Lízal Tomáš, Šindelář Vladimír
Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic.
Beilstein J Org Chem. 2019 Jun 11;15:1268-1274. doi: 10.3762/bjoc.15.124. eCollection 2019.
The glycoluril monomer is a popular building block in supramolecular chemistry as it is used for the synthesis of versatile host molecules which can interact with cationic, anionic or neutral guest molecules. Here we present the design and synthesis of a new hybrid macrocycle containing glycoluril and aromatic units. The reaction afforded a mixture of macrocyclic homologues from which a two-membered macrocycle was isolated as the main product. Two disastereomers of the macrocycle were separated and characterized by means of NMR spectroscopy and X-ray crystallography. Conformational changes of these diastereomers were investigated using DFT models and variable-temperature NMR.
甘脲单体是超分子化学中一种常用的结构单元，因为它可用于合成能够与阳离子、阴离子或中性客体分子相互作用的多功能主体分子。在此，我们展示了一种含有甘脲和芳香单元的新型杂化大环化合物的设计与合成。该反应得到了大环同系物的混合物，从中分离出一种二元大环化合物作为主要产物。通过核磁共振光谱和X射线晶体学对该大环化合物的两种非对映异构体进行了分离和表征。利用密度泛函理论模型和变温核磁共振对这些非对映异构体的构象变化进行了研究。
