3-(4-fluorobenzoyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one | 1313223-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-fluorobenzoyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one
• 英文别名: 3-(4-Fluorobenzoyl)-4-phenyl-2-(trifluoromethyl)-2-hydroxy-2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-one；3-(4-fluorobenzoyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-4,6,7,8-tetrahydro-3H-chromen-5-one
• CAS: 1313223-82-3
• 化学式: C₂₃H₁₈F₄O₄
• 分子量: 434.387
• InChiKey: GNQCMQWTWOJMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(4-fluorobenzoyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到2-fluoro-3-(4-fluorobenzoyl)-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one
  参考文献：
  名称：

  Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones using DAST

  摘要：

  In this study, diethylaminosulfur trifluoride (DAST) was successfully applied in monofluorination reactions of some trifluoromethyl substituted 2-hydroxy-2H-chromenones, employing a general, mild, and efficient methodology. The fluorinated compounds (2-fluoro-2H-chromenones) were synthesized as unique products by a chemoselective reaction in 63-81% yield despite the presence of different reactive sites subjected to reactions with DAST. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.070
• 作为产物：
  描述：

  1-(1,1-二甲氧基乙基)-4-氟苯 在 吡啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-(4-fluorobenzoyl)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one
  参考文献：
  名称：

  The first application of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones in a three-component condensation protocol for the synthesis of 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones

  摘要：

  The one-pot, simple and efficient three-component condensation protocol for the preparation of a series of twenty-five new 3-acy1-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7.8-tetrahydro-2H-chromen-5(6H)-ones, where aryl = Ph, 4-tolyl, 4-CIPh, 4-NO2Ph and 4-CHOPh, and acyl = Ac, Bz, 4-FBz, furan-2-oyl, thien-2-oyl and naphth-1-oyl, employing 1,3-cyclohexanedione, five aryl aldehydes and for the first time, six 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluoroalk-3-en-2-ones, is described. Yields in 15-75% were obtained when the MCRs were performed in the presence of a catalytic amount of triethylamine (25 mol%) and in ethanol as solvent under reflux for 16 h. A representative X-ray diffraction data for 3-acetyl-4-phenyl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one is also showed. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.12.011

文献信息

• The first application of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones in a three-component condensation protocol for the synthesis of 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones
  作者：Helio G. Bonacorso、Jussara Navarini、Carson W. Wiethan、Guilherme P. Bortolotto、Gisele R. Paim、Susiane Cavinatto、Marcos A.P. Martins、Nilo Zanatta、Miguel S.B. Caro

  DOI：10.1016/j.jfluchem.2010.12.011

  日期：2011.3

  The one-pot, simple and efficient three-component condensation protocol for the preparation of a series of twenty-five new 3-acy1-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7.8-tetrahydro-2H-chromen-5(6H)-ones, where aryl = Ph, 4-tolyl, 4-CIPh, 4-NO2Ph and 4-CHOPh, and acyl = Ac, Bz, 4-FBz, furan-2-oyl, thien-2-oyl and naphth-1-oyl, employing 1,3-cyclohexanedione, five aryl aldehydes and for the first time, six 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluoroalk-3-en-2-ones, is described. Yields in 15-75% were obtained when the MCRs were performed in the presence of a catalytic amount of triethylamine (25 mol%) and in ethanol as solvent under reflux for 16 h. A representative X-ray diffraction data for 3-acetyl-4-phenyl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one is also showed. (C) 2010 Elsevier B.V. All rights reserved.
• Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones using DAST
  作者：Helio G. Bonacorso、Liliane M.F. Porte、Jussara Navarini、Gisele R. Paim、Fábio M. Luz、Lenon M. Oliveira、Carson W. Whietan、Marcos A.P. Martins、Nilo Zanatta

  DOI：10.1016/j.tetlet.2011.04.070

  日期：2011.6

  In this study, diethylaminosulfur trifluoride (DAST) was successfully applied in monofluorination reactions of some trifluoromethyl substituted 2-hydroxy-2H-chromenones, employing a general, mild, and efficient methodology. The fluorinated compounds (2-fluoro-2H-chromenones) were synthesized as unique products by a chemoselective reaction in 63-81% yield despite the presence of different reactive sites subjected to reactions with DAST. (C) 2011 Elsevier Ltd. All rights reserved.