Synthesis, Photochemical Properties, and Cytotoxicities of 2H-Naphtho[1,2-b]pyran and Its Photodimers
Synthesis, Photochemical Properties, and Cytotoxicities of 2H-Naphtho[1,2-b]pyran and Its Photodimers
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2H-萘并[1,2-b]吡喃及其光二聚体的合成、光化学性质和细胞毒性
DOI：
10.1021/acs.joc.5b00645
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
K.
中科院分区：
文献类型：
--
作者：
Ota;M.; Sasamori;T.; Tokitoh;N.; Onodera;T.; Mizushina;Y.; Kuramochi;K.; Tsubaki;K.
2-溴-3-甲基-1，4-萘醌经二聚反应和O-甲基化反应制得的2 H-萘并[1，2-B]吡喃，经固态[2 + 2]光二聚反应，以优异的产率和选择性得到光二聚体。逆[2 + 2]环加成可以通过照射光二聚体在氯仿中的溶液来实现。有趣的是，2 H-萘并[1，2-B]吡喃在甲醇中照射或通过用六甲基二锡照射时通过骨架重排二聚化，得到2，5-二氢-1-苯并氧杂卓二聚体。此外，用三乙胺处理所得二聚体再生2 H-萘并[1，2-B]吡喃单体。观察到单体和二聚体的颜色、荧光和细胞毒性性质存在显著差异。
A 2H-naphtho[1,2-b]pyran, prepared by dimerization of 2-bromo-3-methyl-1,4-naphthoquinone andO-methylation, readily undergoes solid-state [2 + 2] photodimerization to give a photodimer in excellent yield and with excellent selectivity. Retro [2 + 2] cycloaddition can be achieved by irradiation of a solution of the photodimer in chloroform. Interestingly, the 2H-naphtho[1,2-b]pyran dimerizes with a skeletal rearrangement to afford 2,5-dihydro-1-benzoxepin dimers upon irradiation in methanol or via irradiation with hexamethylditin. Furthermore, treatment of the resulting dimers with triethylamine regenerates the 2H-naphtho[1,2-b]pyran monomer. Significant differences in the color, fluorescence, and cytotoxic properties of the monomer and dimers were observed.