3,4'-dimethoxy-5-methyl-[1,1'-biphenyl]-2,2'-diol | 1623026-72-1

• 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: 3,4'-dimethoxy-5-methyl-[1,1'-biphenyl]-2,2'-diol
• 英文别名: 2,2'-dihydroxy-3,4'-dimethoxy-5-methylbiphenyl；2-(2-Hydroxy-4-methoxyphenyl)-6-methoxy-4-methylphenol；2-(2-hydroxy-4-methoxyphenyl)-6-methoxy-4-methylphenol
• CAS: 1623026-72-1
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: BOZAGMYBHXWYTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基苯酚 、 2-甲氧基-4-甲基苯酚 在 dipotassium peroxodisulfate 、 四丁基铵亚硫酸酯 作用下， 以 三氟乙酸 为溶剂， 反应 18.0h， 以26%的产率得到3,4'-dimethoxy-5-methyl-[1,1'-biphenyl]-2,2'-diol
  参考文献：
  名称：

  Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols

  摘要：

  An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K2S2O8 and Bu4N+.HSO3- (10 mol %) in CF3COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu4N+.HSO3-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.

  DOI：

  10.1021/acs.orglett.5b01324

文献信息

• Metal‐ and Reagent‐Free Highly Selective Anodic Cross‐Coupling Reaction of Phenols
  作者：Bernd Elsler、Dieter Schollmeyer、Katrin Marie Dyballa、Robert Franke、Siegfried R. Waldvogel

  DOI：10.1002/anie.201400627

  日期：2014.5.12

  The direct oxidative cross‐coupling of phenols is a very challenging transformation, as homo‐coupling is usually strongly preferred. Electrochemical methods circumvent the use of oxidizing reagents or metal catalysts and are therefore highly attractive. Employing electrolytes with a high capacity for hydrogen bonding, such as methanol with formic acid or 1,1,1,3,3,3‐hexafluoro‐2‐propanol, a direct

  苯酚的直接氧化交叉偶联是非常具有挑战性的转化，因为通常强烈优选均相偶联。电化学方法避免了氧化剂或金属催化剂的使用，因此极具吸引力。使用具有高氢键结合能力的电解质，例如甲醇与甲酸或1,1,1,1,3,3,3-六氟-2-丙醇，在不分隔的电池中直接电解可提供混合的2,2'-双酚具有高选择性。这种温和的方法可耐受各种部分，例如叔丁基，叔丁基与其他强亲电介质不相容，但对于随后催化成型产物的应用至关重要。
• Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.5b01324

  日期：2015.6.19

  An efficient synthesis of unsymmetrical biphenols via the oxidative cross-coupling of two different phenols in the presence of K2S2O8 and Bu4N+.HSO3- (10 mol %) in CF3COOH at ambient conditions is described. 1:1 Cross-coupling of substituted phenols with naphthols and 1:2 cross-coupling of naphthols with phenol are also disclosed. By using Bu4N+.HSO3-, the homocoupling of phenols or naphthols was controlled. In these reactions, the ortho C-H bond of two different phenols and the ortho and para C-H bond of phenols were coupled together.