29668-61-9

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL (1-CYANOETHYL)PHOSPHONATE is used as an intermediate in the synthesis of 4-(1-Cyanoethyl)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (C979545), a compound derived from the crude extract of Citrullus colocynthis. This extract has been studied for its antifungal activity against various plant pathogenic fungi, indicating potential applications in the development of antifungal agents.
Used in Polymer Industry:
DIETHYL (1-CYANOETHYL)PHOSPHONATE is used as an oligomeric product in the thermal polymerization of the acrylonitrile/styrene system. Its presence in this system contributes to the formation of polymers with specific properties, making it a valuable component in the synthesis of various polymer materials.

InChI:InChI=1/C7H14NO3P/c1-4-10-12(9,11-5-2)7(3)6-8/h7H,4-5H2,1-3H3

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 107-12-0 propiononitrile 
• 74-88-4 methyl iodide 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 122-52-1 triethyl phosphite 
• 19481-82-4 2-bromopropionitrile 

Downstream Products

• 60727-74-4 2-[3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile 
• 60727-74-4 2-[(8R,9S,13S,14S)-3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile 
• 60727-73-3 3β-t-Butoxy-20-carbonitrilpregna-5,17(20)-dien 
• 63089-63-4 1-(α-Cyanoaethyliden)-4-t-butylcyclohexan 
• 87184-46-1 2-[2-Isopropyl-cyclopent-(Z)-ylidene]-propionitrile 
• 219692-69-0 2-diethylphosphono-2-phenylsulfinylpropionitrile 
• 454442-08-1 3-[3-(1-cyano-ethylidene)-cyclohex-1-enyl]-2-methyl-acrylonitrile 
• 454442-10-5 3-[3-(cyano-ethylidene)-cyclohex-1-enyl]-2-methyl-acrylic acid ethyl ester 
• 53153-76-7 2-cyclohexylidenepropanenitrile 
• 320783-60-6 diethyl (1-cyano-1-methyl-5-phenylpentyl)phosphonate 
• 524943-14-4 2-(3,3,5,5-Tetramethylcyclohexylidene)propionitrile 
• 596136-34-4 N-[[(5S)-3-[3-fluoro-4-(4-cyanomethylidene-piperidinyl)-phenyl]-2-oxo-5-oxazolidinyl]-methyl]-acetamide 

Relevant academic research and scientific papers

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

Application of Dually Activated Michael Acceptor to the Rational Design of Reversible Covalent Inhibitor for Enterovirus 71 3C Protease

Targeted covalent inhibitors (TCIs) have attracted growing attention from the pharmaceutical industry in recent decades because they have potential advantages in terms of efficacy, selectivity, and safety. TCIs have recently evolved into a new version with reversibility that can be systematically modulated. This feature may diminish the risk of haptenization and help optimize the drug-target residence time as needed. The enteroviral 3C protease (3Cpro) is a valuable therapeutic target, but the development of 3Cpro inhibitors is far from satisfactory. Therefore, we aimed to apply a reversible TCI approach to the design of novel 3Cpro inhibitors. The introduction of various substituents onto the α-carbon of classical Michael acceptors yielded inhibitors bearing several classes of warheads. Using steady-state kinetics and biomolecular mass spectrometry, we confirmed the mode of reversible covalent inhibition and elucidated the mechanism by which the potency and reversibility were affected by electronic and steric factors. This research produced several potent inhibitors with good selectivity and suitable reversibility; moreover, it validated the reversible TCI approach in the field of viral infection, suggesting broader applications in the design of reversible covalent inhibitors for other proteases.

Backbone modification of retinal induces protein-like excited state dynamics in solution

The drastically different reactivity of the retinal chromophore in solution compared to the protein environment is poorly understood. Here, we show that the addition of a methyl group to the C=C backbone of all-trans retinal protonated Schiff base acceler

Synthesis and chemical reactions of 1-cyano-1- isocyanoalkylphosphonic acid esters

1-Cyano-1-isocyanoalkylphosphonic acid esters 4 were synthesized starting from cyanoalkyl-phosphonic acid esters 1 by amination and formylation followed by dehydration with trichloromethylchloroformate (diphosgene) and triethylamine at low temperatures. B

Carbanionic displacement reactions at phosphorus. Part III.1 Cyanomethylphosphonate vs. cyanomethylenediphosphonate. Synthesis and solid-state structures

The results of the carbanionic reaction between acetonitrile and chlorophosphates depend strongly on the nature of the metallating agent (LiTMP, LDA, LiHMDS). According to the nature of the base, the reaction can be directed towards the formation of either cyanomethylphosphonates 3 or cyanomethylenediphosphonates 5. Electrophilic halogenation of lithiated cyanomethylphosphonate 2a leads to the mono-chloro 17, -bromo 18 and -iodo 19 derivatives. Only the monochloro product 17 is stable enough to be isolated in pure form. The structures of cyanobenzylphosphonate 10b, cyanomethylenediphosphonate 5b and its corresponding lithiated carbanion 4b are determined by X-ray crystallography. The polymeric structure, coupled with a wide charge delocalization, without C-Li contacts, is in agreement with the lack of reactivity towards electrophiles. The Royal Society of Chemistry 2000.

Rhodium-catalyzed enantioselective Michael addition of (1-cyanoethyl)phosphonate: Synthesis of optically active phosphonic acid derivatives with phosphorus-substituted quaternary asymmetric carbon center

Asymmetric Michael addition of diethyl (1-cyanoethyl)phosphonate with vinyl ketones or acrylaldehyde in the presence of 0.01 molar amount of a rhodium catalyst prepared in situ from Rh(acac)(CO)2 and a trans-chelating chiral diphosphine ligand

Cycloaddition of N-Buta-1,3-dienyl-succinimide to gem-Substituted Vinyl Phosphonates

N-Buta-1,3-dienylsuccinimide 3 reacted with trimethyl 2-phosphonoacrylate 4, triethyl 2-phosphonoacrylate 5, α-(diethylphosphono)acrylonitrile 6, α-(diethylphosphono)vinyl methylsulfone 7 and tetraethyl ethenylidene bis(phosphonate) 8 to give the ortho-cy

A short and versatile synthesis of 3-substituted 2-aminoquinolines

A short and versatile synthesis of a series of 3-substituted 2-aminoquinolines was accomplished in good yields starting from 2-nitrobenzaldehyde. Organic phosphonates were used as key synthetic intermediates and in some cases amino acids as readily available starting materials. The final two key steps of the sequence involving a reduction and ring closure that led to the 2-aminoquinoline skeleton were carried out in a 'one pot' procedure using SnCL22H2O.

One-step Synthesis of Stabilized Phosphonates

Phosphonates possessing α-electron withdrawing functionalities can be readily prepared by treatment of nitriles, nitroalkanes, and esters with 2 molar equivalents of base followed by phosphonylation with diethyl chlorophosphate.