(E)-1,2-di(1H-tetrazol-5-yl)ethene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1,2-di(1H-tetrazol-5-yl)ethene
• 英文别名: 5-[(E)-2-(2H-tetrazol-5-yl)ethenyl]-2H-tetrazole
• 化学式: C₄H₄N₈
• 分子量: 164.129
• InChiKey: OPWDRWSFUDWILJ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反丁烯二腈 在 sodium azide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 水 、 异丙醇 为溶剂， 反应 1.0h， 以98%的产率得到(E)-1,2-di(1H-tetrazol-5-yl)ethene
  参考文献：
  名称：

  三氟甲磺酸钪在水中制备5-取代的1H-四唑

  摘要：

  摘要 采用微波加热在水或异丙醇/水混合物中制备了几种5-取代的1H-四唑。在三氟甲磺酸钪的催化下，叠氮化钠与芳基腈、脂肪腈和乙烯基腈的 [2 + 3] 环加成反应获得了良好的产率。反应通常在 160 °C 下在 3:1 的异丙醇/水混合物中加热 1 小时以获得最佳产率。图形概要

  DOI：

  10.1080/00397911.2014.957775

文献信息

• Preparation of 5-Substituted 1<i>H</i>-Tetrazoles from Nitriles in Water
  作者：Zachary P. Demko、K. Barry Sharpless

  DOI：10.1021/jo010635w

  日期：2001.11.1

  The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.

  已显示将叠氮化钠添加至腈中以生成1H-四唑在水中以锌盐为催化剂容易进行。反应范围很广。各种芳族腈，活化和未活化的烷基腈，取代的乙烯基腈，硫氰酸酯和氰胺均已证明是该反应的可行底物。
• Safe and fast tetrazole formation in ionic liquids
  作者：Boris Schmidt、Daniela Meid、Daniel Kieser

  DOI：10.1016/j.tet.2006.10.057

  日期：2007.1

  The [2+3] cycloaddition of nitriles and azides is reliable for intramolecular reactions, but the hazards with volatile azides in intermolecular reactions are tremendous. Zinc catalysis in aqueous solution is a magnificent improvement, but requires the removal of the zinc salts from the acidic product. Herein, we report safe solvents featuring low vapor pressure and good solubility of NaN3. Ionic liquids based on alkylated imidazoles combined with microwave heating turned out to be a solution for the given tasks. (c) 2006 Elsevier Ltd. All rights reserved.
• 1,3-Dipolar Cycloaddition: Click Chemistry for the Synthesis of 5-Substituted Tetrazoles from Organoaluminum Azides and Nitriles
  作者：Valentina Aureggi、Gottfried Sedelmeier

  DOI：10.1002/anie.200701045

  日期：2007.11.12
• Preparation of 5-Substituted 1<i>H</i>-Tetrazoles Catalyzed by Scandium Triflate in Water
  作者：Adiel Coca、Evan Turek、Liana Feinn

  DOI：10.1080/00397911.2014.957775

  日期：2015.1.17

  Abstract Several 5-substituted 1H-tetrazoles were prepared in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for the [2 + 3] cycloaddition of sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles when catalyzed by scandium triflate. The reactions were typically heated for 1 h at 160 °C in a 3:1 isopropanol/water mixture to obtain the best yields

  摘要 采用微波加热在水或异丙醇/水混合物中制备了几种5-取代的1H-四唑。在三氟甲磺酸钪的催化下，叠氮化钠与芳基腈、脂肪腈和乙烯基腈的 [2 + 3] 环加成反应获得了良好的产率。反应通常在 160 °C 下在 3:1 的异丙醇/水混合物中加热 1 小时以获得最佳产率。图形概要