10123-62-3

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for the synthesis of lipophilic oxoamides with activity against phospholipase A2. These compounds have potential applications in the development of anti-inflammatory and analgesic drugs.
Used in Enzyme Inhibition:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for the synthesis of triose phosphate isomerase of muscle inhibitors. These inhibitors can be employed in the study of enzyme function and the development of therapeutic agents for muscle-related disorders.
Used in Chemical Research:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for heteroatom-directed alkyl cyanation of alkynes, which is a significant method in organic chemistry for the formation of various complex molecules.
Used in Analytical Chemistry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a fluorescent substrate for carbon-phosphorous lyase, an enzyme involved in the degradation of organophosphorus compounds. This application aids in the study of enzyme activity and the development of detection methods for these compounds.
Used in Microwave-Assisted Chemistry:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used in microwave-assisted cleavage of phosphate, phosphonate, and phorphoramide esters. This technique allows for faster and more efficient cleavage reactions, which can be beneficial in various chemical synthesis processes.
Used in Antiviral Drug Synthesis:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for amination and stereoselective olefination in the synthesis of HIV-1 antivirals. These compounds have the potential to be developed into effective treatments for HIV and AIDS.
Used in Organic Synthesis:
DIETHYL (2-CYANOETHYL)PHOSPHONATE 95 is used as a reactant for base-catalyzed stereospecific anti-Markovnikov addition reactants. This reaction is an important method in organic chemistry for the synthesis of various organic compounds with specific stereochemistry.

InChI:InChI=1/C7H14NO3P/c1-3-10-12(9,11-4-2)7-5-6-8/h3-5,7H2,1-2H3

Upstream product

• 2303-76-6 sodium diethyl phosphite 
• 107-13-1 acrylonitrile 
• 762-04-9 phosphonic acid diethyl ester 
• 762-04-9 Diethyl phosphonate 
• 79-06-1 2-propenamide 
• 1738-25-6 3-dimethylaminopropiononitrile 
• 122-52-1 triethyl phosphite 
• 542-76-7 3-Chloropropionitrile 
• 934538-82-6 thiophosphoric acid S-[2-(2-bromo-phenyl)-ethyl] ester O,O'-diethyl ester 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 2417-90-5 bromopropionitrile 
• 36240-50-3 diethyl 2-cyano-2-trimethylsilylethanephosphonate 
• 4554-16-9 2,3-dibromopropionitrile 
• 94627-35-7 1-(2-cyano-ethyl)-1-methyl-piperidinium; iodide 

Downstream Products

• 914386-20-2 (Z)-3-(4-Fluoro-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile 
• 113811-57-7 diethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 
• 113811-51-1 monoethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 
• 1777-22-6 1-(diethoxyphosphinyl)-3-hexanone 
• 69549-53-7 α-Amino-γ-diaethylphosphonopropyliden>-α,α-diphosphonsaeure 
• 4402-24-8 diethyl 3-aminopropan-1-ylphosphonate 
• 5962-42-5 3-phosphonopropionic acid 

Relevant academic research and scientific papers

New inhibitors of rabbit muscle triose-phosphate isomerase

We describe the synthesis and evaluation of three new competitive inhibitors of triose-phosphate isomerase. One of them (phosphoglycoloamidoxime: Ki = 4.5 μM) is among the best reversible inhibitors so far reported for this enzyme.

Radical cyanomethylation via vinyl azide cascade-fragmentation

Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.

Stereodefined dinucleoside (3′,5′)-propionamidophosphonates and β-cyanoethylphosphonates and their incorporation into modified oligonucleotides

Base-catalyzed stereospecific anti-Markovnikov addition of dinucleoside (3′,5′)-H-phosphonates to the activated alkenes acrylamide and acrylonitrile resulting in the synthesis of P-chiral diastereomerically pure dinucleoside (3′,5′)-alkylphosphonates is reported.

Comparison of catalytic activity of hexamethyltriamino- and tri-n-butylphosphines in the Pudovik reaction

The catalytic activity of hexamethyltriaminophosphine in the P(O)–H bond addition to electron-deficient alkenes was studied. Depending on the nature of the alkene, hexamethyltriaminophosphine produces better or lower yields of the reaction products compared to tri-n-butylphosphine.

Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid

Using an N-oleoyl ethanolamide scaffold, a series of phosphate polar head group analogues of LPA comprised of various α-substituted phosphonates and thiophosphates was prepared. In a broken cell GTP[γ35S] binding assay, agonist activity was evaluated at the three LPA receptors of the endothelial differentiation gene (Edg) family. This study has resulted in the discovery of a nonhydrolyzable LPA1-selective agonist (11). Additionally, thiophosphate 19 bears an isosteric phosphate mimetic that confers agonism at the LPA1 receptor but not LPA2.

ACTIVATION ANIONIQUE DU PHOSPHITE DE DIETHYLE PAR LE FLUORURE DE POTASSIUM DEPOSE SUR ALUMINE, SYNTHESE DE PHOSPHONATES FONCTIONALISES

Dry reactions of diethylphosphite on KF-AL2O3 with different electrophiles conduct to the synthesis of functionalized phosphonates.

REACTION OF α-CYANOACRYLIC ACID AND CYANOACRYLATES WITH DIALKYL AND DIARYL PHOSPHITES

α-Cyanoacrylic acid and α-cyanoacrylates add dialkyl and diaryl phosphites and diethyl thiophosphite at the C=C double bond in the absence of catalyst.This is an anti-Markpvnikov reaction, which yields the corresponding phosphonates and thiophosphonates. Keywords: alkenes, hydrophosphorylation, addition reaction, thiophosphites, thiophosphonates, phosphites, phosphonates, cyanoacrylic acid.

Tetramethylguanidine (TMG)-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes, ketones and imines

Tetramethylguanidine-catalyzed addition of dialkyl phosphites to α,β- unsaturated carbonyl compounds, alkenenitriles, aldehydes and ketones constitutes a practical route to a variety of phosphonate synthons. The very mild conditions employed, together with the short reaction times, make the procedure highly versatile and tolerant to a range of functionalities. The proposed methodology is also convenient for the preparation of α- aminophosphonates.

Me3P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts

Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes

PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78-85%) in all cases. The protocol was also extended with good results to α,β-unsaturated esters and nitriles. This demonstrates that PS-BEMP is a good catalyst for the phospha-Michael addition to electron-poor alkenes.