9-蒽基硼酸二甲酯 | 1028205-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-蒽基硼酸二甲酯
• 英文名称: 9-anthryl(dimethoxy)borane
• 英文别名: 9-anthracenylboronic acid dimethyl ester；Anthracen-9-yl(dimethoxy)borane
• CAS: 1028205-77-7
• 化学式: C₁₆H₁₅BO₂
• 分子量: 250.105
• InChiKey: LPPLVNIVPDMIJR-UHFFFAOYSA-N

物化性质

• 熔点：
  81 °C(Solv: methanol (67-56-1))
• 沸点：
  405.9±14.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-蒽基硼酸二甲酯 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 四乙基氢氧化铵 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 2-(10-(benzo[a]anthracen-4-yl)anthracen-9-yl)-5-phenylpyrimidine
  参考文献：
  名称：

  MATERIALS FOR ORGANIC ELECTROLUMINESCENCE DEVICES

  摘要：

  这项发明涉及按照式(I)的嘧啶衍生物，以及包括所述嘧啶衍生物作为电子传输材料的有机电致发光器件。

  公开号：

  US20130032764A1
• 作为产物：
  描述：

  硼酸三甲酯 、 9-溴蒽 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 生成 9-蒽基硼酸二甲酯
  参考文献：
  名称：

  Supramolecular structures and spontaneous resolution: the case of ortho-substituted phenylboronic acids

  摘要：

  通过X射线衍射技术，确定了多种邻位取代的芳基硼酸的固态结构，包括邻溴苯基、邻苯基苯基、五甲基苯基和10-溴-9-蒽基。所有研究的硼酸在固态下均形成二聚体，但二聚体连接成链的方式与亲本苯硼酸有所不同。五甲基苯硼酸仅使用一个氢键，并通过额外的OH–π相互作用来连接二聚体，而其他所有研究的化合物则通过两个氢键将二聚体连接成链。10-溴-9-蒽基硼酸在结晶时发现自发分解其对映异构体形成一个外消旋混合物。

  DOI：

  10.1039/b719282g

文献信息

• Vaulted Biaryls in Catalysis: A Structure-Activity Relationship Guided Tour of the Immanent Domain of the VANOL Ligand
  作者：Yong Guan、Zhensheng Ding、William D. Wulff

  DOI：10.1002/chem.201302451

  日期：2013.11.11

  anion (boroxinate) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by H bonds to oxygen atoms O1–O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′‐ and

  BOROX 催化剂中的活性位点是一种手性多硼酸阴离子（硼酸），它由三当量的 B(OPh) 3和一个 VANOL 配体通过一分子底物原位组装而成。底物通过与氧原子 O1-O3 的 H 键与硼酸盐结合。在氮丙啶化反应中系统地研究了在 VANOL 配体的萘核的每个位置引入取代基的影响。4,4'-和8,8'-位的取代基对催化剂性能有负面影响，而7-和7'-位的取代基在正向影响最大。
• Synthesis and Optical Properties of Anthryl-substituted Tetracyclic Borepins
  作者：Yohei Adachi、Kohei Yamada、Joji Ohshita

  DOI：10.1246/cl.220139

  日期：2022.6.5

  Anthracene-substituted triarylboranes have been widely studied as optoelectronic materials because of their unique photophysical properties. In this work, we synthesized new anthryl-substituted boranes with a seven-membered aromatic ring system, so-called borepins. The anthryl-substituted tetracyclic borepins exhibited limited electronic interaction in the ground state, whereas their fluorescence spectra

  蒽取代的三芳基硼烷由于其独特的光物理性质而作为光电材料被广泛研究。在这项工作中，我们合成了具有七元芳环系统的新型蒽基取代硼烷，即所谓的硼烷。蒽基取代的四环borepins在基态下表现出有限的电子相互作用，而它们的荧光光谱与异丙叉基取代体系的荧光光谱明显不同。值得注意的是，当将氟化物添加到钻孔溶液中时，荧光增强，这归因于氟化物与硼中心的配位。
• Electronic Decoupling in Ground and Excited States of Asymmetric Biaryls
  作者：Martin Baumgarten、Lileta Gherghel、Jan Friedrich、Martin Jurczok、Wolfgang Rettig

  DOI：10.1021/jp9932315

  日期：2000.2.1

  New asymmetric biaryls have been synthesized in order to clarify the conditions necessary for charge-transfer transitions in photoexcited neutral compounds and biradical formation in doubly charged ground-state species. A parallel behavior for both types of approaches is observed and explained with a simple coupling model allowing prediction of the intermoiety coupling strength. It is shown that for weakly coupled biaryls the monoions are connected with charge localization and the dications and dianions form thermally excited biradicals while the fluorescence data indicate biradicaloid excited states connected with partial charge separation. More strongly coupled biaryls, on the other hand, result in diamagnetic species for the doubly charged ground-state ions, and a charge-transfer contribution in the fluorescence spectra of the neutral compound is absent.
• Polycyclic π-Electron System with Boron at Its Center
  作者：Shohei Saito、Kyohei Matsuo、Shigehiro Yamaguchi

  DOI：10.1021/ja3036042

  日期：2012.6.6

  We disclose a new planarized triarylborane in which the tri-coordinated boron atom is embedded in a fully fused polycyclic pi-conjugated skeleton. The compound shows high stability toward oxygen, water, and silica gel, despite the absence of steric protection around the B atom. Reflecting the electron-donating character of the pi-skeleton and the electron-accepting character of the B atom, this compound shows broad absorption bands that cover the entire visible region and a fluorescence in the visible/near-IR region. In addition, this compound shows dramatic property changes upon formation of a tetra-coordinated borate, such as thermochromic behavior in the presence of pyridine.