3,6-dicyano-1,2,4,5-tetrazine | 16453-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3,6-dicyano-1,2,4,5-tetrazine
• 英文别名: 1,4-dicyanotetrazine；3.6-Dicyan-1.2.4.5-tetrazin；3,6-Dicyano-s-tetrazin；1,4-Dicyan-tetrazin；[1,2,4,5]tetrazine-3,6-dicarbonitrile；1,2,4,5-Tetrazine-3,6-dicarbonitrile
• CAS: 16453-19-3
• 化学式: C₄N₆
• 分子量: 132.084
• InChiKey: PJQACTYSHPHXNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• 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

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,6-dicyano-1,2,4,5-tetrazine 、 5-二苯并环庚烯酮 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到9-oxo-4a,9-dihydro-2H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazine-1,4-dicarbonitrile
  参考文献：
  名称：

  合成基于二苯并异戊二烯酮的新型多环π-共轭二氢哒嗪，哒嗪和吡咯

  摘要：

  研究了新型多环π共轭二氢哒嗪，哒嗪和吡咯的合成。二氢哒嗪染料是通过反电子需求的Diels-Alder环加成反应合成的，该反应是二苯并双氢肾上腺素与带有各种取代基的四嗪之间的加成反应。通过用PIFA或NO氧化添加二氢哒嗪的二苯并异丁烯酮，可以高产率合成哒嗪。哒嗪与p的电子逆反Diels-Alder反应后，还通过H位移异构化获得了哒嗪的p-醌衍生物-醌二苯并异戊二烯酮。然后通过用锌还原处理将这些哒嗪转化为相应的吡咯。观察到所有获得的二氢哒嗪在长波长下均具有吸收和发射。

  DOI：

  10.3762/bjoc.17.61
• 作为产物：
  描述：

  1,2,4,5-四嗪-3,6-二甲酰胺 在 四磷十氧化物 作用下， 160.0 ℃ 、0.13 Pa 条件下， 以10%的产率得到3,6-dicyano-1,2,4,5-tetrazine
  参考文献：
  名称：

  Structure and Properties of Nitrogen-Rich 1,4-Dicyanotetrazine, C₄N₆: A Comparative Study with Related Tetracyano Electron Acceptors

  摘要：

  The crystal structure, redox electrochemical stability, and reaction chemistry of 1,4-dicyanotetrazine (DCNT) has been experimentally characterized. These experimental results were rationalized by the results of theoretical calculations of the electronic structure, spin and charge distributions, electronic absorption spectra, and electron affinity and compared with the results for related the tetracyano electron acceptors tetracyanoethylene (TCNE), 7,7,8,8-tetracyano-p-quinodimethane (TCNQ), and 2,3,5,6-tetracyanopyrazine (TCNP). DCNT is made from the dehydration of 1,2,4,5-tetrazine-3,6-dicarboxamide, and because of the unusual deep-magenta color of the dicarboxamide in the solid state, its hydrogen-bonded layered structure, electronic structure, and electronic absorption spectra were determined. The magenta color is attributed to its absorptions at 532 nm (18 800 cm(-1)), and this corresponds to normalized chromaticity coordinates of x = 0.42 and y = 0.31 in the pink/red/orange part of the 1931 CIE chromaticity diagram. In contrast with previous reports, DCNT exhibits an irreversible one-electron reduction at -0.09 V vs SCE (MeCN) and reduced forms of DCNT have yet to be isolated and characterized. In addition, the reactions of DCNT with V(CO)(6), Fe-II(C5Me5)(2), and I- are discussed.

  DOI：

  10.1021/jo5014004

文献信息

• Electroconductive charge transfer complexes of 2,4,6-tricyano-s-triazine and of 3,6-dicyano-1,2,4,5-tetrazine with tetrathiafulvalene
  作者：Anna Berlin、Giorgio A. Pagani、Franco Sannicolò

  DOI：10.1039/c39860001579

  日期：——

  Tetrathiafulvalene afforded 1 : 1 charge transfer complexes with 3,6-dicyano-1,2,4,5-tetrazine and 2,4,6-tricyano-s-triazine: the former showed good electrical conductivity, thus proving that the attainment of aromaticity in the formed radical anion is not a necessary requisite for conductivity; the latter is a semi-conducting product which is converted by water into a new good electroconductive material

  硫富瓦烯，得到1：1个的电荷转移络合物与3,6-二氰基-1,2,4,5-四嗪和2,4,6- tricyano-小号嗪：前者表现出良好的导电性，从而证明的实现形成的自由基阴离子中的芳香性不是导电性的必要条件；后者是一种半导体产品，可通过水将其转换为新的优质导电材料。
• Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles
  作者：Ramazan Koçak、Arif Daştan

  DOI：10.3762/bjoc.17.61

  日期：——

  The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA

  研究了新型多环π共轭二氢哒嗪，哒嗪和吡咯的合成。二氢哒嗪染料是通过反电子需求的Diels-Alder环加成反应合成的，该反应是二苯并双氢肾上腺素与带有各种取代基的四嗪之间的加成反应。通过用PIFA或NO氧化添加二氢哒嗪的二苯并异丁烯酮，可以高产率合成哒嗪。哒嗪与p的电子逆反Diels-Alder反应后，还通过H位移异构化获得了哒嗪的p-醌衍生物-醌二苯并异戊二烯酮。然后通过用锌还原处理将这些哒嗪转化为相应的吡咯。观察到所有获得的二氢哒嗪在长波长下均具有吸收和发射。
• Structure and Properties of Nitrogen-Rich 1,4-Dicyanotetrazine, C₄N₆: A Comparative Study with Related Tetracyano Electron Acceptors
  作者：Hoa-Lan Vo、Jordan L. Arthur、Marçal Capdevila-Cortada、Saul H. Lapidus、Peter W. Stephens、Juan J. Novoa、Atta M. Arif、Ramneet K. Nagi、Michael H. Bartl、Joel S. Miller

  DOI：10.1021/jo5014004

  日期：2014.9.5

  The crystal structure, redox electrochemical stability, and reaction chemistry of 1,4-dicyanotetrazine (DCNT) has been experimentally characterized. These experimental results were rationalized by the results of theoretical calculations of the electronic structure, spin and charge distributions, electronic absorption spectra, and electron affinity and compared with the results for related the tetracyano electron acceptors tetracyanoethylene (TCNE), 7,7,8,8-tetracyano-p-quinodimethane (TCNQ), and 2,3,5,6-tetracyanopyrazine (TCNP). DCNT is made from the dehydration of 1,2,4,5-tetrazine-3,6-dicarboxamide, and because of the unusual deep-magenta color of the dicarboxamide in the solid state, its hydrogen-bonded layered structure, electronic structure, and electronic absorption spectra were determined. The magenta color is attributed to its absorptions at 532 nm (18 800 cm(-1)), and this corresponds to normalized chromaticity coordinates of x = 0.42 and y = 0.31 in the pink/red/orange part of the 1931 CIE chromaticity diagram. In contrast with previous reports, DCNT exhibits an irreversible one-electron reduction at -0.09 V vs SCE (MeCN) and reduced forms of DCNT have yet to be isolated and characterized. In addition, the reactions of DCNT with V(CO)(6), Fe-II(C5Me5)(2), and I- are discussed.