ethyl 2-(4-acetyl-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)acetate | 1352406-74-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(4-acetyl-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)acetate
• 英文别名: 4-Acetyl-1-[(ethoxycarbonyl)methyl]-5-trifluoromethyl-1,2,3-triazole；ethyl 2-[4-acetyl-5-(trifluoromethyl)triazol-1-yl]acetate
• CAS: 1352406-74-6
• 化学式: C₉H₁₀F₃N₃O₃
• 分子量: 265.192
• InChiKey: YTNGLYMINHDXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  叠氮乙酸乙酯 、 三氟乙酰丙酮 在 三乙胺 作用下， 反应 5.0h， 以48%的产率得到ethyl 2-(4-acetyl-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)acetate
  参考文献：
  名称：

  Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides

  摘要：

  1-Trifluoromethyl-substituted 1,3-dicarbonyl compounds are shown to undergo 100% regioselective cyclization in reactions with alkyl and aryl azides to form 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The reaction represents a general method for the synthesis of otherwise difficulty available 4-acyl-5trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2011.10.110

文献信息

• Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides
  作者：Yury A. Rozin、Johann Leban、Wim Dehaen、Valentine G. Nenajdenko、Vasiliy M. Muzalevskiy、Oleg S. Eltsov、Vasiliy A. Bakulev

  DOI：10.1016/j.tet.2011.10.110

  日期：2012.1

  1-Trifluoromethyl-substituted 1,3-dicarbonyl compounds are shown to undergo 100% regioselective cyclization in reactions with alkyl and aryl azides to form 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The reaction represents a general method for the synthesis of otherwise difficulty available 4-acyl-5trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. (C) 2011 Elsevier Ltd. All rights reserved,