3,6-bis(imidazol-1-yl)-s-tetrazine | 929283-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,6-bis(imidazol-1-yl)-s-tetrazine
• 英文别名: 3,6-bis(1-imidazolyl)-1,2,4,5-tetrazine；3,6-bis-(1,3-imidazol-1-yl)-1,2,4,5-tetrazine；3,6-bis(imidazol-1-yl)-1,2,4,5-tetrazine；3,6-di-(imidazol-1-yl)-[1,2,4,5]tetrazine；3,6-bis(1H-imidazol-1-yl)-1,2,4,5-tetrazine；3,6-di(1H-imidazol-1-yl)-1,2,4,5-tetrazine；3,6-di(imidazol-1-yl)-1,2,4,5-tetrazine
• CAS: 929283-54-5
• 化学式: C₈H₆N₈
• 分子量: 214.189
• InChiKey: WJNVCHBURJSHLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  >360 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  571.2±33.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-bis(imidazol-1-yl)-s-tetrazine 在 mercury(II) iodide 作用下， 以 乙腈 为溶剂， 反应 5.5h， 生成 3-(1H-imidazol-1-yl)-6-methylimidazo[1,2-b][1,2,4,5]-tetrazine
  参考文献：
  名称：

  Electrophilic heterocyclization reactions of allylamino- and propargylamino-substituted sym-tetrazines in the presence of HgI2

  摘要：

  A range of 3-azolyl-6-methylimidazo[1,2-b][ 1,2,4,5] tetrazines was obtained for the first time by electrophilic heterocyclization of 6-allylamino-3-azolyl- and 3-azolyl-6-propargylamino-1,2,4,5-tetrazines in the presence of HgI2. The structures of the starting materials and final products were confirmed by H-1 and C-13 NMR spectroscopy, elemental analysis, and X-ray structural analysis.

  DOI：

  10.1007/s10593-017-2042-8
• 作为产物：
  描述：

  咪唑 、 3,6-二(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到3,6-bis(imidazol-1-yl)-s-tetrazine
  参考文献：
  名称：

  Thermally Stable 3,6-Disubstituted 1,2,4,5-Tetrazines

  摘要：

  以 3,6-双-(3,5-二甲基吡唑-1-基)-1,2,4,5-四嗪和 3,6-二氯-1,2,4,5-四嗪为亲电体，通过亲核取代反应合成了几种 3,6-二取代的 1,2,4,5-四嗪。所有新化合物都通过 1H NMR、13C NMR 和振动光谱、质谱和元素分析（C、H、N）进行了表征。为了分析热稳定性，使用了差示扫描量热法（DSC）。尤其是对称的双-3,5-二氨基-1,2,4-三唑基取代衍生物显示出极高的热稳定性，最高温度可达 370 ℃。因此，我们测定了它的能量特性，并将其与己酮二苯乙烯（HNS）的能量特性进行了比较。低温 X 射线衍射测定了 3,6-双肼基-1,2,4,5-四嗪、3,6-二氯-1,2,4,5-四嗪和 3-氨基-6-(3,5-二氨基-1,2,4-三唑-1-基)-1,2,4,5-四嗪二水合物的晶体结构。

  DOI：

  10.5560/znb.2013-3237

文献信息

• Reactions of 1,2,4,5-tetrazines with S-nucleophiles
  作者：S. G. Tolshchina、R. I. Ishmetova、N. K. Ignatenko、A. V. Korotina、I. N. Ganebnykh、V. A. Ol’shevskaya、V. N. Kalinin、G. L. Rusinov

  DOI：10.1007/s11172-011-0155-2

  日期：2011.5

  The reactions of 3,6-disubstituted and azoloannulated 1,2,4,5-tetrazines containing heterocyclic leaving groups with S-nucleophiles were studied. The methods of introduction of functionalized thiols, including thiol derivatives of 1,7- and 1,2-dicarba-closo-dodecaboranes, into the tetrazine ring were developed. It was established for the first time that, instead of replacement of a leaving group in the tetrazine ring, the attack of S-nucleophile at the unsubstituted carbon atom occurs in the case of imidazo[1,2-b][1,2,4,5]tetrazines to form previously unknown products of nucleophilic substitution of the hydrogen atom.

  研究了含有杂环离去基团的3,6-二取代和含氮唑并环的1,2,4,5-四嗪与S-亲核试剂的反应。开发了将功能化硫醇（包括1,7-和1,2-二碳硼烷硫醇衍生物）引入四嗪环的方法。首次证实，在咪唑并[1,2-b][1,2,4,5]四嗪的情况下，S-亲核试剂不是取代四嗪环中的离去基团，而是攻击未取代的碳原子，形成先前未知的氢原子亲核取代产物。
• 테트라진 기반 추진제용 아졸계 이온성 물질 및 이의 제조 방법
  申请人：AGENCY FOR DEFENSE DEVELOPMENT 국방과학연구소(319980058262) BRN ▼314-83-03869

