文献类型：期刊文献

英文题名：On the formation of a side product with hexahydroaporphine-like structure in the Grewe cyclization of dextromethorphan

作者：Zhao, Qiao[1,2];Zhao, Kai[1,2];Wu, Sheng-ying[1,2,3,4,5];Tian, Bo-xue[3];Eriksson, Leif A.[4,5];Wang, Li-min[1,2];An, Na[5];Long, Zhong-zhu[5];Cai, Shui-hong[5]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ Calif San Francisco, Sch Pharm, Dept Pharmaceut Chem, San Francisco, CA 94158 USA;[4]Univ Gothenburg, Dept Chem & Mol Biol, S-40530 Gothenburg, Sweden;[5]Dongyue Pharma Ltd Co, Shanghai, Peoples R China

年份：2017

卷号：43

期号：3

起止页码：1689

外文期刊名：RESEARCH ON CHEMICAL INTERMEDIATES

收录：;EI(收录号：20163902837760);WOS:【SCI-EXPANDED(收录号:WOS:000394374600027)】；

基金：The work was supported by the National Nature Science Foundation of China (NSFC, 21272069, 20672035), the Fundamental Research Funds for the Central Universities, the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, the Swedish research council, and the Faculty of science at University of Gothenburg.

语种：英文

外文关键词：Grewe cyclization; Dextromethorphan; Hexahydroaporphine-like side product; DFT calculation

摘要：Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.