benzo[d][1,2,3]diazaborinin-1(2H)-ol | 17091-90-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: benzo[d][1,2,3]diazaborinin-1(2H)-ol
• 英文别名: 4-Hydroxy-4,3-borazaro-isochinolin；2,3,1-Benzodiazaborinin-1(2H)-ol；1-hydroxy-2H-2,3,1-benzodiazaborinine
• CAS: 17091-90-6
• 化学式: C₇H₇BN₂O
• 分子量: 145.956
• InChiKey: VYLMBCVKHNTBIA-UHFFFAOYSA-N

物化性质

• 沸点：
  314.4±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 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：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[d][1,2,3]diazaborinin-1(2H)-ol 、 重氧水 以 乙腈 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：

  (5-氟-2-甲酰基苯基)硼酸 以 甲醇 、 乙醇 为溶剂， 反应 28.0h， 生成 benzo[d][1,2,3]diazaborinin-1(2H)-ol
  参考文献：
  名称：

  刘易斯还是布朗斯特？含硼醇的萘杂环化合物的酸性和芳香性的精馏

  摘要：

  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

  DOI：

  10.1021/jacs.1c02462

文献信息

• [EN] BORON CONTAINING COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS CONTENANT DU BORE ET LEURS UTILISATIONS
  申请人：5METIS INC

  公开号：WO2022040157A1

  公开（公告）日：2022-02-24

  The present disclosure relates to novel boron-containing compounds and their novel uses, e.g., as active ingredients that have pesticidal activity. The disclosure also relates to agrochemical compositions and their use in agriculture or horticulture for the control or prevention of infestation of plants, plant parts, plant propagation materials, harvested food crops, or seeds by pests, specifically fungi and nematodes. The disclosure further relates to methods for promoting plant performance and/or curatively or preventively controlling phytopathogens, (particularly fungi and nematodes) on or in a plant, plant parts, plant propagation materials, seeds, harvested fruits, or vegetables.

  本公开涉及新型含硼化合物及其新用途，例如作为具有杀虫活性的活性成分。该公开还涉及农药组合物及其在农业或园艺中用于控制或预防植物、植物部分、植物繁殖材料、收获的食物作物或种子受到害虫（特别是真菌和线虫）侵害的用途。该公开还涉及促进植物生长表现和/或在植物、植物部分、植物繁殖材料、种子、收获的水果或蔬菜上或内部治疗或预防控制植物病原体（特别是真菌和线虫）的方法。
• 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
• Planar Boron Heterocycles with Nucleic Acid-Like Hydrogen-Bonding Motifs
  作者：Michael P. Groziak、Liya Chen、Lin Yi、Paul D. Robinson

  DOI：10.1021/ja963784i

  日期：1997.8.1

  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.