1809-21-8Relevant articles and documents
Fluorinated phosphorus compounds: Part 11. The reactions of some fluorinated amines with dialkyl and bis(fluoroalkyl) phosphorochloridates
Timperley, Christopher M.,Waters, Matthew
, p. 1144 - 1149 (2005)
Dimethyl phosphorochloridate reacted with RFCH 2NH2 in ether in the presence of Et3N to afford (MeO)2P(O)NHCH2RF, where RF = CF3 and C2F5, in 39 and 47% yield, respectively. Similar reactions with di-n-propyl and diisopropyl phosphorochloridates could be effected only with H2NCH 2CF3 when 4-dimethylaminopyridine catalyst was added and (n-PrO)2P(O)NHCH2CF3 and (i-PrO) 2P(O)NHCH2CF3 were isolated in 49 and 25% yield, respectively. Treatment of POCl3 with one molar equivalent each of H2NCH2CF3 and Et3N permitted the synthesis of Cl2P(O)NHCH2CF3 in 43% yield. Bis(fluoroalkyl) phosphorochloridates (RFO)2P(O)Cl, where RF = C2F5CH2, C3F 7CH2 and (CF3)2CH, reacted with 2,2,2-trifluoroethylamine and 2,2,3,3,3-pentafluoropropylamine to furnish phosphoramidates (RFO)2P(O)NHCH2R, where R = CF3 or C2F5, in yields of 32-67%.
Synthesis and in vitro cytotoxicity and antibacterial activity of novel1,2,3-triazol-5-yl-phosphonates
Bálint, Erika,Hackler, László,Kari, Beáta,Puskás, László G.,Szabó, Pál Tamás,Tóth, Emese,Tripolszky, Anna
, (2020/07/02)
Novel1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.
Electrophilic trifluoromethylation of S-hydrogen phosphorothioates
Santschi, Nico,Togni, Antonio
experimental part, p. 4189 - 4193 (2011/07/31)
A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2- benziodoxole). Relative rate data were obtained by 19F NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.