methyl 5-phenyl-4-trifluoromethyl-2-pyridinecarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 5-phenyl-4-trifluoromethyl-2-pyridinecarboxylate
• 英文别名: Methyl 5-phenyl-4-(trifluoromethyl)pyridine-2-carboxylate
• 化学式: C₁₄H₁₀F₃NO₂
• 分子量: 281.234
• InChiKey: IGNGEQJHESREMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,1,1-三氟-3-苯基丙酮 在 sodium amide 作用下， 以 乙醚 、 乙酸酐 为溶剂， 反应 22.0h， 生成 methyl 5-phenyl-4-trifluoromethyl-2-pyridinecarboxylate
  参考文献：
  名称：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and Congeners as Diels−Alder Components Opening an Entry to Functionalized (Trifluoromethyl)benzenes and -pyridines

  摘要：

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifIuoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with dimethyl acetylenedicarboxylate and methyl propiolate to provide trifluoromethyl-substituted phthalates (2, 6 and 10) or benzoates (3, 7, 8 and 11). Satisfactory yields [of 4-(trifluoromethyl)pyridinecarboxylic acids 4 and 12] can even be achieved with methyl cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200205)2002:9<1490::aid-ejoc1490>3.0.co;2-1

文献信息

• 1-Ethoxy-3-trifluoromethyl-1,3-butadiene and Congeners as Diels−Alder Components Opening an Entry to Functionalized (Trifluoromethyl)benzenes and -pyridines
  作者：Jean-Noël Volle、Manfred Schlosser

  DOI：10.1002/1099-0690(200205)2002:9<1490::aid-ejoc1490>3.0.co;2-1

  日期：2002.5

  1-Ethoxy-3-trifluoromethyl-1,3-butadiene and its 2-bromo- and 2-phenyl-substituted derivatives have been prepared by Wittig methylenation of the corresponding 4-ethoxy-1,1,1-trifIuoro-3-buten-2-ones, which in turn are readily accessible from trifluoroacetic acid. The electron-rich/electron-poor dienes combine smoothly with dimethyl acetylenedicarboxylate and methyl propiolate to provide trifluoromethyl-substituted phthalates (2, 6 and 10) or benzoates (3, 7, 8 and 11). Satisfactory yields [of 4-(trifluoromethyl)pyridinecarboxylic acids 4 and 12] can even be achieved with methyl cyanoformate, a less reactive dienophile, if a large excess of the dienophile is employed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).