1-乙烯基-5-甲基四唑 | 97915-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-乙烯基-5-甲基四唑
• 英文名称: 5-methyl-1-vinyl-1H-tetrazole
• 英文别名: 5-methyl-1-vinyl-5H-tetrazole；1-Vinyl-5-methyltetrazole；5-methyl-1-vinyltetrazole；N-vinyl-5-methyltetrazole；1-Ethenyl-5-methyl-1H-tetrazole；1-ethenyl-5-methyltetrazole
• CAS: 97915-55-4
• 化学式: C₄H₆N₄
• 分子量: 110.118
• InChiKey: HZVMRQVMVRBDNS-UHFFFAOYSA-N

物化性质

• 沸点：
  214.3±23.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  碘苯 、 1-乙烯基-5-甲基四唑 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， 反应 4.0h， 以80%的产率得到5-methyl-1-[2-(E)-phenylethenyl]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-甲基四氮唑 、 乙酸乙烯酯 在 三氟化硼乙醚 、 mercury(II) diacetate 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 5-methyl-2-vinyl-2H-tetrazole 、 1-乙烯基-5-甲基四唑
  参考文献：
  名称：

  Vereshchagin, L. I.; Buzilova, S. R.; Mityukova, T. K., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1777 - 1783

  摘要：

  DOI：

文献信息

• Vinyltetrazoles: II. Synthesis of 5-substituted 1(2)-vinyltetrazoles
  作者：P. A. Aleshunin、U. N. Dmitrieva、V. A. Ostrovskii

  DOI：10.1134/s1070428011120177

  日期：2011.12

  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.
• 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：——
• 1H, 13C and 15N NMR study of vinyltetrazolium salts and processes of their synthesis
  作者：P.N Gaponik、O.A Ivashkevish、V.N Naumenko、T.B Kovalyova、T.N Andreeva、A.O Koren

  DOI：10.1016/0584-8539(93)80268-f

  日期：1993.1

  The H-1, C-13 and N-15 NMR spectra of several N- and C-vinyltetrazolium salts have been recorded and the observed chemical shifts together with the data of quantum-chemical calculations have been used for evaluation of electronic structure of the investigated substances and selectivity of the exhaustive alkylation of 1,5- and 2,5-substituted tetrazoles.