环戊二烯类似物与苯醌在水中的狄尔斯-阿尔德反应及其在多环笼状化合物合成中的应用。

Shi Yijun, Liu Xuejing, Han Ying, Yan Peng, Bie Fusheng, Cao Han

Engineering and Technology Research Institute of Lunan Coal Chemical, Zaozhuang University Beian Road Zaozhuang 277160 Shandong Province China

College of Chemistry, Chemical Engineering and Materials Science, Zaozhuang University Beian Road Zaozhuang 277160 Shandong Province China.

RSC Adv. 2020 Jan 2;10(2):739-745. doi: 10.1039/c9ra09745g.

Diels-Alder reactions between cyclopentadiene analogs and -benzoquinone were explored in water and yielded 83-97% product, higher than the results reported in water with a catalyst or cetrimonium bromide (CTAB) micelles. The novel adduct 10 was synthesized and further used to synthesize the bi-cage hydrocarbon 4,4'-spirobi[pentacyclo[5.4.0.0.0.0]undecane], which has a high density (1.2663 g cm) and a high volumetric heat of combustion (53.353 MJ L). Four novel bi-cage hydrocarbon compounds were synthesized in water using this method starting from 2,2'-bi(-benzoquinone) and cyclopentadiene analogs.

研究了环戊二烯类似物与对苯醌在水中的狄尔斯-阿尔德反应，产率为83-97%，高于在水中使用催化剂或溴化十六烷基三甲基铵（CTAB）胶束所报道的结果。合成了新型加合物10，并进一步用于合成双笼状烃4,4'-螺双[五环[5.4.0.0.0.0]十一烷]，其具有高密度（1.2663 g/cm）和高体积燃烧热（53.353 MJ/L）。使用该方法，从2,2'-联（对苯醌）和环戊二烯类似物出发，在水中合成了四种新型双笼状烃化合物。