ethyl 2-(p-tolyl)-2H-tetrazole-5-carboxylate | 1184248-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(p-tolyl)-2H-tetrazole-5-carboxylate
• 英文别名: 2-p-tolyl-2H-tetrazole-5-carboxylic acid ethyl ester；Ethyl 2-(4-methylphenyl)tetrazole-5-carboxylate；ethyl 2-(4-methylphenyl)tetrazole-5-carboxylate
• CAS: 1184248-05-2
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: GHEUFWQTJQEUBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(p-tolyl)-2H-tetrazole-5-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以91%的产率得到2-(4-bromomethyl-phenyl)-2H-tetrazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  光反应性四唑氨基酸的合成与评价

  摘要：

  通过从头 Kakehi 四唑合成方法或通过甘氨酸席夫碱与含四唑的烷基卤化物的烷基化，有效地合成了六种光反应性四唑氨基酸，其中四种对光诱导的 1,3- 中的简单烯烃表现出优异的反应性。在乙腈/PBS 缓冲液 (1:1) 混合物中进行偶极环加成反应。

  DOI：

  10.1021/ol901300h
• 作为产物：
  描述：

  重氮乙酸乙酯 、 4-methylbenzenediazonium tetrafluoroborate 在 silver(I) acetate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 以89%的产率得到ethyl 2-(p-tolyl)-2H-tetrazole-5-carboxylate
  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

文献信息

• US2023/265077
  申请人：——

  公开号：——

  公开（公告）日：——
• Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts
  作者：Ming-Yang Xiao、Zhen Chen、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1016/j.tet.2020.131063

  日期：2020.4

  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.
• Synthesis and Evaluation of Photoreactive Tetrazole Amino Acids
  作者：Yizhong Wang、Qing Lin

  DOI：10.1021/ol901300h

  日期：2009.8.20

  Six photoreactive tetrazole amino acids were efficiently synthesized either by the de novo Kakehi tetrazole synthesis method or by alkylation of a glycine Schiff base with tetrazole-containing alkyl halides, and four of them showed excellent reactivity toward a simple alkene in the photoinduced 1,3-dipolar cycloaddition reaction in acetonitrile/PBS buffer (1:1) mixture.

  通过从头 Kakehi 四唑合成方法或通过甘氨酸席夫碱与含四唑的烷基卤化物的烷基化，有效地合成了六种光反应性四唑氨基酸，其中四种对光诱导的 1,3- 中的简单烯烃表现出优异的反应性。在乙腈/PBS 缓冲液 (1:1) 混合物中进行偶极环加成反应。