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Yu-Quan Hu Chen Li Bing-Xin Zhao Jun-Yong LiXiao-Jun Huang Jing LinYing Wang Wen-Cai Ye Wei-Min Chen 《Tetrahedron》2014
The photodimerization of both securinine-type and norsecurinine-type alkaloids has been investigated. The dimers of these alkaloids were obtained in a unique form of anti-head-head with high regioselectivity and stereoselectivity. Different reaction conditions were investigated and thermodynamical calculation was also carried out. It is believed that the selective dimer formation is related to the thermodynamical stability of dimeric products and the steric hindrance caused by the complex bridge rings and particular spatial structure. In addition, the norsecurinine-type alkaloids are more prone to dimerize under photochemical conditions than securinine-type alkaloids, which might result from the transannular conjugation confirmed in the securinine-type molecules. 相似文献
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