1,1';3,3'-bistrimethylene-2,2'-diimidazolinylidine | 168033-07-6

• 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';3,3'-bistrimethylene-2,2'-diimidazolinylidine
• 英文别名: 1,1':3,3'-Bis(trimethylene)-2,2'-bibenzimidazolinylidene；1,8,12,19-Tetrazahexacyclo[10.10.2.02,7.08,23.013,18.019,24]tetracosa-2,4,6,13,15,17,23-heptaene
• CAS: 168033-07-6
• 化学式: C₂₀H₂₀N₄
• 分子量: 316.406
• InChiKey: JEBXVQDQKLFJHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1';3,3'-bistrimethylene-2,2'-diimidazolinylidine 在 air 作用下， 生成 1,1':3,3'-Bis(trimethylene)bis(benzimidazolone)
  参考文献：
  名称：

  桥联二苯并咪唑啉衍生物作为四氨基乙烯的新衍生物

  摘要：

  N，N′-多亚甲基桥连的双-苯并咪唑鎓盐在没有空气的情况下的去质子化反应提供了相应的桥连的二苯并咪唑啉亚基，其与双氧进行自发化学发光反应，从而得到脲烷。

  DOI：

  10.1016/0040-4039(95)00386-q
• 作为产物：
  描述：

  1,3-bis(N-benzimidazolyl)propane 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 123.0h， 生成 1,1';3,3'-bistrimethylene-2,2'-diimidazolinylidine
  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

文献信息

• An aza-analogue of TTF1: 1,1′;3,3′-bistrimethylene-2,2′-diimidazolinylidine
  作者：Zhiqiang Shi、Veronique Goulle、Randolph P. Thummel

  DOI：10.1016/0040-4039(96)00290-0

  日期：1996.4

  Bulk electrolysis of 1,1′;3,3′-bistrimethylene-2,2′-biimidazolium dibromide at −1.6 V in acetonitrile provides the air sensitive 1,1′;3,3′-bistrimethylene-2,2′-diimidazolinylidine which was characterized by 1H and 13C NMR. The corresponding dinaphtho-fused species, prepared by deprotonation of a bis-trimethylene bridged bis-naphth[2,3]imidazolium dibromide, reacts readily with air to form a syn-ureaphane

  1,1.6';; 3,3'-双三亚甲基-2,2'-二咪唑鎓二溴化物在乙腈中大量电解，对空气敏感的1,1'; 3,3'-双三亚甲基-2,2'-二咪唑啉基吡啶用1 H和13 C NMR表征。通过双三亚甲基桥联的双萘[2,3]咪唑鎓二溴化物的去质子化反应制得的相应的萘并噻吩与空气容易反应形成顺式脲基。
• 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.
• Bridged dibenzimidazolinylidenes as new derivatives of tetraaminoethylene
  作者：Zhiqiang Shi、Randolph P. Thummel

  DOI：10.1016/0040-4039(95)00386-q

  日期：1995.4

  The deprotonation of N,N′-polymethylene bridged bis-benzimidazolium salts in the absence of air provides the corresponding bridged dibenzimidazolinylidenes which undergo a spontaneous chemiluminescent reaction with dioxygen to afford ureaphanes.

  N，N′-多亚甲基桥连的双-苯并咪唑鎓盐在没有空气的情况下的去质子化反应提供了相应的桥连的二苯并咪唑啉亚基，其与双氧进行自发化学发光反应，从而得到脲烷。