1,4-bis((Z)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl)benzene | 1192488-89-3

• 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: 1,4-bis((Z)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl)benzene
• 英文别名: 1,4-bis[(Z)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl]benzene
• CAS: 1192488-89-3
• 化学式: C₂₂H₃₂B₂O₄
• 分子量: 382.116
• InChiKey: IPLBOIYJNOXPAD-VMNXYWKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 1,4-bis[(Z)-2-(butyltelluro)vinyl]benzene 在 正丁基锂 作用下， 以 hexanes 、 乙醚 为溶剂， 以22%的产率得到1,4-bis((Z)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl)benzene
  参考文献：
  名称：

  Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

  摘要：

  A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4) (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.06.092

文献信息

• 一种烯基硼酸酯及其制备方法和应用
  申请人：中山大学

  公开号：CN116396313A

  公开（公告）日：2023-07-07

  本发明公开了一种烯基硼酸酯及其制备方法和应用，烯基硼酸酯的制备方法包括如下步骤：惰性氛围中，式(I)化合物在钴催化剂、配体、硼试剂和碱作用下反应得式(II)化合物所述配体包括阳离子和阴离子，所述配体的阳离子如式(Ⅲ)所示：该方法采用钴催化剂对炔烃进行催化硼氢化，钴催化剂廉价易得、环境友好，避免了有毒、昂贵的重金属催化剂的使用，开发了廉价易得、环境友好的催化剂；同时该方法适用于各种类型的炔烃，底物适用范围广，能够实现各种类型炔烃发生高效、高选择性的硼氢化反应；该方法可以进行较大规模的烯基硼酸酯的制备，进行放大试验时不会出现产率明显下降的问题。
• Ruthenium Catalyzed Hydroboration of Terminal Alkynes to <i>Z</i>-Vinylboronates
  作者：Chidambaram Gunanathan、Markus Hölscher、Fangfang Pan、Walter Leitner

  DOI：10.1021/ja307233p

  日期：2012.9.5

  The nonclassical ruthenium hydride pincer complex [Ru(PNP)(H)(2)(H-2)] 1 (PNP = 1,3-bis(di-tert-butyl-phosphinomethyl)pyridine) catalyzes the anti-Markovnikov addition of pinacolborane to terminal alkynes yielding Z-vinylboronates at mild conditions. The complex [Ru(PNP)(H)(2)(HBpin)] 2 (HBpin = pinacolborane), which was identified at the end of the reaction and prepared independently, is proposed as the direct precursor to the catalytic cycle involving rearrangement of coordinated alkyne to Z-vinylidene as a key step for the apparent trans-hydroboration.