3-[Methoxy(phenyl)methyl]-2,5-diphenyl-4-prop-2-enylfuran | 1021457-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-[Methoxy(phenyl)methyl]-2,5-diphenyl-4-prop-2-enylfuran
• 英文别名: 3-[methoxy(phenyl)methyl]-2,5-diphenyl-4-prop-2-enylfuran
• CAS: 1021457-66-8
• 化学式: C₂₇H₂₄O₂
• 分子量: 380.486
• InChiKey: MXVMYRKKZWSARY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 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：

  (E)-2-benzylidene-1,4-diphenylbut-3-yn-1-one 、 甲醇 、 3-氯丙烯 在 双(乙腈)氯化钯(II) potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以91%的产率得到3-[Methoxy(phenyl)methyl]-2,5-diphenyl-4-prop-2-enylfuran
  参考文献：
  名称：

  通过Pd（II）催化的三组分Michael加成/环化/交叉偶联反应进行四取代的呋喃。

  摘要：

  DOI：

  10.1002/anie.200704531

文献信息

• 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.
• 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