用3-羟基-2-萘甲醇对醇类、酚类和羧酸进行光不稳定保护。
Photolabile protection of alcohols, phenols, and carboxylic acids with 3-hydroxy-2-naphthalenemethanol.
作者信息
Kulikov Anton, Arumugam Selvanathan, Popik Vladimir V
机构信息
Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
出版信息
J Org Chem. 2008 Oct 3;73(19):7611-5. doi: 10.1021/jo801302m. Epub 2008 Sep 10.
Irradiation of alcohols, phenols, and carboxylic acids "caged" with the (3-hydroxy-2-naphthalenyl)methyl group results in fast (k(release) approximately = 10(5) s(-1)) release of the substrates with good quantum (Phi = 0.17-0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (k(H2O) = 144 +/- 11 s(-1)) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide intermediate can be also trapped by other nucleophiles or converted into a photostable Diels-Alder adduct with ethyl vinyl ether.
用(3-羟基-2-萘基)甲基“笼蔽”的醇、酚和羧酸经辐照后，底物能快速释放（k(释放)约为10⁵ s⁻¹），量子产率（Φ = 0.17 - 0.26）和化学产率（>90%）良好。光反应的初始副产物2-萘醌-3-亚甲基与水快速反应（k(H₂O) = 144 ± 11 s⁻¹）生成母体3-羟基-2-萘甲醇。邻醌亚甲基中间体也可被其他亲核试剂捕获，或与乙烯基乙醚转化为光稳定的狄尔斯-阿尔德加合物。
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