氢氧化钾 、 羟胺 作用下， 生成 1H-benzo[d][1,2,6]oxazaborinin-1-ol
  参考文献：
  名称：

  Synthesis of Aromatic Boronic Acids. Aldehydo Boronic Acids and a Boronic Acid Analog of Tyrosine¹

  摘要：

  DOI：

  10.1021/ja01537a021

文献信息

• Lewis or Brønsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles
  作者：M. Zain H. Kazmi、Jason P. G. Rygus、Hwee Ting Ang、Marco Paladino、Matthew A. Johnson、Michael J. Ferguson、Dennis G. Hall

  DOI：10.1021/jacs.1c02462

  日期：2021.7.14

  hemiboronic acids may possess sufficient aromatic character to act as Brønsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic “naphthoid” isosteres. Here

  含硼杂环在从药物发现到材料科学的各种应用中都很重要；因此，为了优化这些功能，需要清楚地了解它们的结构和反应性。尽管硼酸的硼醇 (B-OH) 单元表现为路易斯酸以形成四价三羟基硼酸盐共轭碱，但有人提出假芳族半硼酸可能具有足够的芳香性以充当布朗斯台德酸并形成硼氧共轭碱，从而避免了四价硼酸阴离子会发生的环芳香性的破坏。到目前为止，还没有确凿的证据来确定共轭碱的结构和半硼“萘酚”等排体的含硼环的芳香特性。这里，这些问题通过对一系列模型苯并二氮杂硼和苯并二氮杂硼萘烷类化合物的实验、光谱、X 射线晶体学和计算研究相结合来解决。尽管这些半硼杂环明确显示在水溶液中表现为路易斯酸，但硼氮杂环衍生物具有部分芳香性，前提是它们的氮孤电子对足以参与扩展的离域化。正如动态交换和交叉实验所证明的那样，这些杂环在中性水性介质中是稳定的，并且它们的测量 p 尽管这些半硼杂环明确显示在水溶液中表现为路易斯酸，但硼氮杂环衍生
• Expanding the Role of Boron in New Drug Chemotypes: Properties, Chemistry, Pharmaceutical Potential of Hemiboronic Naphthoids
  作者：M. Zain H. Kazmi、Olivia M. Schneider、Dennis G. Hall

  DOI：10.1021/acs.jmedchem.3c01194

  日期：2023.10.12

  (Candida albicans) and antibacterial activity (MRSA, Escherichia coli), unveiling promising benzoxazaborines with low micromolar minimum inhibitory concentration values. Select DMPK assays of representative compounds suggest promising drug-like behavior for all four subclasses. Moreover, several drug isosteres were evaluated for anti-inflammatory and anticancer activity as appropriate.

  新的化学型和生物等排体可以在药物发现中开辟新的化学空间，并有助于满足对抗感染和其他疾病的新型药物的迫切需求。为了确定新的含硼药物化学型，本文详细介绍了拟芳香族半硼萘类、苯并恶氮杂硼烷和苯并二氮杂硼烷的综合评价。确定了四个亚类原型成员在水介质中的相关物理性质（酸度、溶解度、log P和稳定性）。这两种支架都适合药物发现中使用的常见反应，例如化学选择性 Suzuki-Miyaura、Chan-Lam 和酰胺化反应。准备了小型模型库来评估这些转化的范围，并对整个集合进行了抗真菌（白色念珠菌）和抗菌活性（MRSA、大肠杆菌）筛选，揭示了具有低微摩尔最低抑制浓度值的有前景的苯并恶唑硼烷。选择代表性化合物的 DMPK 检测表明所有四个亚类都具有良好的药物样行为。此外，还适当评估了几种药物电子等排体的抗炎和抗癌活性。
• New Heteroaromatic Compounds. XX.¹ Derivatives of 4,3-Borazaroisoquinoline²
  作者：Michael J. S. Dewar、Ralph C. Dougherty

  DOI：10.1021/ja01057a028

  日期：1964.2
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.8, 9, page 141 - 149
  作者：

  DOI：——

  日期：——
• Arylboronic acids. Imino derivatives from O-formylbenzeneboronic acid
  作者：Howard E. Dunn、Joseph C. Catlin、Harold R. Snyder

  DOI：10.1021/jo01276a040

  日期：1968.12