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An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline: A key intermediate in the synthesis of photoaffinity probes
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2017-07-12 , DOI: 10.1016/j.tetlet.2017.07.031
Torbjörn Wixe , Fredrik Almqvist

An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline, achieving an overall yield of 38% over seven steps is reported. Only three chromatographic separations were needed and the preparation of ∼0.7 g of the target compound was demonstrated. The stability of the diazirine in solution at room temperature while exposed to ambient light was studied. No significant degradation of the compound was observed over the course of five weeks in a 130 mM sample and only minor degradation was observed in weaker samples (10, 5, and 2.5 mM), as demonstrated by 1H and 19F NMR.



中文翻译:

改进的3- [3-(三氟甲基)-3 H -1,2-二叠氮基-3-基]苯胺的合成:光亲和探针合成中的关键中间体

据报道,改进了3- [3-(三氟甲基)-3 H -1,2-二叠氮基-3-基]苯胺的合成,在七个步骤中总产率达到了38%。只需要进行三步色谱分离,就可以制备出约0.7 g的目标化合物。研究了重氮嗪在室温下暴露于环境光下在溶液中的稳定性。1 H和19 F NMR证实,在130 mM的样品中,在5周的过程中未观察到化合物的明显降解,而在较弱的样品(10、5和2.5 mM)中仅观察到了较小的降解。

更新日期:2017-07-12
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