5-phenyltetrazol-2-ylethene | 107933-56-2

• 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-phenyltetrazol-2-ylethene
• 英文别名: 5-phenyl-2-vinyl-2H-tetrazole；5-phenyl-2-vinyltetrazole；2-ethenyl-5-phenyltetrazole
• CAS: 107933-56-2
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: YCOIGVGFIJLESD-UHFFFAOYSA-N

物化性质

• 熔点：
  41 °C
• 沸点：
  323.9±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 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：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenyltetrazol-2-ylethene 以 邻二氯苯 为溶剂， 反应 2.0h， 以79%的产率得到3-苯基吡唑
  参考文献：
  名称：

  Moody, Christopher J.; Rees, Charles W.; Young, Richard G., Journal of the Chemical Society. Perkin transactions I, 1991, # 2, p. 329 - 333

  摘要：

  DOI：
• 作为产物：
  描述：

  trimethyl-2-(5-phenyl-2H-tetrazol-2-yl)ethylammonium bromide 在 三乙胺 作用下， 以 乙腈 为溶剂， 以100%的产率得到5-phenyltetrazol-2-ylethene
  参考文献：
  名称：

  One-pot regioselective vinylation of tetrazoles: preparation of 5-substituted 2-vinyl-2H-tetrazoles

  摘要：

  The one-pot regioselective preparation of 5-aryllalkyl-2-vinyl-2H-tetrazoles from 5-substituted tetrazoles via a very simple procedure using 1,2-clibromoethane and triethylamine without the need of any catalyst is described. The mechanism of this reaction is also discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.021

文献信息

• Vinyltetrazoles: III. Metal-catalyzed arylation, a new method of vinyltetrazoles functionalization
  作者：P. A. Aleshunin、K. A. Esikov、F. M. Dolgushin、V. A. Ostrovskii

  DOI：10.1134/s1070428012110097

  日期：2012.11

  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.
• 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., 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：——
• First examples of metal-catalyzed cross- coupling of vinyl- and ethynyltetrazoles with aryl halides
  作者：P. A. Aleshunin、K. A. Esikov、V. A. Ostrovskii

  DOI：10.1007/s10593-011-0681-8

  日期：2011.2
• MOODY, CHRISTOPHER J.;REES, CHARLES W.;YOUNG, RICHARD G., J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 329-333
  作者：MOODY, CHRISTOPHER J.、REES, CHARLES W.、YOUNG, RICHARD G.

  DOI：——

  日期：——