50917-73-2

Usage

Uses

Used in Pharmaceutical Synthesis:
DIETHYL-N-BENZYLIDENEAMINOMETHYLPHOSPHONATE is used as a synthetic reagent for the preparation of β-lactams, which are important components in the structure of numerous antibiotics, such as penicillins and cephalosporins. Its application in this field is crucial for the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Organic Chemistry:
DIETHYL-N-BENZYLIDENEAMINOMETHYLPHOSPHONATE is used as a synthetic building block for the preparation of α-aminophosphonic acids. These compounds are structural analogs of amino acids and have potential applications in the development of new pharmaceuticals, agrochemicals, and chiral catalysts.
Used in the Formation of Quaternary Carbons:
DIETHYL-N-BENZYLIDENEAMINOMETHYLPHOSPHONATE is used as a key intermediate for the formation of quaternary carbon centers in organic molecules. The formation of quaternary carbons is essential in the synthesis of complex organic compounds, including natural products and biologically active molecules, which can be used in various industries such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C12H18NO3P/c1-3-15-17(14,16-4-2)11-13-10-12-8-6-5-7-9-12/h5-10H,3-4,11H2,1-2H3

Upstream product

• 50917-72-1 aminomethylphosphonic acid diethyl ester 
• 100-52-7 benzaldehyde 
• 50917-84-5 diethyl N-benzylaminomethylphosphonate hydrochloride 
• 17982-55-7 diethyl (azidomethyl)phosphonate 
• 94807-27-9 O,O-diethyl N,N-bis(trimethylsilyl)aminomethylphosphonate 

Downstream Products

• 64244-35-5 Cyclohexylidenemethyl-[1-phenyl-meth-(E)-ylidene]-amine 
• 64244-33-3 [1-Phenyl-meth-(E)-ylidene]-((E)-styryl)-amine 
• 67257-50-5 (1-{[1-Phenyl-meth-(E)-ylidene]-amino}-butyl)-phosphonic acid diethyl ester 
• 50917-75-4 (Diethoxy-phosphoryl)-{[1-phenyl-meth-(E)-ylidene]-amino}-acetic acid methyl ester 
• 64244-34-4 N-benzylidene methyl-2 styrylamine 
• 343221-98-7 [1-Phenyl-meth-(Z)-ylidene]-[3,5,5-trimethyl-cyclohex-2-en-(Z)-ylidenemethyl]-amine 
• 108071-05-2 ((E)-Oct-1-enyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 130829-09-3 (2-Biphenyl-4-yl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-ethyl)-phosphonic acid diethyl ester 
• 130828-85-2 (2-(4-Iodo-phenyl)-1-{[1-phenyl-meth-(E)-ylidene]-amino}-ethyl)-phosphonic acid diethyl ester 
• 130828-98-7 (2-(2-Methoxy-phenyl)-1-{[1-phenyl-meth-(E)-ylidene]-amino}-ethyl)-phosphonic acid diethyl ester 
• 130829-01-5 [1-{[1-Phenyl-meth-(E)-ylidene]-amino}-2-(4-trimethylsilanyl-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 130829-00-4 [1-{[1-Phenyl-meth-(E)-ylidene]-amino}-2-(3-trimethylsilanyl-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 130828-99-8 [1-{[1-Phenyl-meth-(E)-ylidene]-amino}-2-(2-trimethylsilanyl-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 130829-04-8 (2-(2,4-Difluoro-phenyl)-1-{[1-phenyl-meth-(E)-ylidene]-amino}-ethyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Cyclic ketones in spiroannulation

Conversion of a cyclic carbonyl carbon into a quaternary carbon has been effected by a Wittig-Horner reaction with diethyl (N-benzyliden) aminomethylphosphonate and a subsequent alkylation with a protected vinyl ketone. The product was a substrate for spiroannulation after initial hydrolysis. The reaction sequence was carried out as a one-pot reaction. Copyright Taylor & Francis Group, LLC.

