2,4,6-tris-(4-vinylphenyl)cyclotriboroxane | 16396-62-6

• 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: 2,4,6-tris-(4-vinylphenyl)cyclotriboroxane
• 英文别名: tris(4-vinylpheny1)boroxine；tri(4-vinylphenyl)boroxine；tris(4-vinylphenyl)boroxine；Tris-<4-vinyl-phenyl>-boroxin；Tri-(p-styryl)-boroxine；<4-Vinyl-phenyl>-boroxol；tris-(4-vinyl-phenyl)-cyclotriboroxane；Tris-(4-vinyl-phenyl)-boroxin；tris(p-vinylphenyl)boroxine；p-Vinyl-benzol-boranhydrid；2,4,6-Tris(4-ethenylphenyl)-1,3,5,2,4,6-trioxatriborinane
• CAS: 16396-62-6
• 化学式: C₂₄H₂₁B₃O₃
• 分子量: 389.862
• InChiKey: JTGSJFSOAAJGPP-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C(Solv: toluene (108-88-3))
• 沸点：
  468.9±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘化氰 、 2,4,6-tris-(4-vinylphenyl)cyclotriboroxane 在 (CuOTf)*toluene 、 cesium fluoride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以71%的产率得到4-氰基苯乙烯
  参考文献：
  名称：

  Copper-Catalyzed Cyanation of Aryl- and Alkenylboronic Reagents with Cyanogen Iodide

  摘要：

  Direct catalytic cyanation of organoboronic acids with cyanogen iodide has been achieved by using a copper bipyridine catalyst system. The cyanation reaction is likely to occur through two catalytic cycles: copper(II)-catalyzed iodination of organoboronic acids and the following cyanidocopper(I)-mediated cyanation of organic iodides.

  DOI：

  10.1021/acs.orglett.5b01924
• 作为产物：
  描述：

  4-氯苯乙烯 在 magnesium 、 硼酸三丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到2,4,6-tris-(4-vinylphenyl)cyclotriboroxane
  参考文献：
  名称：

  Preparation of Organoboron Block Copolymers via ATRP of Silicon and Boron-Functionalized Monomers

  摘要：

  DOI：

  10.1021/ma051615p

文献信息

• Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Tertiary Sulfones
  作者：Zachary T. Ariki、Yuuki Maekawa、Masakazu Nambo、Cathleen M. Crudden

  DOI：10.1021/jacs.7b10855

  日期：2018.1.10

  benzylic and allylic sulfones with arylboroxines. A variety of tertiary sulfones, which can easily be prepared via a deprotonation-alkylation route, were reacted to afford symmetric and unsymmetric quaternary products in good yields. We highlight the use of either BrettPhos or Doyle's phosphines as effective ligands for these challenging desulfonative coupling reactions. The utility of this methodology

  我们描述了叔苄基和烯丙基砜与芳基环硼烷的镍催化 Suzuki-Miyaura 交叉偶联的开发。可以通过去质子化-烷基化路线轻松制备的各种叔砜反应以良好的收率提供对称和不对称季产物。我们强调使用 BrettPhos 或 Doyle 膦作为这些具有挑战性的脱磺化偶联反应的有效配体。这种方法的实用性在维生素 D 受体调节剂类似物的简明合成中得到了证明。
• [EN] SYNTHESIS AND USE OF FLUORINATED COMPOUNDS<br/>[FR] SYNTHÈSE ET UTILISATION DE COMPOSÉS FLUORÉS
  申请人：UNIV PENNSYLVANIA

  公开号：WO2014126990A1

  公开（公告）日：2014-08-21

  The invention is directed to the preparation of fluorinated compounds and their use in organic synthesis. In particular, the invention is directed to methods of reacting compounds of structure with Rf-CH=N2 or (CF3)2C=N2 to form a perfluoroalkylate or -arylated compounds, and products derived from these reactions, where X, YB, and Rf are described herein.

  本发明涉及氟化化合物的制备及其在有机合成中的用途。特别是，本发明涉及将结构式化合物与Rf-CH=N2或(CF3)2C=N2反应以形成全氟烷基或芳基化合物的 methods，以及由此反应得到的产品，其中X，YB和Rf如本文所述。
• Molecular design of novel transition state analogues for molecular imprinting
  作者：Biffis、Wulff

  DOI：10.1039/b102500g

  日期：2001.12.3

  The synthesis and characterisation of novel polymerisable heterocycles containing boron is described. The compounds were designed to serve as transition state analogues of the enantioselective borane reduction of prochiral ketones with oxazaborolidine catalysts (CBS reduction). Preliminary results show that the heterocycles can be conveniently used as template monomers in the synthesis of molecularly imprinted polymers.

  关于含硼新型可聚合杂环化合物的合成和表征，本文进行了详细描述。这些化合物旨在作为手性硼烷对非手性酮进行选择性还原的过渡态类似物，该过程采用噁唑硼啉（CBS）催化剂（即CBS还原反应）。初步研究结果显示，这些杂环化合物可以方便地用作分子印迹聚合物合成的模板单体。
• Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids
  作者：Claudio Bomio、Mikhail A. Kabeshov、Arthur R. Lit、Shing-Hing Lau、Janna Ehlert、Claudio Battilocchio、Steven V. Ley

  DOI：10.1039/c7sc02264f

  日期：——

  By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.

  通过计算和实验机理的研究，阐明了硼氧化合物在重氮化合物与硼酸之间的反应中的基本作用。因此，开发了使用TMSCHN2选择性地进行芳烃和乙烯基硼氧烷的无金属碳-碳同系物反应，从而获得了TMS-频哪醇硼酸酯产品。
• Diastereoselective Synthesis of Vicinally Bis(trifluoromethylated) Alkylboron Compounds through Successive Insertions of 2,2,2-Trifluorodiazoethane
  作者：Gary A. Molander、DaWeon Ryu

  DOI：10.1002/anie.201408191

  日期：2014.12.15

  development of diverse methods for incorporating this functional group. A recently reported route to α‐trifluoromethylated alkylboron compounds by an α‐transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the CB bond into other functional

  嵌入的CF 3取代基在有机亚结构内的有用性，需要开发各种方法来引入该官能团。最近报道的一种通过α-转移机制合成α-三氟甲基化烷基硼化合物的途径现已扩展到以非对映选择性的方式合成前所未有的，毒的二三氟甲基化烷基硼化合物。这些产品的实用性通过将CB键转换为其他官能团来突出。