Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)but-2-enoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)but-2-enoate
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.27
• InChiKey: DGMQBLLKVDZUDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草醛 、 氰乙酸乙酯 在 Zr₆O₄⁽¹⁷⁵⁺⁾*6.5HO^(1-)*2C₉H₃O₆^(3-)*1.5C₈H₅NO₄^(2-)*2CHO₂^(1-)*2.5H₂O 作用下， 以 乙腈 为溶剂， 以72 %的产率得到Ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)but-2-enoate
  参考文献：
  名称：

  10.1002/cctc.202400676

  摘要：

  This work introduces a robust acid‐base catalytic system based on the zirconium‐based metal‐organic framework (Zr‐MOF) MOF‐808, selected for its open structure, high stability, and low presence of structural defects compared to other Zr‐MOFs. Four bifunctional benzoate ligands bearing free ‐COOH and N‐based groups were introduced into the MOF‐808 using solvent‐assisted ligand exchange methods. Unlike other materials, the acid and base sites in the bifunctional MOF‐808 materials are situated in the same capping ligand, leading to a bifunctional behavior between the two neighboring sites. The system was tested for Knoevenagel condensation and deacetylation‐Knoevenagel tandem reactions, demonstrating high catalytic activity and excellent yields. Additionally, computational modeling provided insights into the catalytic mechanism and the role of the acid‐base sites. The study provides a better understanding of the unique behavior of the bifunctional MOF‐808 catalyst and offers prospects for designing new and efficient catalytic systems for organocatalysis.

  DOI：

  10.1002/cctc.202400676

文献信息

• 10.1002/cctc.202400676
  作者：Moreno, José María、Gil-San-Millan, Rodrigo、Mas-Ballesté, Rubén、Alemán, José、Platero-Prats, Ana E.

  DOI：10.1002/cctc.202400676

  日期：——

  This work introduces a robust acid‐base catalytic system based on the zirconium‐based metal‐organic framework (Zr‐MOF) MOF‐808, selected for its open structure, high stability, and low presence of structural defects compared to other Zr‐MOFs. Four bifunctional benzoate ligands bearing free ‐COOH and N‐based groups were introduced into the MOF‐808 using solvent‐assisted ligand exchange methods. Unlike other materials, the acid and base sites in the bifunctional MOF‐808 materials are situated in the same capping ligand, leading to a bifunctional behavior between the two neighboring sites. The system was tested for Knoevenagel condensation and deacetylation‐Knoevenagel tandem reactions, demonstrating high catalytic activity and excellent yields. Additionally, computational modeling provided insights into the catalytic mechanism and the role of the acid‐base sites. The study provides a better understanding of the unique behavior of the bifunctional MOF‐808 catalyst and offers prospects for designing new and efficient catalytic systems for organocatalysis.