Coquière David, Marrot Jérôme, Reinaud Olivia
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université Paris Descartes, 45 rue des Saints-Pères, 75006 Paris, France.
Org Lett. 2007 Aug 16;9(17):3271-4. doi: 10.1021/ol071208t. Epub 2007 Jul 18.
The first synthesis of a cationic amphiphile calixarene ligand, which bears three neutral imidazole donors on one side of the hydrophobic cone and three quaternary ammonium substituents on the other side, is reported. The synthetic strategy relies on two key steps: (i) the "small rim-directed" selective ipso-nitration at the large rim and (ii) a protection-deprotection sequence of the N-alkylimidazole groups, for which two equally efficient novel methods (coordination to Zn(II) or to a cyanoborane) are presented.
据报道，首次合成了一种阳离子两亲性杯芳烃配体，该配体在疏水锥的一侧带有三个中性咪唑供体，在另一侧带有三个季铵取代基。合成策略依赖于两个关键步骤：（i）在大环边缘进行“小环导向”的选择性原位硝化；（ii）N-烷基咪唑基团的保护-脱保护序列，为此提出了两种同样有效的新方法（与Zn(II)或氰基硼烷配位）。
