2-(2-naphthyl)-3,3-dicyano-4-vinyltetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-naphthyl)-3,3-dicyano-4-vinyltetrahydrofuran
• 英文别名: 4-Ethenyl-2-naphthalen-2-yloxolane-3,3-dicarbonitrile
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: WATVCGCUMTULHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环氧丁烯 、 2-naphthylmethylidenemalononitrile 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以71%的产率得到2-(2-naphthyl)-3,3-dicyano-4-vinyltetrahydrofuran
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective [3 + 2] Cycloaddition of Vinylic Oxiranes with Activated Olefins. A Facile Synthesis of Tetrahydrofuran Derivatives

  摘要：

  The reaction of certain activated olefins (Michael accepters) 5 with vinylic oxiranes 1 in the presence of catalytic amounts of Pd(PPh3)(4) (5 mol %) in THF at 40 degrees C gave the corresponding [3 + 2] cycloaddition products 6. In all cases the reactions proceeded in regioselective manner, affording the corresponding polysubstituted tetrahydrofuran derivatives. The nature of electron-withdrawing group in activated olefins affected significantly the reactivity of substrates. Michael accepters having sterically less bulky electron-withdrawing groups were essential for the cycloaddition reaction, and the presence of two electron-withdrawing groups at the ct-position was needed. Accordingly, activated olefins having (CN, CN), (CN, CO2Et), (CN, SO2Ph), (Meldrum's type), and (SO2Ph, SO2Ph) could be used as a Michael acceptor. The present reaction provides a new method for the synthesis of tetrahydrofuran derivatives from vinylic oxiranes and Michael acceptors.

  DOI：

  10.1021/jo972317w

文献信息

• Palladium-Catalyzed Regioselective [3 + 2] Cycloaddition of Vinylic Oxiranes with Activated Olefins. A Facile Synthesis of Tetrahydrofuran Derivatives
  作者：Jae-Goo Shim、Yoshinori Yamamoto

  DOI：10.1021/jo972317w

  日期：1998.5.1

  The reaction of certain activated olefins (Michael accepters) 5 with vinylic oxiranes 1 in the presence of catalytic amounts of Pd(PPh3)(4) (5 mol %) in THF at 40 degrees C gave the corresponding [3 + 2] cycloaddition products 6. In all cases the reactions proceeded in regioselective manner, affording the corresponding polysubstituted tetrahydrofuran derivatives. The nature of electron-withdrawing group in activated olefins affected significantly the reactivity of substrates. Michael accepters having sterically less bulky electron-withdrawing groups were essential for the cycloaddition reaction, and the presence of two electron-withdrawing groups at the ct-position was needed. Accordingly, activated olefins having (CN, CN), (CN, CO2Et), (CN, SO2Ph), (Meldrum's type), and (SO2Ph, SO2Ph) could be used as a Michael acceptor. The present reaction provides a new method for the synthesis of tetrahydrofuran derivatives from vinylic oxiranes and Michael acceptors.