1,2,4,5-四嗪-3,6-二甲酰胺 | 36743-38-1

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,2,4,5-四嗪-3,6-二甲酰胺
• 英文名称: 1,2,4,5-tetrazine-3,6-dicarboxamide
• 英文别名: [1,2,4,5]Tetrazin-3,6-dicarbamid
• CAS: 36743-38-1
• 化学式: C₄H₄N₆O₂
• 分子量: 168.115
• InChiKey: CDGFLRLSCHJSIB-UHFFFAOYSA-N

物化性质

• 沸点：
  531.2±33.0 °C(Predicted)
• 密度：
  1.685±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硝酸 作用下， 生成 1,2,4,5-四嗪-3,6-二甲酰胺
  参考文献：
  名称：

  Silberrad, Journal of the Chemical Society, 1902, vol. 81, p. 600

  摘要：

  DOI：

文献信息

• 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。
• Diels–Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives
  作者：Nelli Rahanyan、Anthony Linden、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1039/b820551e

  日期：——

  The synthesis of a series of 3,6-disubstituted-1,2,4,5-tetrazines has been effected using an inverse electron demand [2 + 4] cycloaddition strategy. The crystal structures of 18 members of this series of diazafluoranthenes are reported. Stereochemical analysis shows that diazafluoranthenes, substituted across the bay region, are helically-twisted strained aromatic molecules. The dihedral angle between

  一系列3,6-二取代-1,2,4,5-四嗪的合成已使用反电子需量[2 + 4]环加成策略完成。据报道，该系列二氮杂蒽酮的18个成员的晶体结构。立体化学分析显示，跨海湾区域取代的二氮杂蒽酮是螺旋扭曲的应变芳族分子。哒嗪环与萘基环之间的二面角范围为0.5°至20.9°，并且遵循海湾区域的空间拥挤程度。使用M06-2X / cc-pVDZ方法将晶体结构与使用密度泛函理论确定的计算结构进行比较。
• Curtius; Darapsky; Mueller,E., Chemische Berichte, 1906, vol. 39, p. 3418
  作者：Curtius、Darapsky、Mueller,E.

  DOI：——

  日期：——
• Curtius; Darapsky; Mueller,E., Chemische Berichte, 1906, vol. 39, # 3413, p. 3417,3420,3431
  作者：Curtius、Darapsky、Mueller,E.

  DOI：——

  日期：——