bis(9-bora-10-oxa-phenanthrenyl)oxide | 15598-17-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: bis(9-bora-10-oxa-phenanthrenyl)oxide
• 英文别名: bis(boroxophenanthrenyl)ether；6H,6'H-6,6'-oxy-bis-dibenzo[c,e][1,2]oxaborinine；6H,6'H-6,6'-Oxy-bis-dibenz[c,e][1,2]oxaborinin；Bis-<10,9-boroxaro-phenanthryl-(10)>-ether；6,6'-oxybis(6H-dibenzo[c,e][1,2]oxaborinine)；6-benzo[c][1,2]benzoxaborinin-6-yloxybenzo[c][1,2]benzoxaborinine
• CAS: 15598-17-1
• 化学式: C₂₄H₁₆B₂O₃
• 分子量: 374.011
• InChiKey: IFUXSVCVJRHUGS-UHFFFAOYSA-N

物化性质

• 沸点：
  554.1±33.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• 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

• 作为产物：
  描述：

  邻苯基苯酚 在 三氯化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 bis(9-bora-10-oxa-phenanthrenyl)oxide
  参考文献：
  名称：

  Solid-state and solution phase reactivity of 10-hydroxy-10,9-boroxophenanthrene: a model building block for self-assembly processes

  摘要：

  通过实验和计算，发现 10-羟基-10,9-硼氧菲的相对稳定性及其亲电反应性与含硼杂环的部分芳香特性有关。介绍了 10-羟基-10,9-硼氧菲在固态下对其本身以及在溶液中对其他亲核物的亲电反应性。固态反应的机理已通过 X 射线衍射和热分析得到表征。不过，在溶液中，10-羟基-10,9-硼氧菲不会与自身发生反应，但它在溶液中会与苯甲醇迅速发生可逆反应，即使在低温下也是如此。这种选择性和可逆性反应非常适合用于自组装过程。

  DOI：

  10.1039/b110285k

文献信息

• Maringgele, W.; Meller, A.; Noltemeyer, M., Zeitschrift fur Anorganische und Allgemeine Chemie
  作者：Maringgele, W.、Meller, A.、Noltemeyer, M.、Sheldrick, G. M.

  DOI：——

  日期：——
• 269. New heteroaromatic compounds. Part V. Some 9,10-boroxarophenanthrenes
  作者：M. J. S. Dewar、R. Dietz

  DOI：10.1039/jr9600001344

  日期：——
• Aromatic boron-oxygen heterocycles
  作者：M.J.S. Dewar、R. Dietz

  DOI：10.1016/s0040-4039(01)99449-3

  日期：1959.1
• Detecting solid-state reactivity in 10-hydroxy-10,9-boroxophenanthrene using NMR spectroscopy
  作者：Diego Carnevale、Vicente del Amo、Douglas Philp、Sharon E. Ashbrook

  DOI：10.1016/j.tet.2010.05.065

  日期：2010.8

  Solid-state NMR spectroscopy and computational methods are used to probe the transformation of 10-hydroxy-10,9-boroxophenanthrene to its corresponding anhydride in the solid state. OFT calculations are used to assist the assignment of the NMR spectra of both these boron-containing heteroaromatic compounds, in solution and in the solid state. Solid-state NMR spectroscopy reveals that the dehydration of crystalline 10-hydroxy-10,9-boroxophenanthrene proceeds at relatively low temperatures a transformation, that is, undetectable by X-ray diffraction and gravimetric analysis. Computational methods are used to elucidate a plausible reaction pathway for this transformation and to explain its detection only by NMR methods. (C) 2010 Elsevier Ltd. All rights reserved.
• Solid-state and solution phase reactivity of 10-hydroxy-10,9-boroxophenanthrene: a model building block for self-assembly processes
  作者：Lyndsey M. Greig、Benson M. Kariuki、Scott Habershon、Neil Spencer、Roy L. Johnston、Kenneth D. M. Harris、Douglas Philp

  DOI：10.1039/b110285k

  日期：2002.6.7

  The relative stability of 10-hydroxy-10,9-boroxophenathrene and its electrophilic reactivity are traced through experiment and calculations to the partially aromatic character of the boron-containing heterocyclic ring. The electrophilic reactivity of 10-hydroxy-10,9-boroxophenathrene towards itself in the solid state and towards other nucleophiles in solution is described. The mechanism of the solid-state reaction has been characterised by both X-ray diffraction and thermal analysis. In solution, however, 10-hydroxy-10,9-boroxophenathrene does not react with itself, although it does react rapidly and reversibly with benzylic alcohols in solution, even at low temperatures. This selective and reversible reaction is ideal for use in self-assembly processes.

  通过实验和计算，发现 10-羟基-10,9-硼氧菲的相对稳定性及其亲电反应性与含硼杂环的部分芳香特性有关。介绍了 10-羟基-10,9-硼氧菲在固态下对其本身以及在溶液中对其他亲核物的亲电反应性。固态反应的机理已通过 X 射线衍射和热分析得到表征。不过，在溶液中，10-羟基-10,9-硼氧菲不会与自身发生反应，但它在溶液中会与苯甲醇迅速发生可逆反应，即使在低温下也是如此。这种选择性和可逆性反应非常适合用于自组装过程。