1,2-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxamide | 872266-81-4

• 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
• 英文名称: 1,2-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxamide
• 英文别名: 1,2-Dihydro-[1,2,4,5]tetrazin-3,6-dicarbamid；1,4-Dihydro-1,2,4,5-tetrazine-3,6-dicarboxamide
• CAS: 872266-81-4
• 化学式: C₄H₆N₆O₂
• 分子量: 170.131
• InChiKey: LQYMFAMGBUCRTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >280 °C
• 沸点：
  369.8±25.0 °C(Predicted)
• 密度：
  2.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 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：
  135
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxamide 在 一氧化二氮 作用下， 以 水 为溶剂， 以82%的产率得到1,2,4,5-四嗪-3,6-二甲酰胺
  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：

  dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate 在 氨 作用下， 以 乙醇 为溶剂， 以97%的产率得到1,2-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxamide
  参考文献：
  名称：

  1,4-二氢-1,2,4,5-四嗪-3,6-二羧酸酯和酰胺的合成

  摘要：

  合成了1,4-二氢-1,2,4,5-四嗪-3,6-二羧酸的烷基酯和烷基酰胺，并通过IR、1H NMR、EI-MS和元素分析对其进行了表征。1,4-二氢-1,2,4,5-四嗪-3,6-二羧酸的结构由X射线衍射分析证实。一些选定的化合物针对 P-388 和 A-549 癌细胞系进行了评估，但显示出较差的抑制活性。

  DOI：

  10.3184/030823409x12532880130972

文献信息

• 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。
• Silberrad, Journal of the Chemical Society, 1902, vol. 81, p. 600
  作者：Silberrad

  DOI：——

  日期：——
• Curtius; Lang, Journal fur praktische Chemie (Leipzig 1954), 1888, vol. <2> 38, p. 544
  作者：Curtius、Lang

  DOI：——

  日期：——
• Curtius; Lang, Journal fur praktische Chemie (Leipzig 1954), 1888, vol. <2> 38, p. 531
  作者：Curtius、Lang

  DOI：——

  日期：——
• Curtius; Darapsky; Mueller,E., Chemische Berichte, 1906, vol. 39, # 3414, p. 3429,3430
  作者：Curtius、Darapsky、Mueller,E.

  DOI：——

  日期：——