Biswas Atanu, Cheng Huai N, Chisholm Bret, Beni Ryan, Liu Zengshe, Vermillion Karl, Appell Michael, Forson Kelton, El Seoud Omar, Alves Carlucio R, Furtado Roselayne F
National Center for Agricultural Utilization Research, USDA Agricultural Research Services, 1815 N. University Street, Peoria, IL 61604, USA.
Southern Regional Research Center, USDA Agricultural Research Service, 1100 Allen Toussaint Boulevard, New Orleans, LA 70124, USA.
Molecules. 2025 Feb 20;30(5):977. doi: 10.3390/molecules30050977.
In this work, we report the observation of uncatalyzed ene reactions between several phenylpropanoid compounds and diethyl azodicarboxylate (DEAD). For allylbenzene, the reaction produces the ene product at molar ratios of up to 1:2 of allylbenzene to DEAD. At higher levels of DEAD, more complex reactions are observed. For the reaction between methyl eugenol and DEAD, similar ene reaction products have been found. However, the reaction of eugenol with DEAD is more complex; in addition to the ene reaction, other reactions happen at the same time. Most of the structures of the resulting products have been elucidated using NMR spectroscopy (H, C, and 2D), and the findings have been further corroborated by FTIR analysis. Interestingly, these products appear to undergo molecular aggregation, which results in self-thickening in their neat form. However, the viscosity significantly decreases upon dilution with a solvent. This self-thickening property suggests their potential use as thickening agents in organic solvent formulations.
在本研究中，我们报告了几种苯丙素类化合物与偶氮二羧酸二乙酯（DEAD）之间的无催化烯反应的观察结果。对于烯丙基苯，该反应以烯丙基苯与DEAD的摩尔比高达1:2生成烯反应产物。在DEAD含量较高时，会观察到更复杂的反应。对于丁香酚甲酯与DEAD之间的反应，也发现了类似的烯反应产物。然而，丁香酚与DEAD的反应更为复杂；除了烯反应外，同时还发生其他反应。所得产物的大多数结构已通过核磁共振光谱（H、C和二维）进行了阐明，并且这些发现已通过傅里叶变换红外光谱分析得到进一步证实。有趣的是，这些产物似乎会发生分子聚集，这导致它们在纯态时会自行增稠。然而，用溶剂稀释后粘度会显著降低。这种自增稠特性表明它们在有机溶剂配方中作为增稠剂具有潜在用途。
