Department of Chemistry, Faculty of Science, Kanagawa University , 2946 Tsuchiya, Hiratsuka 259-1293, Japan.
Org Lett. 2015 Jan 2;17(1):138-41. doi: 10.1021/ol5031469. Epub 2014 Dec 16.
Secondary ammonium salts bearing a cyclopentyl terminal group rapidly formed pseudorotaxane with 1.5 equiv of DB24C8. Acylation of the pseudorotaxane with 50 equiv of benzoyl chloride in the presence of 50 equiv of triethylamine in toluene afforded rotaxane, the product of active transport, in 95% yield. The cyclopentyl group is small enough to allow rapid formation of pseudorotaxane, and bulky enough to facilitate the quantitative active transport by steric repulsion.
带有环戊基末端基团的仲铵盐与 1.5 当量的 DB24C8 迅速形成伪轮烷。在甲苯中，用 50 当量的三乙胺存在下，用 50 当量的苯甲酰氯酰化伪轮烷，以 95%的收率得到主动转运产物轮烷。环戊基基团足够小，可以允许快速形成伪轮烷，并且足够大，可以通过空间排斥促进定量的主动转运。
