2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one | 28249-75-4

• 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-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
• 英文别名: 2-Phenyl-1,3-dihydro-1,3,2-benzodiazaborinin-4-one
• CAS: 28249-75-4
• 化学式: C₁₃H₁₁BN₂O
• 分子量: 222.054
• InChiKey: PDCUEAHXLWTCAA-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 在 盐酸 、 RuH₂(CO)(PPh₃)₃ 、 norbornene 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 51.0h， 生成 2,4,6-tris[2-(dimethylphenylsilyl)phenyl]boroxine
  参考文献：
  名称：

  Anthranilamide: A Simple, Removable ortho-Directing Modifier for Arylboronic Acids Serving also as a Protecting Group in Cross-Coupling Reactions

  摘要：

  Anthranilamide (AAM) serves as a bifunctional modifier on the boron atom in catalytic transformations of arylboronic acids. It makes boronyl groups unreactive in Suzuki-Miyaura coupling and promotes Ru-catalyzed ortho-silylation. Suzuki-Miyaura coupling of AAM-modified bromophenylboronic acids with tolylboronic acid gave 1,1'-biaryl-4-boronic acid bearing AAM on the boron atom, which subsequently underwent Ru-catalyzed ortho-silylation at the 3-position by virtue of the ortho-directing effect of the AAM group.

  DOI：

  10.1021/ol200764g
• 作为产物：
  描述：

  苯硼酸酐 在 amine 作用下， 生成 2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.9, 5.2.4, page 189 - 199

  摘要：

  DOI：

文献信息

• Chemoselective <i>N</i>-arylation of aminobenzamides <i>via</i> copper catalysed Chan–Evans–Lam reactions
  作者：Shuai Liu、Weisai Zu、Jinli Zhang、Liang Xu

  DOI：10.1039/c7ob02491f

  日期：——

  Chemoselective N-arylation of unprotected aminobenzamides was achieved via Cu-catalysed Chan–Evans–Lam cross-coupling with aryl boronic acids for the first time. Simple copper catalysts enable the selective arylation of amino groups in ortho/meta/para-aminobenzamides under open-flask conditions. The reactions were scalable and compatible with a wide range of functional groups.

  未保护的氨基苯甲酰胺的化学选择性N-芳基化是通过Cu催化的Chan-Evans-Lam与芳基硼酸的首次交叉偶联而实现的。简单的铜催化剂可以在开瓶条件下使邻/间/对-氨基苯甲酰胺中的氨基选择性芳基化。反应是可扩展的，并且与多种官能团相容。
• An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2‐Benzodiazaborininones from Boronic Acids and Anthranilamides
  作者：Hao‐Jie Wang、Mo Zhang、Wen‐Jing Li、Yu Ni、Jin Lin、Zhan‐Hui Zhang

  DOI：10.1002/adsc.201900827

  日期：2019.11.5

  An efficient Ni/Pd catalyzed chemoselective synthesis of 1,3,2‐benzodiazaborininones from boronic acids and anthranilamide has been developed. This protocol allows for the rapid and straightforward access to a wide range of 1,3,2‐benzodiazaborininones at roomtemperature with excellent functional group tolerance.

  已经开发了一种高效的Ni / Pd催化从硼酸和邻氨基苯甲酰胺化学合成1,3,2-苯并二氮杂硼杂环丁烷酮的方法。该协议允许在室温下快速，直接地获得具有出色的官能团耐受性的各种1,3,2-苯并二氮杂硼硼烷酮。
• A General Method for Interconversion of Boronic Acid Protecting Groups: Trifluoroborates as Common Intermediates
  作者：Quentin I. Churches、Joel F. Hooper、Craig A. Hutton

  DOI：10.1021/acs.joc.5b00182

  日期：2015.6.5

  interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables

  我们已经开发了通过中间有机三氟硼酸酯相互转化各种受保护的硼酸的通用协议。迄今为止已经耐直接转化成三氟硼酸酯的N-甲基亚氨基二乙酰基硼酸酯已经显示出在高温下发生氟化分解。在三甲基甲硅烷基氯和各种双亲核试剂的存在下，有机三氟硼酸酯的随后溶剂分解能够生成多种受保护的硼酸。
• Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines
  作者：Geraint H. M. Davies、Asma Mukhtar、Borna Saeednia、Fatemeh Sherafat、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.joc.7b00747

  日期：2017.5.19

  boronic acids is described. An inexpensive, common reagent, SiO2, was found to serve as both a fluorophile and desiccant to facilitate the annulation process across three different azaborininone platforms. Computational analysis of some of the cores synthesized in this study was undertaken to compare the azaborininones with the analogous carbon-based heterocyclic systems. Computationally derived pKa values

  描述了一种使用简单的试剂和条件从有机三氟硼酸盐和硼酸两者中获得氮杂硼杂环丁酮（含羰基的硼基杂环支架）的方法。发现便宜的普通试剂SiO2既可以用作亲氟剂也可以用作干燥剂，以促进跨三个不同的氮杂硼氢化萘酮平台的成环过程。对本研究中合成的某些核进行了计算分析，以比较氮杂硼硼烷酮与类似的基于碳的杂环系统。通过计算得出的pKa值，NICS芳香度计算和静电势表面揭示了这些氮杂硼烷与它们的碳等排物之间独特的等电/同构关系，该关系根据硼的连通性而变化。
• Biological evaluation the 2‐aryl‐2,3‐dihydrobenzodiazaborinin‐4(1 <i>H</i> )‐ones as potential dual α‐glucosidase and α‐amylase inhibitors with antioxidant properties
  作者：Malose J. Mphahlele、Nontokozo M. Magwaza、Sibusiso T. Malindisa、Yee Siew Choong

  DOI：10.1111/cbdd.13893

  日期：2021.8

  through kinetics (in vitro) and molecular docking (in silico) studies. The test compounds also exhibited significant antioxidant activity through the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (NO) free radical scavenging assays. These azaborininone derivatives exhibited no effect on the viability of the human lung cancer (A549) cell line after 24 hr and were also not toxic towards the Vero

  2-aryl-2,3-dihydrobenzodiazaborinin-4(1 H)-ones (azaborinone) 合成为 2-arylquinazoline-4-ones 的类似物，并通过体外酶促测定筛选对 α-葡萄糖苷酶和 α-淀粉酶活性的抑制作用。与用作参考标准的阿卡波糖相比，这些氮杂硼烷酮对这些酶表现出中等至良好的抑制作用。结果通过动力学（体外）和分子对接（计算机）研究得到酶-配体相互作用的支持。测试化合物还通过 2,2-二苯基-1-苦基肼 (DPPH) 和一氧化氮 (NO) 自由基清除试验显示出显着的抗氧化活性。这些氮杂硼烷酮衍生物在 24 小时后对人肺癌 (A549) 细胞系的活力没有影响，并且对 Vero 细胞也没有毒性。