2-氰基-3-(4-羟基-3-甲氧基苯基)丙酸乙酯 | 34123-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-氰基-3-(4-羟基-3-甲氧基苯基)丙酸乙酯
• 英文名称: ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)propanoate
• CAS: 34123-71-2
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: WXDYBFDJIVLXSS-UHFFFAOYSA-N

物化性质

• 沸点：
  433.5±40.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-丙烯酸,2-氰基-3-(4-羟基-3-甲氧苯基)-,乙基酯,(E)- 在 二氢吡啶 作用下， 以 乙醇 为溶剂， 以75%的产率得到2-氰基-3-(4-羟基-3-甲氧基苯基)丙酸乙酯
  参考文献：
  名称：

  Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester

  摘要：

  The Hantzsch 1,4-dihydropyridine ester (1) has been observed to be a useful selective reducing agent for the reduction of electron-withdrawing conjugated double bonds. The rate of this reaction was observed to be dependent upon the nature of the conjugated substituents and, consequently, the electronic nature of the unsaturated double bond. Theoretical calculations confirmed the importance of the HOMO-LUMO gap for this reaction and implicated a hydride transfer, agreeing with the experimentally observed reaction rate order. The calculations also revealed the importance of a boatlike structure of the 1,4-dihydropyridine nucleus as well as a trans arrangement of the ester groups to facilitate the hydride transfer.

  DOI：

  10.1021/jo034921e

文献信息

• Unprecedented Reaction between Ethyl α-Cyanocinnamate and <i>o</i>-Phenylenediamine: Development of an Efficient Method for the Transfer Hydrogenation of Electronically Depleted Olefins
  作者：Kamal Kapoor、Satish Kumar

  DOI：10.1055/s-2007-991087

  日期：——

  A reaction between ethyl α-cyanocinnamate and o-phen­ylenediamine under thermal conditions yielded 2-cyano-3-phenyl-propionic acid ethyl ester, 2-phenyl benzimidazole, and ethyl ­cyanoacetate. The mechanistic revelations led to the development of a simple and efficient transfer-hydrogenation process from the in situ generated benzimidazolines to activated olefins under solventless and catalyst-free conditions.

  在热条件下，乙基α-氰基肉桂酸酯与邻苯二胺的反应生成了2-氰基-3-苯基丙酸乙酯、2-苯基苯并咪唑和乙基氰乙酸酯。机制上的揭示促成了一种简单高效的转移氢化过程，从原位生成的苯并咪唑啉到活化烯烃，在无溶剂和无催化剂的条件下进行。