4-oxy-1-phenyl-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester | 1670-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-oxy-1-phenyl-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-oxido-1-phenyl-1,2,4-triazol-4-ium-3-carboxylate
• CAS: 1670-44-6
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: QMCYMCHXYQDKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxy-1-phenyl-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester 在 2,2,4,4-tetramethyl-3-thioxocyclobutanone 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以84%的产率得到1-Phenyl-5-thioxo-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

  摘要：

  The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and alpha-(hydroxyimino) ketones 2 in EtOH (cf: Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of Ic with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1585::aid-hlca1585>3.0.co;2-n