272786-89-7Relevant articles and documents
Cleavage of phosphorus-carbon (P-C) bonds of α-amino phosphonates with intramolecular hydrogen migration in the gas phase using electrospray ionization tandem mass spectrometry
Gao, Yuzhen,Xu, Jian,He, Yaohui,Tang, Guo,Lin, Zhiwei,Liu, Hongxia,Gao, Xiang,Zhao, Yufen
, p. 1964 - 1970 (2014/08/18)
RATIONALE α-Amino phosphonates with intrinsic biological activities have been used in a wide variety of applications. Because of the widespread existence of natural organophosphorus compounds containing P-C bonds such as the α-amino phosphonates, it is important to investigate the gas-phase chemistry of P-C bonds in order to determine their basic properties, which might provide some insights into their biosynthesis and catalytic cleavage. METHODS Twenty α-amino phosphonates were successfully synthesized and their fragmentation behavior was systematically investigated using in-solution deuterium labeling in combination with high-resolution Fourier transform ion cyclotron resonance (FTICR) electrospray ionization tandem mass spectrometry. RESULTS The fragmentation pathways of twenty α-amino phosphonates with different chemical structures were systematically studied. In general, P-C bonds could be easily cleaved via a novel intramolecular hydrogen atom migration from the amino group to the phosphoryl group through a five-membered-ring intermediate in the gas phase. A possible mechanism of the rearrangement of α-amino phosphonates is proposed. CONCLUSIONS An interesting intramolecular hydrogen atom migration between the amino and phosphoryl groups was observed with cleavage of the P-C bond in the molecule through a five-membered-ring intermediate. This characteristic fragmentation pathway not only provides some insights into the basic chemistry of compounds with P-C bonds, but could also have some applications in the structural determination of the α-amino phosphonate analogues. Copyright
Direct transformation of amides into α-amino phosphonates via a reductive phosphination process
Gao, Yuzhen,Huang, Zhongbin,Zhuang, Rongqiang,Xu, Jian,Zhang, Pengbo,Tang, Guo,Zhao, Yufen
supporting information, p. 4214 - 4217 (2013/09/12)
The first general method for the reductive phosphination of amides in one pot has been developed. The reactions described provide a novel access to α-amino phosphonates in good to excellent yields, cover a broad scope of substrates such as secondary and tertiary amides, and do not require a low temperature.
One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina
Ambica,Kumar, Satish,Taneja, Subhash C.,Hundal, Maninder S.,Kapoor, Kamal K.
, p. 2208 - 2212 (2008/09/18)
SbCl3 adsorbed on Al2O3 is found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl amines, aliphatic amines and esters of S-α-amino acids) and dialkylphosphites to afford the corresponding α-aminophosphonates in high yields. The ethyl ester of S-phenylalanine was observed to yield the corresponding α-aminophosphonate with S,S-diastereoisomer formed in dominance over the S,R-diastereoisomer.
