5-(azidomethyl)tetrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(azidomethyl)tetrazole
• 英文别名: 5-Azidomethyltetrazole；5-(azidomethyl)-2H-tetrazole
• 化学式: C₂H₃N₇
• 分子量: 125.093
• InChiKey: IRJSDSNUSYKSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-苯二羧酸 1,4-二-2-丙炔-1-基酯 、 5-(azidomethyl)tetrazole 以 乙醇 为溶剂， 反应 10.5h， 以41%的产率得到bis{[1-(tetrazol-5-ylmethyl)-1,2,3-triazol-4-yl]methyl} terephthalate
  参考文献：
  名称：

  Synthesis of Polycyclic Functionally-substituted Triazole- and Tetrazole-containing Systems

  摘要：

  Cycloaddition of organic mono- and diazides to the triple bond of propargyl esters of mono- and dicarboxylic acids gave rise to polycyclic 1,2,3-triazole-substituted carboxylates. Dipropargyl dicarboxylates with diazides afforded oligomeric products with alternating triazole and carboxylate fragments. Reaction of a dipropargyl ester with 5-azidomethyltetrazole furnished a tetracyclic system with alternating triazole and tetrazole rings.

  DOI：

  10.1023/b:rujo.0000045898.10072.7f
• 作为产物：
  描述：

  azidoacetonitrile 在 sodium azide 、 二乙胺盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到5-(azidomethyl)tetrazole
  参考文献：
  名称：

  Synthesis of Polynuclear Nonfused Azoles

  摘要：

  Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well as via reaction of azide ion at the cyano group of cyanomethylazoles. Initial N-(2-propynyl)azoles were prepared by reaction of 2-propynyl bromide with 1,2,3-triazoles, benzotriazole, and tetrazoles; cyanomethylazoles were obtained by alkylation of azoles with chloroacetonitrile. An analogous scheme was used to add heterocyclic units to 2-phenyl-1,2,3-triazole-4-carbonitrile. In this case, the first two heterocyclic units are linked through the ring carbon atom.

  DOI：

  10.1023/b:rujo.0000019746.10504.f3

文献信息

• Synthesis of polynuclear azoles linked through carbamate and urea bridges
  作者：T. V. Golobokova、F. A. Pokatilov、A. G. Proidakov、M. V. Kazantseva、G. G. Shevchenko、L. I. Vereshchagin、V. N. Kizhnyaev

  DOI：10.1134/s1070428012040185

  日期：2012.4

  Polynuclear azoles linked through carbamate and urea fragments were synthesized by reactions of the corresponding azolecarboxylic acid azides with heterocyclic alcohols and amines.
• Polynuclear nonfused tetrazole-, 1,3,4-oxadiazole-, and 1,2,3-triazole-containing systems
  作者：L. I. Vereshchagin、A. V. Petrov、A. G. Proidakov、F. A. Pokatilov、A. I. Smirnov、V. N. Kizhnyaev

  DOI：10.1134/s1070428006060170

  日期：2006.6

  Polynuclear nonfused blocks containing 1,2,3-triazole, 1,3,4-oxadiazole, and tetrazole rings were synthesized by reaction of C-substituted tetrazoles with carboxylic acid chlorides, as well as by cycloaddition of 2-azidomethyl-1,3,4-oxadiazoles at the triple bond of acetylenic compounds.
• Synthesis of Pentafluorosulfanylpyrazole and Pentafluorosulfanyl-1,2,3-triazole and Their Derivatives as Energetic Materials by Click Chemistry
  作者：Chengfeng Ye、Gary L. Gard、Rolf W. Winter、Robert G. Syvret、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/ol701602a

  日期：2007.9.1

  1-Pentafluorosulfanyl acetylene and its derivatives react with azide or diazomethane giving rise to an SF5-substituted 1,2,3-triazole or pyrazole. The SF5 group increases density remarkably and as a result enhances the detonation performance of the energetic materials relative to the CF3 group.
• The curtius reaction in the synthesis of noncondensed polynuclear azoles
  作者：L. I. Vereshchagin、T. V. Golobokova、F. A. Pokatilov、A. G. Proidakov、O. N. Verkhozina、A. I. Smirnov、V. N. Kizhnyaev

  DOI：10.1007/s10593-011-0781-5

  日期：2011.7

  Polynuclear noncondensed systems in which the azole rings are bound by urethane or carbamide fragments have been synthesized by the reaction of azole carboxylic acid azides with heterocyclic alcohols.