水溶性主体空腔化合物中烷基α,ω-二溴化物的结合取向和反应性。
Binding orientation and reactivity of alkyl α,ω-dibromides in water-soluble cavitands.
机构信息
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. China.
出版信息
Org Biomol Chem. 2019 May 29;17(21):5279-5282. doi: 10.1039/c9ob01018a.
Host-guest complexation of long chain α,ω-dibromides was evaluated in deep water-soluble cavitands 1 and 2. The bound dibromides (C7-C12) tumble rapidly on the NMR timescale and averaged signals were observed. The complexation allows mono hydrolysis of dibromides in aqueous solution. The arrangement of the products in the host-guest complex was fixed in an unsymmetrical manner that protects the guest from further reaction. Up to 93% yields of the mono-alcohols were obtained. The α,ω-dibromides formed a capsule with cavitand 2 and remained unreactive to hydrolysis.
长链α,ω-二溴化物与主体空腔化合物 1 和 2 的主客体络合作用在深水中进行了评估。结合的二溴化物（C7-C12）在 NMR 时间尺度上迅速翻滚，观察到平均信号。该络合作用允许二溴化物在水溶液中进行单水解。在主体-客体络合物中，产物的排列以非对称的方式固定，从而保护客体免受进一步的反应。单醇的收率高达 93%。α,ω-二溴化物与空腔化合物 2 形成胶囊，且对水解保持不反应。
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