Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state.
Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state.
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DOI：
10.1021/acs.orglett.5b00744
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发表时间：
2015-05-01
期刊：
影响因子：
5.2
通讯作者：
Brown RC
中科院分区：
文献类型：
--
作者：
Hill-Cousins JT;Pop IA;Pileio G;Stevanato G;Håkansson P;Roy SS;Levitt MH;Brown LJ;Brown RC
报道了一种八烷氧基取代的同位素标记的萘衍生物的合成，在单线态核磁共振实验中显示出良好的性能。这种高度取代的萘系统结合了相邻的13C自旋对，很容易从商业上可获得的13C2标记的构筑块中通过顺序的热炔基和芳基环丁烯酮重排获得。合成路线采用了一种简单的去对称化方法，导致了13C自旋对的化学位移的微小差异，这是获得核单重态顺序的关键设计约束。
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 13C spin pair, is readily accessed from a commercially available 13C2-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 13C spin pair, a design constraint crucial for accessing nuclear singlet order.