3-Phenylbicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile | 1270162-29-2

• 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-Phenylbicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile
• 英文别名: 3-phenylbicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile
• CAS: 1270162-29-2
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: OFIFMNNJOPLHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 对苯二酚 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 11.0h， 生成 3-Phenylbicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile
  参考文献：
  名称：

  Highly efficient mesoporous base catalyzed Knoevenagel condensation of different aromatic aldehydes with malononitrile and subsequent noncatalytic Diels–Alder reactions

  摘要：

  Knoevenagel condensation and [4+2] cycloaddition reactions are very important class of reactions in synthetic organic chemistry. We have prepared amino-functionalized mesoporous silica through co-condensation of 3-aminopropyltriethoxy-silane (APTES) along with tetraethylorthosilicate (TEOS) in presence of a cationic surfactant CTAB hydrothermally. Small angle powder XRD, HR TEM, FE SEM, N-2 sorption and FT IR spectroscopic tools are used to characterize the 2D-hexagonal mesostructure and to identify the presence of surface -NH2 groups in amino-functionalized mesoporous silica material. Our experimental results reveal that amino-functionalized mesoporous silica is an efficient base catalyst for the Knoevenagel condensation of different aromatic aldehydes with malononitrile to alpha,beta-unsaturated dicyanides under very mild reaction condition and in the presence of ethanol solvent. The isolated alpha,beta-unsaturated dicyanides obtained through the condensation reaction further react very efficiently with cyclopentadiene to form a series of Diels-Alder cycloaddition products in excellent yields in the absence of any catalyst. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.11.039

文献信息

• Highly efficient mesoporous base catalyzed Knoevenagel condensation of different aromatic aldehydes with malononitrile and subsequent noncatalytic Diels–Alder reactions
  作者：John Mondal、Arindam Modak、Asim Bhaumik

  DOI：10.1016/j.molcata.2010.11.039

  日期：2011.2

  Knoevenagel condensation and [4+2] cycloaddition reactions are very important class of reactions in synthetic organic chemistry. We have prepared amino-functionalized mesoporous silica through co-condensation of 3-aminopropyltriethoxy-silane (APTES) along with tetraethylorthosilicate (TEOS) in presence of a cationic surfactant CTAB hydrothermally. Small angle powder XRD, HR TEM, FE SEM, N-2 sorption and FT IR spectroscopic tools are used to characterize the 2D-hexagonal mesostructure and to identify the presence of surface -NH2 groups in amino-functionalized mesoporous silica material. Our experimental results reveal that amino-functionalized mesoporous silica is an efficient base catalyst for the Knoevenagel condensation of different aromatic aldehydes with malononitrile to alpha,beta-unsaturated dicyanides under very mild reaction condition and in the presence of ethanol solvent. The isolated alpha,beta-unsaturated dicyanides obtained through the condensation reaction further react very efficiently with cyclopentadiene to form a series of Diels-Alder cycloaddition products in excellent yields in the absence of any catalyst. (C) 2010 Elsevier B.V. All rights reserved.