2,5-divinyl-2H-tetrazole | 97915-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-divinyl-2H-tetrazole
• 英文别名: 2-Vinyl-5-vinyltetrazole；2,5-bis(ethenyl)tetrazole
• CAS: 97915-58-7
• 化学式: C₅H₆N₄
• 分子量: 122.129
• InChiKey: XSRRAMUPXDIOPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟碘苯 、 2,5-divinyl-2H-tetrazole 在 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-vinyl-5-[2-(E)-(2-fluorophenyl)ethenyl]tetrazole
  参考文献：
  名称：

  Vinyltetrazoles: III. Metal-catalyzed arylation, a new method of vinyltetrazoles functionalization

  摘要：

  New functionalization procedure was developed for C- and N-vinyltetrazoles based on Heck reaction. Applying this method diverse (E)-styryl- and (E)-distyryltetrazoles were obtained for the first time in 76-85% yields. C-Vinyltetrazoles are more reactive in Heck cross-coupling than N-vinyltetrazoles. The arylation of 1-vinyltetrazole along Heck reaction proceeds with a C-H-activation and leads to the formation of 5-phenyl-1-[2-(E)-phenylethenyl]tetrazole.

  DOI：

  10.1134/s1070428012110097
• 作为产物：
  描述：

  5-vinyl-1,2,3,4-tetrazole 、 1,2-二溴乙烷 在 三乙胺 、 对苯二酚 作用下， 以 乙腈 为溶剂， 以60%的产率得到2,5-divinyl-2H-tetrazole
  参考文献：
  名称：

  Vinyltetrazoles: II. Synthesis of 5-substituted 1(2)-vinyltetrazoles

  摘要：

  5-R-Substituted 1(2)-vinyltetrazoles (R = Ar, Alk, CH2=CH, NH2, H) were synthesized by alkylation of 5-R-tetrazoles with 1,2-dibromoethane in the presence of triethylamine in acetonitrile, followed by elimination of triethylamine hydrobromide. Vinylation of dinuclear substrates, such as bis(1H-tetrazol-5-yl)methane and 1,3-bis(1H-tetrazol-5-yl)benzene, under analogous conditions gave the corresponding N-1, N-2'- and N-2,N-2'-divinyl derivatives.

  DOI：

  10.1134/s1070428011120177

文献信息

• Vereshchagin, L. I.; Buzilova, S. R.; Mityukova, T. K., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1777 - 1783
  作者：Vereshchagin, L. I.、Buzilova, S. R.、Mityukova, T. K.、Proidakov, A. G.、Kizhnyaev, V. N.、et al.

  DOI：——

  日期：——
• VERESHCHAGIN L. I.; BUZILOVA S. R.; MITYUKOVA T. K.; PROJDAKOV A. G.; KIZ+, ZH. ORGAN. XIMII, 22,(1986) N 9, 1979-1985
  作者：VERESHCHAGIN L. I.、 BUZILOVA S. R.、 MITYUKOVA T. K.、 PROJDAKOV A. G.、 KIZ+

  DOI：——

  日期：——