N-(9-anthrylmethyl)-4-bromobenzamide | 644964-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9-anthrylmethyl)-4-bromobenzamide
• 英文别名: Benzamide, N-(9-anthracenylmethyl)-4-bromo-；N-(anthracen-9-ylmethyl)-4-bromobenzamide
• CAS: 644964-55-6
• 化学式: C₂₂H₁₆BrNO
• 分子量: 390.279
• InChiKey: GKZOGAZKNSUJFG-UHFFFAOYSA-N

物化性质

• 沸点：
  611.8±48.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  9-蒽醇 在 palladium on activated charcoal sodium azide 、 氢气 、 三溴化磷 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 N-(9-anthrylmethyl)-4-bromobenzamide
  参考文献：
  名称：

  Polymer-Assisted Solution-Phase (PASP) Suzuki Couplings Employing an Anthracene-Tagged Palladium Catalyst

  摘要：

  A general method for polymer-assisted solution-phase (PASP) Suzuki reactions employing a combination of anthracene-tagged palladium catalyst and anthracene-tagged boronic acid with a polymer-supported carbonate base is reported. The anthracene-tagged catalyst allows for the easy removal of the Pd catalyst along with the dissociated phosphine ligand and phosphine oxide byproducts by sequestration through a chemoselective Diels-Alder reaction with a maleimide resin. The polymer-supported carbonate base facilitates the removal of excess boronic acid and the borane-containing byproducts present at the end of the coupling reaction. The Suzuki coupling reaction can be efficiently conducted by using combinations of the anthracene-tagged Pd catalyst, polymer-supported carbonate base, and anthracene-tagged boronic acid to yield the desired product in high purity and yield without the use of chromatography.

  DOI：

  10.1021/jo035129g

文献信息

• Polymer-Assisted Solution-Phase (PASP) Suzuki Couplings Employing an Anthracene-Tagged Palladium Catalyst
  作者：Ping Lan、Daniela Berta、John A. Porco、Michael S. South、John J. Parlow

  DOI：10.1021/jo035129g

  日期：2003.12.1

  A general method for polymer-assisted solution-phase (PASP) Suzuki reactions employing a combination of anthracene-tagged palladium catalyst and anthracene-tagged boronic acid with a polymer-supported carbonate base is reported. The anthracene-tagged catalyst allows for the easy removal of the Pd catalyst along with the dissociated phosphine ligand and phosphine oxide byproducts by sequestration through a chemoselective Diels-Alder reaction with a maleimide resin. The polymer-supported carbonate base facilitates the removal of excess boronic acid and the borane-containing byproducts present at the end of the coupling reaction. The Suzuki coupling reaction can be efficiently conducted by using combinations of the anthracene-tagged Pd catalyst, polymer-supported carbonate base, and anthracene-tagged boronic acid to yield the desired product in high purity and yield without the use of chromatography.