2-[2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl]-4H-chromen-4-one | 1184803-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-[2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl]-4H-chromen-4-one
• 英文别名: 2-[2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl]chromen-4-one
• CAS: 1184803-50-6
• 化学式: C₁₉H₁₂F₃NO₃
• 分子量: 359.304
• InChiKey: FRHMXOMMHAKCJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl]-4H-chromen-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以31%的产率得到2-(5-(2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl)-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  Synthesis of a new class of carbinol linked bis-heterocycles via the reaction of 2-(trifluoroacetyl)chromones with indoles and pyrroles

  摘要：

  2-(Trifluoroacetyl)chromones react with indoles at 90 degrees C under solvent-free conditions to produce the target (chromon-2-yl) (indol-3-yl) (trifluoromethyl)carbinols in 69-90% yields. In a similar manner, their reactions with pyrroles under the same conditions gave (chromon-2-yl) (pyrrol-2-yl) (trifluoromethyl) carbinols in 52-95% yields. These chromone derivatives react with 60% hydrazine hydrate in refluxing ethanol to give the corresponding pyrazoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.037
• 作为产物：
  描述：

  吲哚 、 2-(trifluoroacetyl)chromone 反应 5.0h， 以86%的产率得到2-[2,2,2-trifluoro-1-hydroxy-1-(1H-indol-3-yl)ethyl]-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of a new class of carbinol linked bis-heterocycles via the reaction of 2-(trifluoroacetyl)chromones with indoles and pyrroles

  摘要：

  2-(Trifluoroacetyl)chromones react with indoles at 90 degrees C under solvent-free conditions to produce the target (chromon-2-yl) (indol-3-yl) (trifluoromethyl)carbinols in 69-90% yields. In a similar manner, their reactions with pyrroles under the same conditions gave (chromon-2-yl) (pyrrol-2-yl) (trifluoromethyl) carbinols in 52-95% yields. These chromone derivatives react with 60% hydrazine hydrate in refluxing ethanol to give the corresponding pyrazoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.037

文献信息

• Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones
  作者：Roman A. Irgashev、Vyacheslav Ya. Sosnovskikh、Nataliya Kalinovich、Olesya Kazakova、Gerd-Volker Röschenthaler

  DOI：10.1016/j.tetlet.2009.06.067

  日期：2009.8

  2-(Trifluoroacetyl)chromones and 5-aryl-2-liydroxy-2-(trifluoromethyl)furan-3(2H)-ones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. (C) 2009 Elsevier Ltd. All rights reserved.