  公开号：KR20210094851A

  公开（公告）日：2021-07-30

  본 발명은 테트라진 기반의 추진제용 아졸계 이온성 물질 및 이의 제조방법에 관한 것으로, 상세하게는 테트리진을 기반으로 1종 또는 2종의 아졸계 양이온이 서로 연결된 형태의 테트라진 기반의 아졸계 양이온을 포함하여 높은 둔감성을 가지는 것을 특징으로 하는 아졸계 이온성 물질이며, 테트라진 기반의 아졸계 양이온에서 아졸계 고리의 치환기를 나이트로화하거나, 본 발명의 테트라진 기반 추진제용 아졸계 이온성 물질의 음이온을 할로겐 이온을 포함한 다양한 음이온들로 치환을 통해 연소 속도를 조절하여 높은 폭발 열과 반응 특성을 지니는 테트라진 기반의 추진제용 아졸계 이온성 물질 및 이의 제조방법에 관한 것이다.

  本发明涉及以四氮唑为基础的推进剂用偶氮类离子性物质及其制备方法，具体包括以四氮唑为基础，包含一种或两种偶氮类阳离子相互连接的形式的四氮唑基偶氮类阳离子，具有较高的不敏感性的偶氮类离子性物质，其中通过将四氮唑基偶氮类阳离子中偶氮环的取代基硝化，或者通过用含卤离子的各种阴离子替换来调节燃烧速度，具有高爆热和反应特性的基于四氮唑的推进剂用偶氮类离子性物质及其制备方法。
• Synthesis and reactions of 7-phenylimidazo[1,2-b][1,2,4,5]tetrazines with nucleophiles
  作者：I. N. Ganebnykh、R. I. Ishmetova、S. G. Tolshchina、A. V. Korotina、D. S. Filatov、P. A. Slepukhin、G. L. Rusinov

  DOI：10.1007/s11172-018-2281-6

  日期：2018.9

  A series of novel 3-substituted 7-phenylimidazo[1,2-b][1,2,4,5]tetrazines was synthesized via the reaction of 3-R-amino-1,2,4,5-tetrazines with 2-aminoacetophenone. The structural features and possibilities of modification of 7-phenylimidazotetrazine system in the reactions with nucleophiles were studied.

  3-R-氨基-1,2,4,5-四嗪与2-R-氨基-1,2,4,5-四嗪反应合成了一系列新型3-取代7-苯基咪唑并[1,2-b][1,2,4,5]四嗪。 -氨基苯乙酮。研究了7-苯基咪唑四嗪体系在与亲核试剂反应中的结构特征和改性的可能性。
• Synthesis and antifungal activity of 3-substituted imidazo[1,2-b][1,2,4,5]tetrazines
  作者：R. I. Ishmetova、N. K. Ignatenko、I. A. Belyaninova、S. G. Tolshchina、A. V. Korotina、P. A. Slepukhin、N. P. Evstigneeva、N. V. Zil’berberg、P. G. Amineva、N. V. Kungurov、G. L. Rusinov、O. N. Chupakhin

  DOI：10.1007/s11172-015-1124-y

  日期：2015.9

  A number of new 3-substituted imidazo[1,2-b][1,2,4,5]tetrazines containing azolyl, aminopyridyl, and alkoxyl substituents was synthesized. These compounds were studied for the biological activity against mycelial anthropophilic and zoophilous dermatophyte fungi (Trichophyton, Microsporum and Epidermophyton), causing diseases of skin and its appendages (hair, nails), and yeast-like fungi Candida.

  合成了许多含有唑基、氨基吡啶基和烷氧基取代基的新型 3-取代咪唑并[1,2-b][1,2,4,5]四嗪。研究了这些化合物对导致皮肤及其附属物（头发、指甲）和酵母样真菌念珠菌的菌丝体亲人类和动物性皮肤真菌（毛癣菌、小孢子菌和表皮癣菌）的生物活性。
• In silico consensus activity prediction, rational synthesis, and evaluation of antiglycation and antiplatelet activities of 3,6-disubstituted 1,2,4,5-tetrazines
  作者：R. I. Ishmetova、D. A. Babkov、A. F. Kucheryavenko、V. A. Babkova、V. S. Sirotenko、N. K. Ignatenko、S. G. Tolschina、P. M. Vassiliev、G. L. Rusinov、A. A. Spasov

  DOI：10.1007/s11172-020-2831-6

  日期：2020.4

  consensus activity prediction, a series of 3,6-disubstituted 1,2,4,5-tetrazines were synthesized as promising inhibitors of the Maillard reaction. In addition to the studies of antiglycation activity, a comparative in vitro evaluation of the effect of the synthesized compounds on the ADP-induced rabbit platelet aggregation model was carried out. Compounds with antiglycation and antiplatelet activities significantly

  根据计算机一致活性预测，合成了一系列 3,6-二取代的 1,2,4,5-四嗪作为美拉德反应的有希望的抑制剂。除了抗糖化活性的研究外，还对合成的化合物对 ADP 诱导的兔血小板聚集模型的影响进行了体外比较评价。揭示了具有显着高于参考药物氨基胍和乙酰水杨酸的抗糖化和抗血小板活性的化合物。