2227-43-2

Upstream product

• 64-17-5 ethanol 
• 644-97-3 Dichlorophenylphosphine 
• 1638-86-4 diethyl phenylphosphonite 
• 75-03-6 ethyl iodide 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 1499-22-5 ethylphenylphosphinic chloride 
• 120571-58-6 N-benzyl D-alanine methyl ester 
• 1754-49-0 diethyl phenylphosphonate 

Downstream Products

• 13317-44-7 ethyl(phenyl)phosphinic acid 
• 89438-74-4 (R)-ethylphenyl propylphosphine oxide 
• 61388-07-6 ethylphenyl propylphosphine oxide 
• 76420-34-3 S-methyl ethylphenylphosphinothioate 
• 6829-76-1 ethylphenylphosphinic acid methyl ester 
• 204275-16-1 N-((R)-ethylphenylphosphinyl)-N-benzyl D-alanine methyl ester 
• 204275-15-0 N-((S)-ethylphenylphosphinyl)-N-benzyl D-alanine methyl ester 
• 723296-98-8 (ethyl-phenyl-phosphinoylmethyl)-phosphonic acid diethyl ester 
• 918660-73-8 4-acetylphenyl ethyl(phenyl)phosphinate 
• 1499-22-5 ethylphenylphosphinic chloride 

Relevant academic research and scientific papers

Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery

Several dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.

Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands

A practical synthesis of optically pure alkylphenylvinylphosphine oxides is described, utilizing a nucleophilic displacement at phosphorus to install the vinyl moiety. The products were used to prepare classes of P-stereogenic aminophosphine (PN) and aminohydroxyphosphine (PNO) ligands. Stereocontrol can be exerted at various stages of the synthesis, to provide specific combinations of chirality in the final product. The effect of the stereogenic phosphorus and match-mismatch of chiralities of PNO ligands were examined in the asymmetric ruthenium-catalyzed hydrogen transfer reduction of three aryl ketones.

Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library

An array of 16 enantiomeric pairs of chiral phosphate, phosphonate, and phosphinate esters was used to establish the breadth of the stereoselective discrimination inherent within the bacterial phosphotriesterase and 15 mutant enzymes. For each substrate,

Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement

The taming of the shrew! For the first time, a broadly applicable efficient room-temperature Arbuzov rearrangement is described. This reaction is accomplished through an atom-economical Lewis acid catalyzed process (see scheme, TMSOTf=trimethylsilyl trifluoromethane-sulfonate). The method has been generalized to primary and activated secondary phosphites, phosphinites, and phosphonites.

Trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement

(Matrix presented) We describe a new, straightforward, and easy-to-handle method for achieving an unprecedented trimethylsilyl halide-catalyzed Michaelis-Arbuzov-like rearrangement. This rearrangement occurs at temperatures from room temperature to 80°C and does not require addition of any alkyl halide. The scope and limitations of this new reaction are explored, as well as its mechanism.

PHOSPHINIC ACID AMIDES AS MATRIX METALLOPROTEASE INHIBITORS

The invention provides compounds which are useful as inhibitors of matrix metalloproteases, and which are effective in treating conditions characterized by excess activity of these enzymes. In particular, the present invention relates to a compound having

Enantiomerically pure zinc phosphonates based on mixed phosphonic acid - Phosphine oxide chiral building blocks

The coordination chemistry of enantiomerically pure phosphonic acids H2O3PCH2P(O)(C6H5)(R) [R = CH3 and C2H5] with zinc is described. The structures of two new optical

Design and synthesis of phosphinamide-based hydroxamic acids as inhibitors of matrix metalloproteinases

A new series of hydroxamic acid-based matrix metalloproteinase (MMP) inhibitors containing a unique phosphinamide motif derived from D-amino acid was designed, synthesized, and tested for enzyme inhibition. Compounds with an R configuration at phosphorus

PHOSPHINIC ACID AMIDES AS MATRIX METALLOPROTEASE INHIBITORS

The invention provides compounds which are useful as inhibitors of matrix metalloproteases, and which are effective in treating conditions characterized by excess activity of these enzymes. In particular, the present invention relates to a compound having

An intramolecular Arbuzov rearrangement initiated by anodic oxidation

Dialkyl phenylphosphonite PhP(OR)2 (R = Et, Me) undergoes an intramolecular Arbuzov rearrangement upon electrolysis at an anode in acetonitrile under an oxygen atmosphere to yield alkyl alkylphenylphosphinate PhRP(=O)(OR). The results here suggest that the rearrangement takes place through a radical-chain mechanism initiated by anodic oxidation of the phosphonite to the corresponding cation radical.