Lilly Research Laboratories , Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, United States.
Org Lett. 2017 May 5;19(9):2270-2273. doi: 10.1021/acs.orglett.7b00788. Epub 2017 Apr 20.
Acyl azetidines exhibit nonplanar hybridization, leading to lower amide-like character of the corresponding (O)C-N bonds. This impacts N-acryloyl azetidines by producing enhanced electrophilicy at appended Michael acceptors. Herein, reactivity data are reported in the presence of glutathione (GSH) in phosphate buffer (pH 7.4) at 37 °C. Wide reactivity ranges are observed by varying substitution at the Michael acceptor or by modulating the electron-withdrawing character of substituents at the C3 position of the azetidine.
酰基氮杂环丁烷表现出非平面杂化，导致相应的 (O)C-N 键的酰胺样特征降低。这通过在附加的迈克尔受体上产生增强的亲电性来影响 N-丙烯酰基氮杂环丁烷。在此，在 37°C 的磷酸盐缓冲液 (pH 7.4) 中报道了谷胱甘肽 (GSH) 存在下的反应性数据。通过在迈克尔受体上改变取代基或调节氮杂环丁烷的 C3 位置取代基的吸电子特性，可以观察到广泛的反应性范围。
