995-14-2Relevant academic research and scientific papers
Catalyst-Free and Selective C-N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and >P(O)H Species Affording α-Aminophosphorus Compounds
Zhao, Yalei,Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
, p. 62 - 69 (2015/09/01)
Catalyst-free and selective C-N bond functionalization has been achieved through three-component coupling of amines, dihalomethane, and >P(O)H species. This reaction takes place stereospecifically with retention of configuration at phosphorus, which can produce various new optically active phosphorus analogues of α-amino acids.
Synthesis and acid-base properties of α-aminophosphoryl compounds
Zakharov,Nuriazdanova,Garifzyanov,Galkin,Cherkasov
, p. 873 - 881 (2007/10/03)
α-Aminophosphoryl compounds of the phosphonate, phosphine oxide, and α,ω-bis(phosphine oxide) series and some of their thiophosphoryl analogs were synthesized. Potentiometric measurements of the pKa of the conjugate acids revealed an insignificant effect of variation of substituents on the phosphorus, nitrogen, and α-carbon atoms on the basicity of the phosphorylated amines. The latter are weak bases. Organophosphorus groups decrease the basicity of the amines by almost 5 pK a units. The role of the hydrophobic effect and intramolecular H-bonding in the obtained substances was discussed.
NEW TYPES OF AMINOMETHYL ORGANOPHOSPHORUS COMPOUNDS
Prishchenko, A.A.,Livantsov, M.V.,Petrosyan, V.S.
, p. 1181 - 1193 (2007/10/02)
We studied aminomethylation of various PH acids their derivatives containing highly reactive PH, PSi, POSi and PC(O) fragments: tris(trimethylsilyl)phosphine, trimethylsilyl esters of phosphorus(III) acids, pivaloylphosphonite, and hydrospirophosphoranes.Chloro-, alkoxy- or dialkylaminomethylamines, dialkylformamide acetals, azomethines, and enamines were used as aminomethylating reagents.Convenient methods for synthesizing previously unknown or difficult-to-obtain organic compounds of two-, three-, four, and five-coordinate phosphorus containing a P-C-N fragment were proposed.
Reactions of aminals with amides and N-silylated amides of acids containing a three- or four-coordinate phosphorus atom
Pudovik, M.A.,Kibardina, L.K.,Terent'eva, S.A.,Pudovik, A.N.
, p. 2293 - 2297 (2007/10/02)
The reactions of 2-substituted 1,3,2-oxazaphospholidines and 1,3,2-dioxaphospholanes containing an endo- or exo-cyclic secondary amino group with aminals lead to the formation of dimers of cyclic phosphonimidates or phosphinimidates.The products of the reactions of acetylphosphoramidites and bis(trimethylsilyl)phosphoramidites with aminals and N-(alkoxymethyl)dialkylamines are dialkyl P-(aminomethyl)phosphonimidates.
REACTIONS OF N-AMINOALKYLATED 1,3,2-OXAZAPHOSPHA CYCLIC COMPOUNDS WITH PROTON-DONOR REAGENTS
Pudovik, M. A.,Terent'eva, S. A.,Pudovik, A. N.
, p. 958 - 960 (2007/10/02)
The reactions of N-aminoalkylated 1,3,2-oxazaphospha cyclic compounds with diethyl hydrogen phosphite proceed with the breakage of the aminal fragment of the bond of carbon with the endocyclic nitrogen atom and the formation of diethyl phosphonate.The aminolysis of 1,3,2-oxazaphospha cyclic compounds is accompanied by the breakage of the bond of carbon with the exocyclic nitrogen atom and leads to the formation of new N-aminoalkylate derivatives.
CHARACTERIZATION AND PROPERTIES OF SOME DIALKYL-1-(N,N-DIALKYLAMINO)ALKYLPHOSPHONATES AND THEIR HYDROCHLORIDE SALTS
Charandabi, M. R. M. D.,Ettel, M. L.,Kaushik, M. P.,Huffman, J. H.,Morse, K. W.
, p. 223 - 234 (2007/10/02)
Several new dialkyl-1-(N,N-dialkylamino)alkylphosphonates were synthesized as well as their hydrochloride salts.These compounds, along with two previously reported compounds, have been characterized by spectroscopic methods as well as elemental analysis.Spectral analysis indicates that the molecules assume an oriented posture in solution which can influence their reactivity.Additionally, the hydrochloride salts of the diethyl-1-(N,N-dimethylamino)alkylphosphonates have shown anti-viral activity.Key words: Aminoalkylphosphonate; phosphonate; NMR; HCl salt; phosphonate esters; hydrogen-bonding.
