18855-52-2

Usage

Uses

Used in Organic Synthesis:
TETRAETHYL DIMETHYLAMINOMETHYLENEDIPHOSPHONATE is used as a reagent for the Horner-Wadsworth-Emmons olefination reaction with aldehydes. This reaction produces the phosphonato enamine, which can be readily converted to the homologous acid. This process is valuable in the synthesis of various organic compounds and pharmaceuticals, as it allows for the formation of new carbon-carbon bonds and the introduction of functional groups.

InChI:InChI=1/C11H27NO6P2/c1-7-15-19(13,16-8-2)11(12(5)6)20(14,17-9-3)18-10-4/h11H,7-10H2,1-6H3/p+1

Upstream product

• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 762-04-9 phosphonic acid diethyl ester 
• 29712-30-9 (dimethylaminomethylene)diphosphonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 25419-97-0 diethyl <(dimethylamino)methoxymethyl>phosphonate 
• 23587-65-7 Dimethylphosphono-ethylmercapto-dimethylamino-methan 
• 3724-43-4 Vilsmeier reagent 
• 25420-05-7 diethyl dimethyliminomethylphosphonate chloride 
• 56043-45-9 N,N,N',N'-tetramethylchlorformamidinium chloride 
• 122-52-1 triethyl phosphite 
• 13716-45-5 diethyl trimethylsilyl phosphite 
• 119949-72-3 diethyl phosphonate 
• 68-12-2 N,N-dimethyl-formamide 
• 617-84-5 N-formyldiethylamine 

Downstream Products

• 29712-30-9 (dimethylaminomethylene)diphosphonic acid 
• 18855-48-6 ((1E,3E)-1-Dimethylamino-4-phenyl-buta-1,3-dienyl)-phosphonic acid diethyl ester 
• 87627-17-6 4-oxo-3-phenyl-4H-1-benzopyran-8-acetic acid 
• 82670-82-4 ((Z)-1-Dimethylamino-3-phenyl-propenyl)-phosphonic acid diethyl ester 
• 79054-43-6 [(E)-1-Dimethylamino-2-(4-nitro-phenyl)-vinyl]-phosphonic acid diethyl ester 
• 120-13-8 4-ethoxy-3-methoxyphenylacetic acid 
• 79054-44-7 [(E)-1-Dimethylamino-2-(4-methoxy-phenyl)-vinyl]-phosphonic acid diethyl ester 
• 13504-37-5 diethyl phenylacetylphosphonate 
• 33465-33-7 1-Phenyl-2-diethylphosphono-2-dimethylamino-ethylen 
• 79054-54-9 [(E)-1-Hydroxy-2-(4-nitro-phenyl)-vinyl]-phosphonic acid diethyl ester 
• 79054-50-5 ((E)-1-Hydroxy-2-phenyl-vinyl)-phosphonic acid diethyl ester 
• 18855-51-1 Diaethyl-<α-dimethylamino-styryl>-phosphonat 
• 18855-50-0 Diaethyl-<α-dimethylamino-4-nitro-styryl>-phosphonat 

Relevant academic research and scientific papers

Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl-(pyrrolidine-2,2-diyl)bisphosphonate

The optimization of the one-step diphosphorylation reaction is reported. The synthesis of new α-aminobisphosphonates with four- and six-membered rings and acyclic species with several substituents on the nitrogen atom and on the carbon atom bearing the two phosphorus atoms is described.

General and chemoselective bisphosphonylation of secondary and tertiary amides

With Tf2O as the activation reagent, a mild and general method has been developed for the bisphosphonylation of both secondary and tertiary amides. The protocol is highly efficient and chemoselective, and it tolerates a number of sensitive functional groups such as cyano, ester, and aldehyde groups.

PHOSPHORUS FUNCTIONAL ANTIMICROBIAL COATINGS FOR METAL SURFACES

The invention relates to quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds, processes for preparing quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds, antimicrobial coating compositions comprising quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds and method of treating a surface with said compositions to provide a durable, antimicrobial-treated surface.

Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones

A series of azetidin-2-ones substituted at positions 1, 3 and 4 of the azetidinone ring scaffold were synthesised and evaluated for antiproliferative, cytotoxic and tubulin-binding activity. In these compounds, the cis double bond of the vascular targeting agent combretastatin A-4 is replaced with the azetidinone ring in order to enhance the antiproliferative effects displayed by combretastatin A-4 and prevent the cis/trans isomerisation that is associated with inactivation of combretastatin A-4. The series of azetidinones was synthetically accessible via the Staudinger and Reformatsky reactions. Of a diverse range of heterocyclic derivatives, 3-(2-thienyl) analogue 28 and 3-(3-thienyl) analogue 29 displayed the highest potency in human MCF-7 breast cancer cells with IC50 values of 7 nM and 10 nM, respectively, comparable to combretastatin A-4. Compounds from this series also exhibited potent activity in MDA-MB-231 breast cancer cells and in the NCI60 cell line panel. No significant toxicity was observed in normal murine breast epithelial cells. The presence of larger, bulkier groups at the 3-position, for example, 3-naphthyl derivative 21 and 3-benzothienyl derivative 26, resulted in relatively lower antiproliferative activity in the micromolar range. Tubulin-binding studies of 28 (IC50 = 1.37 μM) confirmed that the molecular target of this series of compounds is tubulin. These novel 3-(thienyl) β-lactam antiproliferative agents are useful scaffolds for the development of tubulin-targeting drugs.

Synthesis of the new types of N-substituted aminomethylenebisorganophosphorus acids and their derivatives

The interaction of esters of trivalent organophosphorus acids containing PH and POSiMe3 fragments with various derivatives of formamide is proposed as convenient methods for the synthesis of new N-substituted aminomethylenebisorganophos-phorus acids and their derivatives with three-, four-, and five-coordinated phosphorus. Also the new functionalized derivatives of the new aminomethylenebisphosphinic acids with substituted hydroxymethyl moieties are synthesized, and some properties of the obtained compounds are presented.

NEW TYPES OF AMINOMETHYL ORGANOPHOSPHORUS COMPOUNDS

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.

ZUR SYNTHESE VON BIS-ALKLYLMERCAPTO-METHANPHOSPHONSAEUREDIALKYLESTERN

To find a simple and reproducible synthesis of bis-alkylmercaptomethane phosphonates 1 several methods had been examined.The reaction of chloro-dialkylmercaptomethanes 3 with trialkylphosphite (Method A) and the reaction of diethylmethanphosphonate 8 with mercaptanes (Method F) proved to be the best methods.