3-{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-hydroxy-6-methyl-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: 3-[2-[3,5-Bis(trifluoromethyl)phenyl]prop-2-enyl]-4-hydroxy-6-methylpyran-2-one；3-[2-[3,5-bis(trifluoromethyl)phenyl]prop-2-enyl]-4-hydroxy-6-methylpyran-2-one
• 化学式: C₁₇H₁₂F₆O₃
• 分子量: 378.271
• InChiKey: VVMHEVVTSPQWOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 丙二烯 、 3,5-双(三氟甲基)碘苯 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以67%的产率得到3-{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Dihydrofurocoumarin and dihydrofurodihydropyrid-2-one derivatives via palladium catalysed cascades involving aryl/heteroaryl/vinyl iodides and allene followed by acid catalysed cyclisation

  摘要：

  Mono 3-(2'-arylallyl) derivatives of 4-hydroxycoumarin 1a,b, 4-hydroxy-6-methyl-pyran-2-one (3) and 6-hydroxy-1,4-dimethyl-1,2-dihydropyrid-2-one-3-carbonitrile (4) are produced in 3-component cascades involving aryl/heteroaryl/vinyl iodides and allene (1 atm) using Pd(PPh3)(4)/CS2CO3/MeCN/80degreesC or Pd-2(dba)(3)/tris(2-furyl)phosphine/K2CO3/DMF/80degreesC as the catalyst system. 4-Hydroxy-2-quinolone (2) afforded a mixture of mono- and bis-allylation products under these conditions. Mono C-allylation products 5a-e and 15a-e undergo facile acid catalysed cyclisation to afford dihydrofurocoumarins 11a-e and dihydrofurodihydropyrid-2-ones 16a-e in good overall yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.049

文献信息

• Dihydrofurocoumarin and dihydrofurodihydropyrid-2-one derivatives via palladium catalysed cascades involving aryl/heteroaryl/vinyl iodides and allene followed by acid catalysed cyclisation
  作者：Ronald Grigg、Mohammad Nurnabi、M.Ruhul A Sarkar

  DOI：10.1016/j.tet.2004.02.049

  日期：2004.4

  Mono 3-(2'-arylallyl) derivatives of 4-hydroxycoumarin 1a,b, 4-hydroxy-6-methyl-pyran-2-one (3) and 6-hydroxy-1,4-dimethyl-1,2-dihydropyrid-2-one-3-carbonitrile (4) are produced in 3-component cascades involving aryl/heteroaryl/vinyl iodides and allene (1 atm) using Pd(PPh3)(4)/CS2CO3/MeCN/80degreesC or Pd-2(dba)(3)/tris(2-furyl)phosphine/K2CO3/DMF/80degreesC as the catalyst system. 4-Hydroxy-2-quinolone (2) afforded a mixture of mono- and bis-allylation products under these conditions. Mono C-allylation products 5a-e and 15a-e undergo facile acid catalysed cyclisation to afford dihydrofurocoumarins 11a-e and dihydrofurodihydropyrid-2-ones 16a-e in good overall yield. (C) 2004 Elsevier Ltd. All rights reserved.