1-(3',4'-dimethoxy-5'-methyl-[1,1'-biphenyl]-2-yl)ethanone | 1408053-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',4'-dimethoxy-5'-methyl-[1,1'-biphenyl]-2-yl)ethanone
• CAS: 1408053-89-3
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: TWLWYRJBRDORJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-(2-溴苯基)乙醇 、 3,4-dimethoxy-2-methyliodobenzene 在 降冰片烯 、 三(2-呋喃基)膦 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以21%的产率得到1-(3',4'-dimethoxy-5'-methyl-[1,1'-biphenyl]-2-yl)ethanone
  参考文献：
  名称：

  Formation of a carbonyl group ortho to a biaryl structure or a 6H-dibenzopyran by a palladium/norbornene-catalyzed ordered reaction sequence

  摘要：

  Developments are reported in the catalytic synthesis of biaryls containing an ortho-carbaldehyde or 6H-dibenzopyrans in the presence of palladium/norbornene as catalyst. The reaction of o-substituted aryl iodides and o-bromobenzyl alcohols proceeds by unsymmetrical aryl-aryl coupling to form a seven-membered oxapalladacycle intermediate, which may undergo an intramolecular redox process to form carbonyl groups or a C-O coupling to six-membered cyclic ethers. The predominant formation of di-benzopyrans as well as of biaryl structures containing the oxidized CHO group in one ring and the reduced CH2OH in the other is described along with some mechanistic insights. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.110

文献信息

• A Sequential Pd/Norbornene-Catalyzed Process Generates <i>o-</i>Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6<i>H</i>-Dibenzopyrans by C–O Ring Closure
  作者：Elena Motti、Nicola Della Ca’、Di Xu、Anna Piersimoni、Elena Bedogni、Zhi-Ming Zhou、Marta Catellani

  DOI：10.1021/ol302889t

  日期：2012.11.16

  o-Biaryl carbaldeydes and ketones are obtained through the one-pot reaction of o-aryl iodides with o-bromobenzyl alcohols under the catalytic action of Pd and norbornene, in the presence of a base. The same reaction can also give dibenzopyrans by Pd and norbornene catalysis with a different termination, leading to C-O ring closure. In both cases the process first leads to a five-membered palladacycle, which controls C-C coupling, then to a seven-membered oxapalladacycle, which gives aldehydes and ketones or dibenzopyrans.