Phosphorous acid analogs of novel P2-P4 macrocycles as inhibitors of HCV-NS3 protease

HCV-NS3 protease is essential for viral replication and NS3 protease inhibitors have shown proof of concept in clinical trials. Novel P2-P4 macrocycle inhibitors of NS3/4A comprising a P1 C-terminal carboxylic acid have recently been disclosed. A series o

Synthesis of diethyl α-(o-nitroaryl)phosphoglycines via oxidative nucleophilic substitution of hydrogen in nitroarenes

The carbanion of protected diethyl phosphoglycinate adds to nitroarenes in liquid ammonia in ortho position to the nitro group. Subsequent oxidation of the resulting adduct σH with potassium permanganate gave N-protected diethyl α-(o-nitroaryl)phosphoglycinates. Georg Thieme Verlag Stuttgart New York.

1-Azidoalkylphosphonates - A convenient substrates for the synthesis of N-alkyl α-aminoalkylphosphonates

Diethyl [1-(alkylamino)alkyl]phosphonates 5 have been efficiently synthesized via a two-step reaction of diethyl 1-azidoalkylphosphonates 1 with triphenylphosphine, followed by in situ transformation of thus formed phosphazenes 2 into imines 4 by means of

1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: Synthesis of derivatives of 2′,5′-dihydro-1′H-pyrrolo[3′,4′:1,2][60]fullerene

Imines 1 have been prepared by the condensation of benzaldehyde and corresponding primary amines in which the ester group, phosphonate ester group and depsipeptide are introduced. [60]Fullerene reacts with imines 1 to give the corresponding isomers of fullerene-fused proline derivatives 2 via a process of 1,3-dipolar cycloaddition. 1,3,5-Tris(ethoxycarbonylmethyl)perhydro-1,3,5-triazine 4, which has been prepared by the condensation of ethyl glycinate with paraformaldehyde, depolymerizes thermally to provide an azomethine ylide which reacts with [60]fullerene to afford ethyl 2′,5′-dihydro-1′H-pyrrolo-[3′,4′:1,2][60] fullerene-2′-carboxylate 5. 2-Phenyl-4,5-dihydrooxazol-5-one 6 tautomerizes thermally to form the mesoionic oxazolium 5-oxide 6a, which then, as a cyclic azomethine ylide, combines further with [60]fullerene to give 5′-phenyl-2′H-pyrrolo[3′,4′:1,2][60]fullerene 7 which possesses Cs symmetry.

On the stereochemical purity of (+)-7-aminocephalosporanic acid

(±)-7-Aminocephalosporanic acid (18a) and (±)-7-epi- aminocephalosporanic acid (4a) have been synthesized. A chiral HPLC method has been developed for the separation of the four stereo-isomers. Natural (+)-7-aminocephalosporanic acid (1) was demonstrated to he enantiomerically (ee >> 99.95%) and diastereomerically (de >>99.95%) pure.

α-Aminophosphonates. III. Cycloaddition anionique-1,3 des esters α,β-insatures: Preparation et transformations des Δ1-pyrrolines

The anions of the 2-azaallylphosphonates 1 react with the α,β-unsaturated esters 2 to yield intermediates 4'.These intermediates form the 2-diethoxyphosphonyl-4-ethoxycarbonylpyrrolidines 4 following a protonation while an elimination of the anion of the

PO-Activated Olefination and Conversion of Aldehydes and Ketones to Higher Amines; II. Synthesis of Arylethylamines

The transformation of arylcarboxaldehydes and/or - ketones 2 by three different routes into arylethylamines 3 and/or 4 is reported.According to the first route, the intermediate iminophosphonates 9 react through a classical PO-activated olefination.The second and the third involve the rearrangement of the iminophosphonates 9 into the vinylphosphoramidates 12.

A CONVENIENT SYNTHETIC METHOD FOR SCHIFF BASES. THE TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE-CATALYZED REACTION OF N,N-BIS(TRIMETHYLSILYL)AMINES WITH ALDEHYDES AND KETONES

N,N-Bis(trimethylsilyl)amines react with aldehydes or ketones in the presence of trimethylsilyl trifluoromethanesulfonate to give Schiff bases in high yields.In situ utilization of the reaction solution as the Schiff base is also demonstrated.