3-(tricyanovinyl)-7-azaindole | 1313495-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-(tricyanovinyl)-7-azaindole
• 英文别名: 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethene-1,1,2-tricarbonitrile
• CAS: 1313495-56-5
• 化学式: C₁₂H₅N₅
• 分子量: 219.205
• InChiKey: QWGKCOIQTZFISA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(tricyanovinyl)-7-azaindole 、 copper(II) bis(trifluoromethanesulfonate) 、 N,N-二甲基甲酰胺 反应 336.0h， 以59%的产率得到[((TCVaza)4Cu2)(DMF)2]
  参考文献：
  名称：

  From discrete tricyanovinylene appended 7-azaindole copper(II) paddlewheel to an infinite 1D network: Synthesis, crystal structure and magnetic properties

  摘要：

  A tricyanovinylene appended 7-azaindole derivative (TCVazaH) was synthesized and used as a ligand for the formation of paddlewheel type complexes ([TCVaza)(4)Cu-2], 1) upon reaction with CuX2 salts. The role played by the anion X- (NO3-, TfO- or Cl) on the formation of the copper complexes was studied. Whereas for NO3- or TfO- anions, a discrete complex [(1)(DMF)(2)] was obtained, in the case of Cl-, a 1D infinite chain 2([(1)CuCl2(DMF)(4)]) was formed. The presence of the same paddlewheel core is the common feature between the discrete binuclear complex and the infinite 1D network. In both cases, the cis-(2,2) regioisomer of the binuclear unit is observed. While, in the discrete species, the axial positions of the Cu centres are occupied by DMF molecules, in the infinite chain, the DMF molecules are replaced by chloride anions leading thus to the formation of an anionic paddlewheel [(1)Cl-2](2-) unit. The bridging of the latter by [Cu(DMF)(4)](2+) cationic complexes generates the 10 chain. The study of the magnetic properties of [(1)(DMF)(2)] by magnetometry using a SQUID magnetometer revealed a strong antiferromagnetic coupling with J = -327(5) cm(-1) between the two Cu(II) centres within the paddlewheel complex. For the infinite network 2, the magnetic coupling within a paddlewheel complex is too strong for any coupling with the bridging [Cu(DMF)(4)](2+) to be observed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.06.009
• 作为产物：
  描述：

  7-氮杂吲哚 、 四氰基乙烯 在 吡啶 作用下， 以 苯 为溶剂， 反应 2.0h， 以93%的产率得到3-(tricyanovinyl)-7-azaindole
  参考文献：
  名称：

  从将乙酸铑明轮插入功能化的7-氮杂吲哚氢键二聚体到无限的结构†

  摘要：

  为了利用独特的相互作用方式，包括氢和7-氮杂吲哚核芯对四乙酸盐桨轮型配合物显示的配位键合，已经开发了一系列新的衍生物，它们在位置3处带有周边相互作用位点。制备并以固态将其自组装为二聚体H键合物种。此外，使用[Rh 2（OAc）4 ]桨轮在固态和溶液中均利用杂螯合物的结合模式，通过吡啶氮原子与Rh（II）的轴向配位产生离散的加帽配合物。）吡咯NH与赤道乙酸酯基团之一的氧原子之间的阳离子和氢键。使用带有自互补氢键供体和受体基团（例如羧基部分）的衍生物，可以实现向无限杂化网络的扩展。

  DOI：

  10.1039/c1dt10359h

文献信息

• From insertion of rhodium acetate paddlewheels into functionalized 7-azaindole hydrogen-bonded dimers to infinite architectures
  作者：Dmitry Pogozhev、Stéphane A. Baudron、Mir Wais Hosseini

  DOI：10.1039/c1dt10359h

  日期：——

  In order to take advantage of the peculiar mode of interaction consisting in the combination of hydrogen and coordination bonding displayed by the 7-azaindole core towards tetraacetate paddlewheel type complexes, a series of new derivatives, bearing peripheral interacting sites at the position 3, have been prepared and their self-assembly into dimeric H-bonded species was established in the solid state

  为了利用独特的相互作用方式，包括氢和7-氮杂吲哚核芯对四乙酸盐桨轮型配合物显示的配位键合，已经开发了一系列新的衍生物，它们在位置3处带有周边相互作用位点。制备并以固态将其自组装为二聚体H键合物种。此外，使用[Rh 2（OAc）4 ]桨轮在固态和溶液中均利用杂螯合物的结合模式，通过吡啶氮原子与Rh（II）的轴向配位产生离散的加帽配合物。）吡咯NH与赤道乙酸酯基团之一的氧原子之间的阳离子和氢键。使用带有自互补氢键供体和受体基团（例如羧基部分）的衍生物，可以实现向无限杂化网络的扩展。
• From discrete tricyanovinylene appended 7-azaindole copper(II) paddlewheel to an infinite 1D network: Synthesis, crystal structure and magnetic properties
  作者：Dmitry Pogozhev、Stéphane A. Baudron、Guillaume Rogez、Mir Wais Hosseini

  DOI：10.1016/j.poly.2012.06.009

  日期：2013.3

  A tricyanovinylene appended 7-azaindole derivative (TCVazaH) was synthesized and used as a ligand for the formation of paddlewheel type complexes ([TCVaza)(4)Cu-2], 1) upon reaction with CuX2 salts. The role played by the anion X- (NO3-, TfO- or Cl) on the formation of the copper complexes was studied. Whereas for NO3- or TfO- anions, a discrete complex [(1)(DMF)(2)] was obtained, in the case of Cl-, a 1D infinite chain 2([(1)CuCl2(DMF)(4)]) was formed. The presence of the same paddlewheel core is the common feature between the discrete binuclear complex and the infinite 1D network. In both cases, the cis-(2,2) regioisomer of the binuclear unit is observed. While, in the discrete species, the axial positions of the Cu centres are occupied by DMF molecules, in the infinite chain, the DMF molecules are replaced by chloride anions leading thus to the formation of an anionic paddlewheel [(1)Cl-2](2-) unit. The bridging of the latter by [Cu(DMF)(4)](2+) cationic complexes generates the 10 chain. The study of the magnetic properties of [(1)(DMF)(2)] by magnetometry using a SQUID magnetometer revealed a strong antiferromagnetic coupling with J = -327(5) cm(-1) between the two Cu(II) centres within the paddlewheel complex. For the infinite network 2, the magnetic coupling within a paddlewheel complex is too strong for any coupling with the bridging [Cu(DMF)(4)](2+) to be observed. (C) 2012 Elsevier Ltd. All rights reserved.