4-{[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid | 644964-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-{[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid
• 英文别名: Boronic acid, [4-[[(9-anthracenylmethyl)amino]carbonyl]phenyl]-；[4-(anthracen-9-ylmethylcarbamoyl)phenyl]boronic acid
• CAS: 644964-56-7
• 化学式: C₂₂H₁₈BNO₃
• 分子量: 355.201
• InChiKey: UMUHCRBBMYYABC-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴-2-氟苯甲醚 、 4-{[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid 在 Pd(PAnPh₂)2Cl₂ [resin-CH₂N(CH₃)3]2CO₃ 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-(anthracen-9-ylmethyl)-4-(3-fluoro-4-methoxyphenyl)benzamide
  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
• 作为产物：
  描述：

  9-蒽醇 在 palladium on activated charcoal sodium azide 、 phenylhypophosphate 、 氢气 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 23.17h， 生成 4-{[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid
  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
• 作为试剂：
  描述：

  4-溴苯甲醚 、 4-氯-3-甲基苯硼酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 [resin-CH₂N(CH₃)3]2CO₃ 、 4-{[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid 、 maleimido-CH₂-PS resin 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以78%的产率得到4'-chloro-3'-methyl-1,1'-biphenyl-4-yl methyl ether
  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.