Hill-Cousins Joseph T, Pop Ionut-Alexandru, Pileio Giuseppe, Stevanato Gabriele, Håkansson Pär, Roy Soumya S, Levitt Malcolm H, Brown Lynda J, Brown Richard C D
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K.
Org Lett. 2015 May 1;17(9):2150-3. doi: 10.1021/acs.orglett.5b00744. Epub 2015 Apr 21.
The synthesis of an octa-alkoxy substituted isotopically labeled naphthalene derivative, shown to have excellent properties in singlet NMR experiments, is described. This highly substituted naphthalene system, which incorporates an adjacent (13)C spin pair, is readily accessed from a commercially available (13)C2-labeled building block via sequential thermal alkynyl- and arylcyclobutenone rearrangements. The synthetic route incorporates a simple desymmetrization approach leading to a small difference in the chemical shifts of the (13)C spin pair, a design constraint crucial for accessing nuclear singlet order.
本文描述了一种八烷氧基取代的同位素标记萘衍生物的合成，该衍生物在单重态核磁共振实验中表现出优异的性能。这种高度取代的萘体系包含相邻的(13)C自旋对，可通过连续的热炔基和芳基环丁烯酮重排，从市售的(13)C2标记的砌块轻松获得。该合成路线采用了一种简单的去对称化方法，导致(13)C自旋对的化学位移有微小差异，这是实现核单重态序的关键设计约束。
