由-Boc-α-氨基砜和五氟二醇合成α,α-二氟-β-氨基酮
Synthesis of α,α-Difluoro-β-amino Ketones from -Boc-α-Amidosulfones and Pentafluoro--diols.
作者信息
Islam Baharul, Sulochana Suresh P, Colby David A
机构信息
Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.
Department of Pharmaceutics and Drug Delivery, University of Mississippi, University, Mississippi 38677, United States.
出版信息
J Org Chem. 2024 May 3;89(9):6506-6512. doi: 10.1021/acs.joc.3c02181. Epub 2024 Apr 12.
Abstract
To circumvent the synthesis and isolation of imines, a method was devised to construct α,α-difluoro-β-amino ketones from -Boc-α-amidosulfones. The reactive nucleophiles, difluoroenolates, are generated in situ from the pentafluoro--diols using cesium fluoride in pyridine. NMR studies confirm the role of the α-amidosulfones in this process. Incubation of the α,α-difluoro-β-amino ketones in rat serum demonstrates the relative stability of this structure as well as its value as a chemical probe or lead.
摘要
为了避免亚胺的合成和分离，设计了一种从-Boc-α-氨基砜构建α,α-二氟-β-氨基酮的方法。反应性亲核试剂二氟烯醇盐由五氟二醇在吡啶中使用氟化铯原位生成。核磁共振研究证实了α-氨基砜在此过程中的作用。α,α-二氟-β-氨基酮在大鼠血清中的孵育证明了该结构的相对稳定性及其作为化学探针或先导物的价值。
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