p-benzoyl-o-ethynylphenol | 183589-15-3

• 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: p-benzoyl-o-ethynylphenol
• 英文别名: (3-Ethynyl-4-hydroxyphenyl)-phenylmethanone
• CAS: 183589-15-3
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: GPBBQDRSJIXQRT-UHFFFAOYSA-N

物化性质

• 熔点：
  145–146°C
• 沸点：
  402.3±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene 、 p-benzoyl-o-ethynylphenol 在 四(三苯基膦)钯 potassium acetate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 、 (3E)-5-benzoyl-3-[(4-tert-butylcyclohexen-1-yl)methylidene]-1-benzofuran-2-one 、
  参考文献：
  名称：

  钯催化邻乙炔苯酚和乙烯基三氟甲磺酸酯的环羰基化反应形成 3-Alkylidene-2-coumaranone

  摘要：

  邻乙炔苯酚与乙烯基三氟甲磺酸酯在四（三苯基膦）钯 (0) 和一氧化碳的存在下反应，以良好的收率形成 3-亚烷基-2-香豆酮。

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1137::aid-ejoc1137>3.0.co;2-8
• 作为产物：
  描述：

  1-(3-iodo-4-hydroxy-phenyl)-1-phenyl-methanone 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 p-benzoyl-o-ethynylphenol
  参考文献：
  名称：

  Palladium-Catalyzed Reaction of o-Ethynylphenols, o-((Trimethylsilyl)ethynyl)phenyl Acetates, and o-Alkynylphenols with Unsaturated Triflates or Halides:  A Route to 2-Substituted-, 2,3-Disubstituted-, and 2-Substituted-3-acylbenzo[b]furans

  摘要：

  The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)(2)(PPh(3))(2), CuI, and Et(3)N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh(3))(4), Et(3)N, and n-Bu(4)NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh(3))(4) and KOBu(t). The utilization of o-alkynylphenols 9 as the starting alkynes in the palladium-catalyzed reaction with 6 leads to the formation of 2,3-disubstituted-benzo[b]furans 13 through an annulation process promoted by sigma-vinyl- and sigma-arylpalladium complexes generated in situ. The best results in this case are obtained by using KOAc and Pd(PPh(3))(4). In the presence of KOAc and Pd(PPh(3))(4), and under an atmosphere of carbon monoxide, the reaction of o-alkynylphenols with 6 provides 2-vinyl- and 2-aryl-3-acylbenzo[b]furans 14.

  DOI：

  10.1021/jo961051a

文献信息

• Palladium-Catalyzed Reaction of <i>o</i>-Ethynylphenols, <i>o</i>-((Trimethylsilyl)ethynyl)phenyl Acetates, and <i>o</i>-Alkynylphenols with Unsaturated Triflates or Halides:  A Route to 2-Substituted-, 2,3-Disubstituted-, and 2-Substituted-3-acylbenzo[<i>b</i>]furans
  作者：Antonio Arcadi、Sandro Cacchi、Mario Del Rosario、Giancarlo Fabrizi、Fabio Marinelli

  DOI：10.1021/jo961051a

  日期：1996.1.1

  The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)(2)(PPh(3))(2), CuI, and Et(3)N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh(3))(4), Et(3)N, and n-Bu(4)NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh(3))(4) and KOBu(t). The utilization of o-alkynylphenols 9 as the starting alkynes in the palladium-catalyzed reaction with 6 leads to the formation of 2,3-disubstituted-benzo[b]furans 13 through an annulation process promoted by sigma-vinyl- and sigma-arylpalladium complexes generated in situ. The best results in this case are obtained by using KOAc and Pd(PPh(3))(4). In the presence of KOAc and Pd(PPh(3))(4), and under an atmosphere of carbon monoxide, the reaction of o-alkynylphenols with 6 provides 2-vinyl- and 2-aryl-3-acylbenzo[b]furans 14.
• Palladium-Catalyzed Cyclocarbonylation ofo-Ethynylphenols and Vinyl Triflates To Form 3-Alkylidene-2-coumaranones
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Leonardo Moro

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1137::aid-ejoc1137>3.0.co;2-8

  日期：1999.5

  o-Ethynylphenols react with vinyl triflates, in the presence of tetrakis(triphenylphosphane)palladium(0) and under carbon monoxide, to form 3-alkylidene-2-coumaranones in good yield.

  邻乙炔苯酚与乙烯基三氟甲磺酸酯在四（三苯基膦）钯 (0) 和一氧化碳的存在下反应，以良好的收率形成 3-亚烷基-2-香豆酮。