351981-24-3Relevant academic research and scientific papers
Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells
An, Peng,Lewandowski, Tracey M.,Erbay, Tug?e G.,Liu, Peng,Lin, Qing
supporting information, p. 4860 - 4868 (2018/04/16)
In pursuit of fast bioorthogonal reactions, reactive moieties have been increasingly employed for selective labeling of biomolecules in living systems, posing a challenge in attaining reactivity without sacrificing selectivity. To address this challenge, here we report a bioinspired strategy in which molecular shape controls the selectivity of a transient, highly reactive nitrile imine dipole. By tuning the shape of structural pendants attached to the ortho position of the N-aryl ring of diaryltetrazoles-precursors of nitrile imines, we discovered a sterically shielded nitrile imine that favors the 1,3-dipolar cycloaddition over the competing nucleophilic addition. The photogenerated nitrile imine exhibits an extraordinarily long half-life of 102 s in aqueous medium, owing to its unique molecular shape that hinders the approach of a nucleophile as shown by DFT calculations. The utility of this sterically shielded nitrile imine in rapid (～1 min) bioorthogonal labeling of glucagon receptor in live mammalian cells was demonstrated.
Tandem reaction of propargyl alcohol and N-sulfonylhydrazone: Synthesis of dihydropyrazole and its utility in the preparation of 3,3-diarylacrylonitrile
Zhu, Yuanxun,Wen, Shan,Yin, Guangwei,Hong, Deng,Lu, Ping,Wang, Yanguang
supporting information; experimental part, p. 3553 - 3555 (2011/09/14)
An efficient and straightforward strategy for the synthesis of 4-methylene-1-(phenylsulfonyl)-4,5-dihydro-1H-pyrazole from propargyl alcohol and N-sulfonylhydrazone is described. N-Sulfonyl allenamide is postulated to be the key intermediate for this tandem transformation.
