trans-4-(3-(2-nitrophenyl)-3-oxoprop-1-en-1-yl)-benzonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: trans-4-(3-(2-nitrophenyl)-3-oxoprop-1-en-1-yl)-benzonitrile
• 英文别名: 4-[(E)-3-(2-nitrophenyl)-3-oxoprop-1-enyl]benzonitrile
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: SGYOFHFZGIJGGS-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-4-(3-(2-nitrophenyl)-3-oxoprop-1-en-1-yl)-benzonitrile 在 氢气 、 magnesium oxide 作用下， 以 邻二甲苯 为溶剂， 90.0 ℃ 、900.01 kPa 条件下， 反应 0.75h， 以93%的产率得到trans-4-(3-(2-aminophenyl)-3-oxoprop-1-en-1-yl)benzonitrile
  参考文献：
  名称：

  Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

  摘要：

  2'-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2'-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

  DOI：

  10.1021/cs5011713
• 作为产物：
  描述：

  邻硝基苯乙酮 、 4-氰基苯甲醛 在 magnesium oxide 作用下， 以 邻二甲苯 为溶剂， 反应 2.0h， 以83%的产率得到trans-4-(3-(2-nitrophenyl)-3-oxoprop-1-en-1-yl)-benzonitrile
  参考文献：
  名称：

  Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

  摘要：

  2'-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2'-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

  DOI：

  10.1021/cs5011713

文献信息

• US5942544A
  申请人：——

  公开号：US5942544A

  公开（公告）日：1999-08-24