ethyl 4-phenyldiazenyl-3-trifluoromethyl-1H-pyrazole-5-carboxylate | 220355-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-phenyldiazenyl-3-trifluoromethyl-1H-pyrazole-5-carboxylate
• 英文别名: 3-Ethoxycarbonyl-4-phenylazo-5-trifluoromethylpyrazole；ethyl 4-phenyldiazenyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate
• CAS: 220355-48-6
• 化学式: C₁₃H₁₁F₃N₄O₂
• 分子量: 312.251
• InChiKey: TZUZEMRCYQTWQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4-phenyldiazenyl-3-trifluoromethyl-1H-pyrazole-5-carboxylate 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.83h， 以99%的产率得到4-phenyldiazenyl-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Fluorine-containing 3-arylhydrazono-2,4-dioxobutanoates in reactions with difunctional nucleophiles

  摘要：

  3-Arylhydrazono-4-polyfluoroalkyl-2,4-dioxobutanoates reacted with hydrazines to give ethyl 4-aryldiazeno-3-polyfluoroalkyl-1H-pyrazole-5-carboxylates, while analogous reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates resulted in the formation of 4-aryldiazeno-3-pentafluorophenyl-1,2-dihydropyridazine-5,6-diones or 6-aryl-7,8,9,10-tetrafluoro-2-phenyl-2,4a,6,10b-tetradropyridazo[4,3-c]cinnoline-3.4-diones, depending on the conditions. Cyclocondensation of ethyl 3-arylhydrazono-4-polyfluoroalkyl(or pentafluorophenyl)-2,4-dioxobutanoates with ethylenediamine led to 3-[1-arylhydrazono-2-oxo-2-polyfluoroalkyl(or pentafluorophenyl)ethyl]-5,6-dihydropyrazin-2(IH)-ones, and 3-[1-arylhydrazono-2-oxo-2-polyfluoroalk-yl(pentafluorophenyl)ethyl]benzoxazin-2-ones were formed in the condensation with o-aminophenol. Pentafluorophenyl-substituted heterocycles were found to undergo intramolecular ring closure to give 3-hetarylsubstituted 1-aryl-5,6,7,8-tetrafluoro-1,4-dihydrocinnolin-4-ones. The reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates with o-aminobenzenethiol gave 3-[7-(2-aminophenylsulfanyl)1-aryl-5,6,8-trifluoro-4-oxo-1,4-dihydrocinnolin-3-yl]benzothiazin-2-ones; 8a-hydroxy-11,12,13,14-tetrafluoro-10(4-methoxyphenyl)-2,3,4,5,6,7,8a, I 0-octahydropyrazino [ 1', 2': 4,5] [1,4] diazepino [6,7-c] cinnolin- 8 -one was isolated in the condensation of ethyl 3-(4-methoxyphenylhydrazono)-4-pentafluorophenyl-2,4-dioxobutanoate with N-(2-aminoethyl)ethane-1,2-diamine.

  DOI：

  10.1134/s1070428006060133
• 作为产物：
  描述：

  Ethyl 3-phenylhydrazone-5,5,5-trifluoro-2,3,4-trioxopentanoate 在 一水合肼 、 溶剂黄146 作用下， 反应 4.0h， 以67%的产率得到ethyl 4-phenyldiazenyl-3-trifluoromethyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  1,2,3-三（1,2,3,4-四）羰基化合物的氟化2（3）-芳基hydr的合成及其杂环反应

  摘要：

  1,2,3-三酮，2-芳基hydr-1,2,3-二酮酯和3-芳基--1,2,3,4-三酮酯的新的氟化2-芳基nes酮已通过氟-偶合而制备。含有1，3-酮酯，1，3-二酮，酰基（芳酰基）丙酮酸酯及其螯合物与芳基重氮氯化物。芳基azo与水合肼，苯肼，硫代氨基脲和羟胺反应生成相应的吡唑和异恶唑衍生物。3-芳基hydr-1,2,3,4-二酮酯与邻苯二胺的相互作用产生喹喔啉产物。具有五氟苯基取代基的芳基azo的分子内环化反应导致肉桂酮衍生物。

  DOI：

  10.1016/s0022-1139(98)00247-4