1,1'-(α,α'-o-Xylyl)-2,2'-bibenzimidazole | 171072-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,1'-(α,α'-o-Xylyl)-2,2'-bibenzimidazole
• 英文别名: 6,11-dihydrobisbenzimidazo[1,2-b:2',1'-d][2,5]benzodiazocine；1,1'-(α,α'-o-xylylene)-2,2'-bibenzimidazole；o-xylbiben；3,10,19,26-Tetrazahexacyclo[17.7.0.02,10.04,9.012,17.020,25]hexacosa-1(26),2,4,6,8,12,14,16,20,22,24-undecaene
• CAS: 171072-75-6
• 化学式: C₂₂H₁₆N₄
• 分子量: 336.396
• InChiKey: BNKYWCRTVGCVRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-(α,α'-o-Xylyl)-2,2'-bibenzimidazole 在 air 、 四(二甲氨基)乙烯 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 1,1'-(α,α'-o-Xylyl)-3,3'-tetramethylenebis(benzimidazolone)
  参考文献：
  名称：

  N,N'-Bridged Derivatives of 2,2'-Bibenzimidazole

  摘要：

  A series of 2,2'-bibenzimidazolium salts has been prepared by N,N'-bridging using dihaloalkanes. These salts may be reduced by either one or two electrons to the corresponding cation radical or neutral 2,2'-bibenzimidazolylidene. The latter species undergoes a chemiluminescent reaction with dioxygen to afford conformationally unique ureaphanes. Two benzimidazole molecules may be joined by N,N'-bridges to form bis(benzimidazolium) salts which may be deprotonated with sodium hydride. Subsequent intramolecular 2,2'-coupling leads to the same 2, 8'-bibenzimidazolinylidenes. The structural features of the ureaphane oxidation products have been studied by X-ray crystallography and NMR. An equimolar mixture of a 2,2'-bibenzimidazolium salt and the corresponding 2,2'-bibenzimidazolinylidene will coproportionate to form the analogous cation radical.

  DOI：

  10.1021/jo00123a034
• 作为产物：
  描述：

  1,2-bis(benzimidazol-1-ylmethyl)benzene 在 copper diacetate 、 palladium diacetate 、 potassium carbonate 作用下， 反应 14.0h， 以42%的产率得到1,1'-(α,α'-o-Xylyl)-2,2'-bibenzimidazole
  参考文献：
  名称：

  基于C ？的多环含咪唑N-杂环的设计与合成 H活化/环化反应

  摘要：

  基于两种通用的合成方法，即通过CH / CHal和CH / CH偶联反应，Pd（II）催化的分子内芳基化反应，开发了一种合成多环咪唑N-杂环的新策略。本文提出的方法能够合成许多含有嘌呤，1-去氮杂嘌呤和苯并咪唑结构单元的稠合N-杂环。

  DOI：

  10.1002/adsc.201200221

文献信息

• Conjugated, rigidified bibenzimidazole ancillary ligands for enhanced photoluminescence quantum yields of orange/red-emitting iridium(<scp>iii</scp>) complexes
  作者：Adam F. Henwood、Daniel Antón-García、Mégane Morin、Diego Rota Martir、David B. Cordes、Colin Casey、Alexandra M. Z. Slawin、Tomas Lebl、Michael Bühl、Eli Zysman-Colman

  DOI：10.1039/c9dt00423h

  日期：——

  MesnpyH ligands confer a red-shift in the emission compared to MesppyH but maintain high photoluminescence quantum yields due to the steric bulk of the mesityl groups. The H2bibenz and o-xylbibenz ligands are shown to be electronically indistinct to dtbubpy but give complexes with higher quantum yields than analogous complexes bearing dtbubpy. In particular, the rigidity of the o-xylbibenz ligand, combined

  一系列六种新颖的[Ir（C ^ N）2（N ^ N）]（PF 6）配合物（C ^ N是两个环金属化配体之一：2-苯基-4-（2,4,6-三甲基苯基）吡啶，MesppyH，或2-（萘基-1-基）-4-（2,4,6-三甲基苯基）吡啶，MesnpyH； N ^ N表示四个中性二胺配体之一：4,4'-二叔-丁基-2,2'-二吡啶，dtbubpy，1 ħ，1' ħ -2,2'- bibenzimiazole，H 2 bibenz，1,1' - （α，α'- ö -xylylene）-2,2'-苯并咪唑，Ô合成了-xylbibenz或2,2'-biquinoline，biq），并全面表征了它们的结构，电化学和光物理性质。与MesppyH相比，更多共轭的MesnpyH配体在发射中产生红移，但由于异丁基的空间体积较大，可保持高的光致发光量子产率。H 2 bibenz和邻-xylbibenz配体显示出与dt
• Design and Synthesis of Polycyclic Imidazole‐Containing N‐ Heterocycles based on CH Activation/Cyclization Reactions
  作者：Viktor O. Iaroshenko、Dmytro Ostrovskyi、Mariia Miliutina、Aneela Maalik、Alexander Villinger、Andrei Tolmachev、Dmitriy M. Volochnyuk、Peter Langer

  DOI：10.1002/adsc.201200221

  日期：2012.9.17

  A new strategy for the synthesis of polycyclic imidazole‐containing N‐heterocycles, based on the two general synthetic ways, namely the Pd(II)‐catalyzed intramolecular arylation via CH/CHal and CH/CH coupling reactions, was developed. The method proposed here enables the synthesis of many fused N‐heterocycles containing purine, 1‐deazapurines and benzimidazole structural units.

  基于两种通用的合成方法，即通过CH / CHal和CH / CH偶联反应，Pd（II）催化的分子内芳基化反应，开发了一种合成多环咪唑N-杂环的新策略。本文提出的方法能够合成许多含有嘌呤，1-去氮杂嘌呤和苯并咪唑结构单元的稠合N-杂环。
• N,N'-Bridged Derivatives of 2,2'-Bibenzimidazole
  作者：Zhiqiang Shi、Randolph P. Thummel

  DOI：10.1021/jo00123a034

  日期：1995.9

  A series of 2,2'-bibenzimidazolium salts has been prepared by N,N'-bridging using dihaloalkanes. These salts may be reduced by either one or two electrons to the corresponding cation radical or neutral 2,2'-bibenzimidazolylidene. The latter species undergoes a chemiluminescent reaction with dioxygen to afford conformationally unique ureaphanes. Two benzimidazole molecules may be joined by N,N'-bridges to form bis(benzimidazolium) salts which may be deprotonated with sodium hydride. Subsequent intramolecular 2,2'-coupling leads to the same 2, 8'-bibenzimidazolinylidenes. The structural features of the ureaphane oxidation products have been studied by X-ray crystallography and NMR. An equimolar mixture of a 2,2'-bibenzimidazolium salt and the corresponding 2,2'-bibenzimidazolinylidene will coproportionate to form the analogous cation radical.