1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile | 55786-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile
• 英文别名: 2,3-dicyanopyrazino[2,3-f][4,7]phenanthroline；2,3-Dicyanpyrido<2,3-f:3',2'-h>chinoxalin；dipyrido[2,3-f;3',2'-h]quinoxaline-2,3-dicarbonitrile；2,3-Dicyanodipyrido(2,3-f:3',2'-h)quinoxaline；pyrazino[2,3-f][4,7]phenanthroline-2,3-dicarbonitrile
• CAS: 55786-06-6
• 化学式: C₁₆H₆N₆
• 分子量: 282.264
• InChiKey: ORJFLARTQGRVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile 在 硫酸 作用下， 反应 72.0h， 以79%的产率得到1,4,5,12-tetraazatriphenylene-2,3-dicarboxylic acid diamide
  参考文献：
  名称：

  Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives

  摘要：

  Condensation of 5,6-diamino-4,7-phenanthroline with glyoxal provides 1,4,5,12-tetraazatriphenylene in quantitative yield. This procedure avoids the 50% loss of product inherent in previous methods. Derivatives were also prepared by using alpha-dicarbonyl compounds other than glyoxal. Additional derivatives were prepared from 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile, produced by condensation of diaminomaleonitrile with 4,7-phenanthroline-5,6-dione.

  DOI：

  10.1021/jo0495283
• 作为产物：
  描述：

  泛喹酮 、 二氨基马来腈 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile
  参考文献：
  名称：

  Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives

  摘要：

  Condensation of 5,6-diamino-4,7-phenanthroline with glyoxal provides 1,4,5,12-tetraazatriphenylene in quantitative yield. This procedure avoids the 50% loss of product inherent in previous methods. Derivatives were also prepared by using alpha-dicarbonyl compounds other than glyoxal. Additional derivatives were prepared from 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile, produced by condensation of diaminomaleonitrile with 4,7-phenanthroline-5,6-dione.

  DOI：

  10.1021/jo0495283

文献信息

• Studies on the solvatochromic effect and NLO response in new symmetric bimetallic Rhenium compounds
  作者：Iván González、Diego Cortés-Arriagada、Paulina Dreyse、Luis Sanhueza、Irma Crivelli、Hoang Minh Ngo、Isabelle Ledoux-Rak、Alejandro Toro-Labbe、Jerónimo Maze、Bárbara Loeb

  DOI：10.1016/j.poly.2020.114679

  日期：2020.9

  (Re(CO)3Cl)2μ-N^N, with NΛN 2,3-Dicarboxypyrazino[2,3-f] [4] , [7] phenanthrolinedicarboxylic (L1), or 2,3-Diethoxycarbonylypyrazino[2,3-f] [4] , [7] phenanthroline (L2). Specifically, the physicochemical, solvatochromic, and nonlinear optical behaviour of the complexes were measured. DFT calculations were also performed, in order to improve the understanding of the observed phenomena. Spectroscopic characterization

  摘要在寻找具有增强的非线性光学活性的新型配位配合物时，报道了掺有聚吡啶平面桥联配体的对称双金属R配合物。研究的络合物是（Re（CO）3Cl）2μ-N^ N类型，具有NΛN2,3-二羧基吡嗪并[2,3-f] [4]，[7]菲咯啉二羧酸（L1）或2,3 -二乙氧基羰基吡嗪并[2，3-f] [4]，[7]菲咯啉（L2）。具体而言，测量了配合物的物理化学，溶剂变色和非线性光学行为。为了提高对观察到的现象的理解，还进行了DFT计算。光谱表征显示与电荷转移相关的低能吸收带，该电荷转移涉及从from中心和氯化物配体向桥接配体的电子跃迁（Re（d）+ Cl（n）→L1（π*）; Re（d）两种络合物均为+ Cl（n）→L2（π*））。这些谱带在很大程度上取决于溶剂的极性。此行为表明电子密度的重新分布，主要是在与L1形成的复合物中观察到的。如所预期的，观察到了溶剂致变色效应与所分析的复合物的NLO响应之间的
• Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives
  作者：Chandima Abeywickrama、Arthur David Baker

  DOI：10.1021/jo0495283

  日期：2004.10.1

  Condensation of 5,6-diamino-4,7-phenanthroline with glyoxal provides 1,4,5,12-tetraazatriphenylene in quantitative yield. This procedure avoids the 50% loss of product inherent in previous methods. Derivatives were also prepared by using alpha-dicarbonyl compounds other than glyoxal. Additional derivatives were prepared from 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile, produced by condensation of diaminomaleonitrile with 4,7-phenanthroline-5,6-dione.