16656-50-1

Usage

Uses

Reactant for: Synthesis of phosphonopeptidesreaction with phosphorous pentachloride

Synthesis Reference(s)

Synthesis, p. 763, 1994 DOI: 10.1055/s-1994-25564

InChI:InChI=1/C11H18NO3P.ClH/c1-3-14-16(13,15-4-2)11(12)10-8-6-5-7-9-10;/h5-9,11H,3-4,12H2,1-2H3;1H

Upstream product

• 54944-05-7 diethyl α-(2'-benzylidenehydrazino)benzylphosphonate 
• 141330-74-7 Diethyl α-<(2,3,4-Tri-O-pivaloyl-D-arabinopyranosyl)amino>benzylphosphonate 
• 762-04-9 phosphonic acid diethyl ester 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 135738-78-2 (N-Benzylidenehydrazino)benzyldiphenylphosphine oxide 
• 64244-30-0 diethyl N-benzylidene-1-amino-1-phenylmethylphosphonate 
• 100-52-7 benzaldehyde 
• 92-29-5 hydrobenzamide 
• 53378-83-9 O,O-diethyl-α-tosyloxybenzylphosphonate 
• 122-52-1 triethyl phosphite 

Downstream Products

• 81374-36-9 α-Pyrrolo-α-phenyl-methanphosphonsaeurediethylester 
• 16814-08-7 diethyl 1-aminophenylmethylphosphonate 
• 1265828-88-3 N-(1-phenylphosphonomethyl)-1-amino-1-(4-pyridyl)-methylphosphonic acid 
• 1265828-85-0 N-(1-phenylphosphonomethyl)-1-amino-1-(3-pyridyl)-methylphosphonic acid 
• 1265828-82-7 N-(1-phenyl-1-phosphonomethyl)-1-amino-1-(2-pyridyl)-methylphosphonic acid 

Relevant academic research and scientific papers

Comments on a novel synthesis of diethyl 1-aminoarylmethylphosphonates on the surface of alumina

Contrary to the literature statement we found that aromatic aldehydes react with diethyl phosphite and hexamethyldisilazane to give 1-(trimethylsilyloxy)-1-arylmethylphosphonates and not 1-amino-1-arylmethylphosphonate derivatives. Therefore, for preparat

Cyclopalladation and reactivity of amino esters through C - H bond activation: Experimental, kinetic, and density functional theory mechanistic studies

The orthopalladation, through C - H bond activation, of a large number of amino esters and amino phosphonates derived from phenylglycine, and having different substituents at the aryl ring and the C-α atom, as well as on the N-amine atom, has been studied. The experimental observations indicated an improvement in the yields of the orthopalladated compounds when the N-amine and/or the C-α atom are substituted, when compared with the unsubstituted methyl phenylglycinate derivatives. In contrast, substitutions at the aryl ring do not promote significant changes in the orthometalation results. Furthermore, the use of hydrochloride salts of the amino esters has also been shown to have a remarkably favorable effect on the process. All these observations have been fully quantified at different temperatures and pressures by a detailed kinetic study in solution in different solvents and in the presence and absence of added Bronsted acids and chloride anions. The data collected indicate relevant changes in the process depending on these conditions, as expected from the general background known for cyclopalladation reactions. An electronic mechanism of the orthopalladation has been proposed based on DFT calculations at the B3LYP level, and a very good agreement between the trends kinetically measured and the theoretically calculated activation barriers has been obtained. The reactivity of the new orthopalladated amino phosphonate derivatives has been tested and it was found that their halogenation, alkoxylation and carbonylation resulted in formation of the corresponding functionalized ortho- haloaminophosphonates, ortho-alkoxyaminophosphonates and oxoisoindolinylphosphonates. Remote control: The orthopalladation, through C - H bond activation, of substituted amino esters and amino phosphonates derived from phenylglycine has been studied (see scheme). Determination of the reaction rates indicated a clear acceleration of the C - H activation rate when the n-amine and/or the C-α atom are substituted. Substitutions at the aryl ring do not promote changes. The use of hydrochloride salts of the amino esters also has a strong accelerating effect on the process.

Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof

The invention belongs to the field of medicine chemistry and particularly relates to a cholic acid-alpha-amino phosphonate derivative and a preparation method thereof.Cholic acid and phosphate ester serve as raw materials, and the cholic acid-alpha-amino

Novel coumarin-containing aminophosphonatesas antitumor agent: synthesis, cytotoxicity, DNA-Binding and apoptosis evaluation

A series of novel coumarin-containing α-aminophosphonates were synthesized and evaluated for their antitumor activities against Human colorectal (HCT-116), human nasopharyngeal carcinoma (human KB) and human lung adenocarcinoma (MGC-803) cell lines in vit

Synthesis and solution studies of Cu(II) complexes with pyridine derivatives of iminobisphosphonic acids

New 2-pyridyl, 3-pyridyl and 4-pyridyl derivatives of iminobisphosphonic acid were prepared by addition of tris(trimethylsilyl)phosphite to the corresponding derivatives of pyridineimine-methylphosphonates 3 and subsequent methanolysis of the silylated pr

Syntheses, characterizations, and crystal structures of phosphonopeptides

α-Aminophosphonic acids and their derivatives, as phosphorus analogs of amino acids, have attracted much attention as they show a range of biological activities. In this paper, dialkyl phenyl(4-pyridylcarbonylamino)methylphosphonates were synthesized via

Sigmatropic isomerizations in azaallyl systems: XX. N- Alkylbenzimidoylphosphonates

Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives. 2004 MAIK "Nauka/Interperiodica".

Carbohydrates as chiral templates: Stereoselective synthesis of (R)- and (S)-α-aminophosphonic acid derivatives

The stereoselective synthesis of diethyl (S)- or (R)-α-[(O-pivaloyl-hexapyranosyl)amino]benzylphosphonates is achieved via Lewis acid catalyzed addition of diethyl phosphite to O-pivaloylated N-benzylidene-β-D-galactosylamine or N-benzylidene-α-D-arabinop

PHOSPHORUS ANALOGUES OF AMINO ACIDS AND PEPTIDES XII. REACTION OF SODIUM DIETHYL PHOSPHITE WITH AROMATIC ALDAZINES AND HYDRAZONES

The mechanism of the reaction of sodium diethyl phosphite with aromatic aldazines has been investigated.The initially formed monoaddition product (4) reacts with the excess of phosphorus reagent prior to the conceivable addition of diethyl phosphite to the C=N double bond.Cleavage of the N-N single bond is initiated by Single Electron Transfer from phosphite anion to the conjugated N=CH-Ph bond system.The scope of the reaction can be extended to other aromatic hydrazones.There is strong evidence to support the operation of a non-chain SET mechanism.