3,5-dimethylphenyl (E)-styryl ether

• 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: 3,5-dimethylphenyl (E)-styryl ether
• 英文别名: 1,3-dimethyl-5-[(E)-2-phenylethenoxy]benzene
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: GROPGYKABOOMGZ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [(Z)-2-溴乙烯基]苯 、 3,5-二甲基苯酚 在 copper(l) iodide 、 phosphazene dendrimer ligand 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以91%的产率得到3,5-dimethylphenyl (E)-styryl ether
  参考文献：
  名称：

  Enhanced Catalytic Properties of Copper in O- and N-Arylation and Vinylation Reactions, Using Phosphorus Dendrimers as Ligands

  摘要：

  Imino pyridine-capped phosphorus dendrimers were found to strongly enhance the catalytic activity of copper in arylations and vinylations of O- and N-nucleophiles. These reactions could indeed be performed under very mild conditions, often the mildest to date. Interestingly, such performances could not be obtained when using the monomeric imino pyridine chelating ligand alone. To the best of our knowledge, this constitutes a rare example of such a positive dendritic effect in the field of organometallic catalysis.

  DOI：

  10.1021/ja066505s

文献信息

• Mild Copper-Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides
  作者：Marc Taillefer、Armelle Ouali、Brice Renard、Jean-Francis Spindler

  DOI：10.1002/chem.200501411

  日期：2006.7.5

  more hindered vinyl bromides, the use of the original bidentate chelator 8 was shown to be more efficient to promote the coupling reactions than our key tetradentate ligand 3. The corresponding N-(1-alkenyl)azoles and alkenyl aryl ethers are obtained in high yields and selectivities under very mild temperature conditions (35-110 degrees C for N-vinylation reactions and 50-80 degrees C for O-vinylation

  报道了一种有效且直接的铜催化方法，该方法允许N-或O-亲核试剂被二或三取代的乙烯基溴化物乙烯基化。该程序适用于广泛的底物，因为可以用催化量的碘化铜和廉价的氮配体3或8进行单，二和三唑的N乙烯基化以及酚衍生物的O乙烯基化。对于受阻更大的乙烯基溴，与原始的四齿配体3相比，使用原始的双齿螯合剂8可以更有效地促进偶联反应。获得了相应的N-（1-烯基）唑和烯基芳基醚在非常温和的温度条件下（N-乙烯基化反应温度为35-110℃，O-乙烯基化反应温度为50-80℃）以高收率和选择性进行分离。而且，据我们所知，该方法是各种唑在铜催化的乙烯基化反应中的第一个实例。最后，与允许合成此类化合物的现有方法相比，该方案在实验室规模上可行并且易于适应工业规模，因此具有很大的竞争力。
• Enhanced Catalytic Properties of Copper in O- and N-Arylation and Vinylation Reactions, Using Phosphorus Dendrimers as Ligands
  作者：Armelle Ouali、Régis Laurent、Anne-Marie Caminade、Jean-Pierre Majoral、Marc Taillefer

  DOI：10.1021/ja066505s

  日期：2006.12.1

  Imino pyridine-capped phosphorus dendrimers were found to strongly enhance the catalytic activity of copper in arylations and vinylations of O- and N-nucleophiles. These reactions could indeed be performed under very mild conditions, often the mildest to date. Interestingly, such performances could not be obtained when using the monomeric imino pyridine chelating ligand alone. To the best of our knowledge, this constitutes a rare example of such a positive dendritic effect in the field of organometallic catalysis.