1-hydro-2-vinyl-1,2-azaborinine | 1153686-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-hydro-2-vinyl-1,2-azaborinine
• 英文别名: 1,2-dihydro-2-vinyl-1,2-azaborine；C4H4NHBvinyl；2-ethenyl-1H-azaborinine
• CAS: 1153686-52-2
• 化学式: C₆H₈BN
• 分子量: 104.947
• InChiKey: CZBUTCWAVGQDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hydro-2-vinyl-1,2-azaborinine 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 11.0h， 以63%的产率得到1,2-dihydro-2-vinyl-1,2-azaborine-1-yllithium
  参考文献：
  名称：

  The ligand properties of 2-vinyl-1,2-azaboratabenzene

  摘要：

  Lithium 2-vinyl-1,2-azaboratabenzene 1b has been prepared by a multistep synthesis from 2,2-dibutyl-2,5-dihydro-1-trimethylsilyl-1H-1,2-azastannole 6. The reaction of 1b with one equivalent of [Cp*RuCl](4) gave the very labile sandwich compound 11. However, the reaction of 1b with 2 equiv. of [Cp*RuCl](4) afforded the stable diruthenium complex 12. The X-ray structure of 12 shows that the first Cp*Ru moiety is pi-bound to the 1,2-azaboratabenzene ring while the second is bound to Cl and to the nitrogen and the pendant B-vinyl of the 1,2-azaboratabenzene group. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.10.043
• 作为产物：
  描述：

  1,2-dihydro-1-trimethylsilyl-2-vinyl-1,2-azaborine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-hydro-2-vinyl-1,2-azaborinine
  参考文献：
  名称：

  BN聚苯乙烯：新兴的光学材料和多功能中间体

  摘要：

  BN聚苯乙烯是一类新兴的用芳香族侧链官能化的聚烯烃，其中至少一个CC键被BN键取代。这类结构相对于有机聚合物表现出不同寻常的光物理性质。BN聚苯乙烯在制备功能性聚合物（包括立构规整的极性聚烯烃）中用作中间体。强调了BN对CC键取代反应性和性能的影响。

  DOI：

  10.1021/acs.joc.8b02921

文献信息

• Nucleophilic Aromatic Substitution Reactions of 1,2-Dihydro-1,2-Azaborine
  作者：Ashley N. Lamm、Edward B. Garner、David A. Dixon、Shih-Yuan Liu

  DOI：10.1002/anie.201103192

  日期：2011.8.22

  Could go either way: The addition of nucleophiles to the parent 1,2‐dihydro‐1,2‐azaborine and subsequent quenching with an electrophile generates novel substituted 1,2‐azaborine derivatives (see scheme). Mechanistic studies are consistent with two distinct nucleophilic aromatic substitution pathways depending on the nature of the nucleophile.

  可以采用任何一种方式：将亲核试剂添加到母体 1,2-dihydro-1,2-azaborine 上，随后用亲电子试剂淬灭，生成新的取代的 1,2-azaborine 衍生物（参见方案）。根据亲核试剂的性质，机理研究与两种不同的亲核芳香取代途径一致。
• Synthesis by free radical polymerization and properties of BN-polystyrene and BN-poly(vinylbiphenyl)
  作者：Wen-Ming Wan、Andrew W. Baggett、Fei Cheng、Huina Lin、Shih-Yuan Liu、Frieder Jäkle

  DOI：10.1039/c6cc07332h

  日期：——

  Free radical polymerization of B-vinyl- and B-styryl-functionalized azaborinine monomers gives organic-inorganic hybrid polymers with distinctly different materials properties compared to the corresponding carbonaceous polystyrene derivatives.

  与相应的碳质聚苯乙烯衍生物相比，B-乙烯基和B-苯乙烯基官能化的氮杂硼丙氨酸单体的自由基聚合可提供具有明显不同的材料性能的有机-无机杂化聚合物。
• Protecting Group-Free Synthesis of 1,2-Azaborines: A Simple Approach to the Construction of BN-Benzenoids
  作者：Eric R. Abbey、Ashley N. Lamm、Andrew W. Baggett、Lev N. Zakharov、Shih-Yuan Liu

  DOI：10.1021/ja4073436

  日期：2013.8.28

  The protecting group-free synthesis of a versatile 1,2-azaborine synthon 5 is described. Previously inaccessible 1,2-azaborine derivatives, including the BN isostere of phenyl phenylacetate and BN1 triphenylmethane were prepared from 5 and characterized. The structural investigation of BN phenyl phenylacetate revealed the presence of a unique NH-carbonyl hydrogen bond that is not present in the corresponding carbonaceous analogue. The methyne CH in BN triphenylmethane was found to be less acidic than the corresponding proton in triphenylmethane. The gram-quantity synthesis of the parent 1,2-azaborine 4 was demonstrated, which enabled the characterization of its boiling point, density, refractive index, and its polarity on the E-T(30) scale.
• BN Polystyrenes: Emerging Optical Materials and Versatile Intermediates
  作者：Heidi L. van de Wouw、Rebekka S. Klausen

  DOI：10.1021/acs.joc.8b02921

  日期：2019.2.1

  at least one CC bond is replaced with a BN bond. This class of structures exhibits unusual photophysical properties relative to organic polymers. BN polystyrenes serve as intermediates in the preparation of functional polymers, including stereoregular polar polyolefins. The consequences of BN for CC bond substitution on reactivity and properties are highlighted.

  BN聚苯乙烯是一类新兴的用芳香族侧链官能化的聚烯烃，其中至少一个CC键被BN键取代。这类结构相对于有机聚合物表现出不同寻常的光物理性质。BN聚苯乙烯在制备功能性聚合物（包括立构规整的极性聚烯烃）中用作中间体。强调了BN对CC键取代反应性和性能的影响。
• The ligand properties of 2-vinyl-1,2-azaboratabenzene
  作者：Jun Pan、Jeff W. Kampf、Arthur J. Ashe

  DOI：10.1016/j.jorganchem.2008.10.043

  日期：2009.4

  Lithium 2-vinyl-1,2-azaboratabenzene 1b has been prepared by a multistep synthesis from 2,2-dibutyl-2,5-dihydro-1-trimethylsilyl-1H-1,2-azastannole 6. The reaction of 1b with one equivalent of [Cp*RuCl](4) gave the very labile sandwich compound 11. However, the reaction of 1b with 2 equiv. of [Cp*RuCl](4) afforded the stable diruthenium complex 12. The X-ray structure of 12 shows that the first Cp*Ru moiety is pi-bound to the 1,2-azaboratabenzene ring while the second is bound to Cl and to the nitrogen and the pendant B-vinyl of the 1,2-azaboratabenzene group. (C) 2008 Elsevier B.V. All rights reserved.