关于合成苯丙胺类兴奋剂的赤堀-百谷反应的详细研究：第2部分。
Detailed investigations into the Akabori-Momotani reaction for the synthesis of amphetamine type stimulants: Part 2.
作者信息
Doughty David, Kent Emma, Painter Ben, Pigou Paul E, Johnston Martin R
机构信息
Flinders Centre for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, GPO Box 2100, Adelaide, South Australia 5001, Australia.
Flinders Centre for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, GPO Box 2100, Adelaide, South Australia 5001, Australia.
出版信息
Forensic Sci Int. 2018 Jun;287:207-216. doi: 10.1016/j.forsciint.2018.01.023. Epub 2018 Feb 6.
The Akabori-Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori-Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori-Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.
赤堀-百谷反应可用于由N-甲基丙氨酸和苯甲醛合成伪麻黄碱，产率为50%。本文研究了取代苯甲醛对合成苯丙胺类兴奋剂反应的电子效应，并鉴定了几种新的赤堀-百谷副产物，1-[(4-甲氧基苄基)(甲基)氨基]乙醇(11c)、2-(4-甲氧基苯基)-3,4-二甲基-1,3-恶唑烷(12c)、1,2,3,4-四甲基-5,6-二-(4-甲氧基苯基)哌嗪(13c)和1,2,4,5-四甲基-3,6-二-(4-甲氧基苯基)哌嗪(14c)。本文还借助分子模型研究了赤堀-百谷反应中伪麻黄碱和甲基苯丙胺的异构体分布，以了解为何生成的伪麻黄碱比麻黄碱更多。
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