2-(4-nitro-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester | 3654-53-3

• 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-(4-nitro-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(4-nitrophenyl)-2H-tetrazole-5-carboxylate；2-(4-nitro-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester
• CAS: 3654-53-3
• 化学式: C₁₀H₉N₅O₄
• 分子量: 263.213
• InChiKey: MPXIJCALXAYYED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113.04
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(4-nitro-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester 在 吡啶-2-磺酰氟 、 二异丁基氢化铝 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 28.0h， 生成 5-(fluoromethyl)-2-(4-nitrophenyl)-2H-tetrazole
  参考文献：
  名称：

  Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

  摘要：

  Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131063
• 作为产物：
  描述：

  重氮乙酸乙酯 、 4-nitrobenzenediazonium tetrafluoroborate 在 silver(I) acetate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 以52 mg的产率得到2-(4-nitro-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

  摘要：

  Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131063