33973-48-7

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 1-PHENYLETHYL PHOSPHONATE is used as a reactant for the carbanion oxidative nucleophilic substitution of hydrogen. This reaction is crucial in the synthesis of various pharmaceutical compounds, as it allows for the selective replacement of hydrogen atoms with other functional groups, leading to the formation of new and potentially bioactive molecules.
Used in Chemical Synthesis:
In the field of chemical synthesis, DIETHYL 1-PHENYLETHYL PHOSPHONATE is used as a reactant for base-catalyzed olefination. This process involves the formation of carbon-carbon double bonds, which are essential structural elements in many organic compounds, including natural products, pharmaceuticals, and materials. The use of DIETHYL 1-PHENYLETHYL PHOSPHONATE in this reaction allows for the efficient and selective formation of these double bonds, facilitating the synthesis of a wide range of organic compounds.
Overall, DIETHYL 1-PHENYLETHYL PHOSPHONATE is a valuable reagent in both the pharmaceutical and chemical synthesis industries, enabling the creation of new and potentially useful compounds through its involvement in key chemical reactions.

InChI:InChI=1/C12H19O3P/c1-4-14-16(13,15-5-2)11(3)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

Upstream product

• 585-71-7 (1-bromoethyl)benzne 
• 122-52-1 triethyl phosphite 
• 51346-81-7 (1,1-dichloro-ethyl)-phosphonic acid diethyl ester 
• 23402-69-9 lithium diphenylcuprate 
• 591-51-5 phenyllithium 
• 25944-64-3 diethyl (1-phenylethenyl)phosphonate 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 74-88-4 methyl iodide 
• 98-85-1 1-Phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 1459-14-9 (R)-(1-bromoethyl)benzene 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 762-04-9 phosphonic acid diethyl ester 
• 98-86-2 acetophenone 

Downstream Products

• 61470-40-4 1-phenylethylphosphonic acid 
• 115050-50-5 diethyl 1-(4-nitrophenyl)ethylphosphonate 
• 1043498-97-0 (S)-2,2-dimethyl-4-((E)-2-phenylpropenyl)oxazolidine-3-carboxylic acid tert-butyl ester 
• 1149343-96-3 diethyl α-(2-fluoro-4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-94-1 diethyl α-(4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-97-4 diethyl α-(3-chloro-4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-95-2 diethyl α-(3-fluoro-4-nitrophenyl)-α-methylbenzylphosphonate 
• 1205638-06-7 (4S)-2,2-dimethyl-4-((E)-3-phenyl-but-2-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1403670-09-6 (Z)-5-(3-methoxyphenyl)-2-phenyl-2-pentene 
• 1393114-13-0 (E)-5-(3-methoxyphenyl)-2-phenyl-2-pentene 
• 1403670-58-5 (Z)-5-(2-methoxyphenyl)-2-phenyl-2-pentene 
• 1393114-15-2 (E)-5-(2-methoxyphenyl)-2-phenyl-2-pentene 
• 1403670-90-5 (Z)-5-(3-chlorophenyl)-2-phenyl-2-pentene 
• 1393114-17-4 (E)-5-(3-chlorophenyl)-2-phenyl-2-pentene 

Relevant academic research and scientific papers

Catalytic synthesis of 1-arylethylphosphonates by the hydrogenation of unsaturated precursors in the presence of chitosan-based palladium catalysts

Three-component silica-supported palladium-containing systems based on chitosan were synthesized and studied by scanning electron microscopy. These systems showed catalytic activity in the hydrogenation (including chemoselective hydrogenation) of α,β-unsa

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

Preparation method of large-steric-hindrance alkyl substituted phosphite diester

The invention discloses a preparation method of large-steric-hindrance alkyl substituted phosphite diester, and relates to a novel method for preparing the large-steric-hindrance alkyl substituted phosphite diester compound which is difficult to synthesiz

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

Efficient synthesis of α-substituted ethylphosphonates via CuH-catalyzed conjugate reduction of terminal alkenylphosphonate

An unprecedented approach toward synthesis of α-substituted ethylphosphonates based on CuH-catalyzed conjugate reduction of vinylphosphonates has been successfully developed. This protocol features mild conditions, broad substrate scope, good functional group compatibility, high overall efficiencies, and easy gram-scale synthesis. The Cu-catalyzed reduction takes place in a highly selective manner on the phosphono substituted C[dbnd]C bond in the case of the reaction of alkenylphosphonates bearing both phosphono and alkyl or aryl substituted alkene moieties. Furthermore, the result of competitive reaction indicates that the Cu-catalyzed conjugate reduction of vinylphosphonate is more challenging and reproducible than the corresponding acrylate's reaction.

Metal-free diimide reduction of alkenylphosphonates: simple and efficient protocol for the synthesis of α-substituted ethylphosphonates

A simple and straightforward method for the synthesis of α-substituted ethylphosphonates via diimide reduction strategy is described. With K3PO4 or Na2CO3 as the basic additive, a range of terminal alkenylphosph

Applications of α-phosphonovinyl tosylates in the synthesis of α-arylethenylphosphonates via suzuki-miyaura cross-coupling reactions

It has been demonstrated for the first time that α-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access α-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.

Asymmetric hydrogenation of diethyl 1-phenylvinylphosphonate by metal complexes in CH2Cl2 and in supercritical carbon dioxide using phosphite-type ligands

Asymmetric hydrogenation of diethyl 1-phenylvinylphosphonate was carried out for the first time in dichloromethane and supercritical carbon dioxide in the presence of phosphite and amidophosphite ligands. The catalysts based on [Ir(COD)2]BARF (COD is 1,5-

Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.