2-Methyl-3-[phenoxy(phenyl)methyl]-5-phenyl-4-prop-2-enylfuran | 1021457-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methyl-3-[phenoxy(phenyl)methyl]-5-phenyl-4-prop-2-enylfuran
• 英文别名: 2-methyl-3-[phenoxy(phenyl)methyl]-5-phenyl-4-prop-2-enylfuran
• CAS: 1021457-52-2
• 化学式: C₂₇H₂₄O₂
• 分子量: 380.486
• InChiKey: WJPARAFUBKBINR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯丙烯 、 苯酚 、 (E)-3-benzylidene-5-phenylpent-4-yn-2-one 在 双(乙腈)氯化钯(II) 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以66%的产率得到2-Methyl-3-[phenoxy(phenyl)methyl]-5-phenyl-4-prop-2-enylfuran
  参考文献：
  名称：

  2-（1-炔基）-2-烯-1-酮与亲核试剂的钯（II）催化多米诺反应：范围，机理及在3,4-氟代双环四取代呋喃合成中的合成应用

  摘要：

  Abstractmagnified imageDescribed herein is the development of a palladium(II)‐catalyzed two‐ or three‐component reaction of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with nucleophiles and allylic chlorides. Various types of nucleophiles such as O‐, N‐, C‐based nucleophiles and olefin‐tethered O‐, N‐, C‐based nucleophiles were investigated. The scope, mechanism and application of this Pd(II)‐catalyzed domino reaction were studied. In these transformations, the palladium catalyst exhibits a dual role, serving simultaneously as a Lewis acid and a transition metal. Two possible reaction pathways (cross‐coupling reaction vs. Heck reaction) from the same intermediate furanylpalladium species were observed. The reaction pathway is dependent on the property of the nucleophile and the length of the tethered chain as well. When olefin‐tethered O‐based nucleophiles were used, only the cross‐coupling reaction pathway was observed, in contrast, both reaction pathways were observed when olefin‐tethered C‐based nucleophiles were employed. The product ratio is dependent on the length of the tethered chain. Furthermore, ring‐closing metathesis (RCM) of corresponding furans with CC bonds provides an easy method for the preparation of functionalized oxygen‐heterocycles – 3,4‐fused bicyclic furans. It is also noteworthy that allylic chloride can be as an oxidant besides its well known function as an alkylating reagent.

  DOI：

  10.1002/adsc.200800715

文献信息

• Tetrasubstituted Furans by a PdII-Catalyzed Three-Component Michael Addition/Cyclization/Cross-Coupling Reaction
  作者：Yuanjing Xiao、Junliang Zhang

  DOI：10.1002/anie.200704531

  日期：2008.2.22
• Palladium(II)-Catalyzed Domino Reaction of 2-(1-Alkynyl)-2-alken-1-ones with Nucleophiles: Scope, Mechanism and Synthetic Application in the Synthesis of 3,4-Fused Bicyclic Tetrasubstituted Furans
  作者：Yuanjing Xiao、Junliang Zhang

  DOI：10.1002/adsc.200800715

  日期：2009.3

  Abstractmagnified imageDescribed herein is the development of a palladium(II)‐catalyzed two‐ or three‐component reaction of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with nucleophiles and allylic chlorides. Various types of nucleophiles such as O‐, N‐, C‐based nucleophiles and olefin‐tethered O‐, N‐, C‐based nucleophiles were investigated. The scope, mechanism and application of this Pd(II)‐catalyzed domino reaction were studied. In these transformations, the palladium catalyst exhibits a dual role, serving simultaneously as a Lewis acid and a transition metal. Two possible reaction pathways (cross‐coupling reaction vs. Heck reaction) from the same intermediate furanylpalladium species were observed. The reaction pathway is dependent on the property of the nucleophile and the length of the tethered chain as well. When olefin‐tethered O‐based nucleophiles were used, only the cross‐coupling reaction pathway was observed, in contrast, both reaction pathways were observed when olefin‐tethered C‐based nucleophiles were employed. The product ratio is dependent on the length of the tethered chain. Furthermore, ring‐closing metathesis (RCM) of corresponding furans with CC bonds provides an easy method for the preparation of functionalized oxygen‐heterocycles – 3,4‐fused bicyclic furans. It is also noteworthy that allylic chloride can be as an oxidant besides its well known function as an alkylating reagent.