通过4-三氟甲基-3-氧代-β-内酰胺中意外的C3-C4键断裂形成氟化酰胺酯。
Formation of Fluorinated Amido Esters through Unexpected C3-C4 Bond Fission in 4-Trifluoromethyl-3-oxo-β-lactams.
作者信息
Dao Thi Hang, Goossens Hannelore, Hertsen Dietmar, Otte Valerie, Van Nguyen Tuyen, Van Speybroeck Veronique, D'hooghe Matthias
机构信息
SynBioC Research Group, Department of Green Chemistry and Technology Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, CauGiay, Hanoi, Vietnam.
出版信息
Chem Asian J. 2018 Feb 16;13(4):421-431. doi: 10.1002/asia.201701636. Epub 2018 Jan 29.
4-Trifluoromethyl-3-oxo-β-lactams were unexpectedly transformed into 2-[(2,2-difluorovinyl)amino]-2-oxoacetates as major products, accompanied by minor amounts of 2-oxo-2-[(2,2,2-trifluoroethyl)amino]acetates, upon treatment with alkyl halides and triethylamine in DMSO. This peculiar C3-C4 bond fission reactivity was investigated in-depth, from both an experimental and a computational point of view, in order to shed light on the underlying reaction mechanism.
在二甲基亚砜中，用卤代烷和三乙胺处理时，4-三氟甲基-3-氧代-β-内酰胺意外地转化为主要产物2-[(2,2-二氟乙烯基)氨基]-2-氧代乙酸酯，并伴有少量的2-氧代-2-[(2,2,2-三氟乙基)氨基]乙酸酯。从实验和计算的角度对这种特殊的C3-C4键断裂反应活性进行了深入研究，以阐明潜在的反应机理。
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