5-ethyl-1-vinyl-1H-tetrazole | 1354833-39-8

• 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-ethyl-1-vinyl-1H-tetrazole
• 英文别名: 1-ethenyl-5-ethyltetrazole
• CAS: 1354833-39-8
• 化学式: C₅H₈N₄
• 分子量: 124.145
• InChiKey: GNKXSZHGQJXNGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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 、 5-ethyl-1-vinyl-1H-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， 反应 4.0h， 以81%的产率得到1-[2-(E)-phenylethenyl]-5-ethyltetrazole
  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：

  1-乙基-1,2,3,4-四唑 、 1,2-二溴乙烷 在 三乙胺 作用下， 以 乙腈 为溶剂， 以40%的产率得到5-ethyl-2-vinyl-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