5761-97-7Relevant articles and documents
PHOSPHORUS-CONTAINING COMPOUND AND PREPARATION AND USE THEREOF
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Paragraph 0190-0191, (2020/05/14)
The present invention provides a phosphorus-containing compound characterized by being a compound represented by the following structure: the compound is a novel immune cell migration inhibitor. The compound has good hydrophilicity and can be developed into eye drops. The compound has a strong inhibitory ability to immune cell migration and can relieve the symptoms of most dry-eye patients.
Stereoselective Synthesis of P-Stereogenic N-Phosphinyl Compounds
Chelouan, Ahmed,Recio, Roco,lvarez, Eleuterio,Khiar, Noureddine,Fernndez, Inmaculada
supporting information, p. 255 - 259 (2016/02/14)
A number of P-stereogenic N-phosphinyl compounds were stereoselectively prepared in good yields by a straightforward approach, thanks to the diversified and, up until now, unexplored reactivity of (R)- and (S)-dicyclohexylidene-D-glucose methyl phenyl pho
Synthesis of n-butyl ester and n-butylamide of methyl-phenylphosphinic acid: Two case studies
Kiss, Nóra Zsuzsa,Henyecz, Réka,Jablonkai, Erzsébet,Keglevich, Gy?rgy
, p. 766 - 774 (2016/07/06)
n-Butyl methyl-phenylphosphinate and methyl-phenylphosphinic n-butylamide were synthesized by different methods: the reaction of methyl-phenylphosphinic chloride withnBuOH ornBuNH2, respectively, the T3P-promoted derivatiz
Formation of unexpected heterocyclic products from pyrolysis of thiocarbonyl stabilised phosphonium ylides
Aitken, R. Alan,Barker, Graeme,Cleghorn, Lee P.,Reid, Euan J.,Roberts, Sheryl S.
, p. 1135 - 1147 (2014/01/17)
Chiral phthalimido thioxo-stabilised phosphonium ylides, prepared starting from (S)-alanine and (S)-phenylalanine, undergo intramolecular Wittig reaction upon pyrolysis leading to the previously unknown pyrrolo[2,1-a]isoindol-5-one-2- thiones, rather than
Cleavage of P=O in the presence of P-N: Aminophosphine oxide reduction with in situ boronation of the PIII product
Kenny, Niall P.,Rajendran, Kamalraj V.,Jennings, Elizabeth V.,Gilheany, Declan G.
supporting information, p. 14210 - 14214 (2013/11/06)
In contrast to tertiary phos-phine oxides, the deoxygenation of aminophosphine oxides is effectively impossible due to the need to break the immensely strong and inert P=O bond in the presence of a relatively weak and more reactive P-N bond. This long-sta
Enzymatic synthesis of enantiopure precursors of chiral bidentate and tridentate phosphorus catalysts
Kaczmarczyk, Sylwia,Kwiatkowska, Malgorzata,Madalinska, Lidia,Barbachowska, Agnieszka,Rachwalski, Michal,Blaszczyk, Jaroslaw,Sieron, Leslaw,Kielbasinski, Piotr
supporting information; experimental part, p. 2446 - 2454 (2011/11/04)
The Candida antarctica lipase (CAL-B)-catalyzed acetylation of racemic 2-hydroxymethylphenyl(methyl)phenylphosphine oxide, performed in diethyl ether, led to kinetic resolution with an unusually high enantioselectivity (E=3000). The CAL-B-mediated desymme
Enantioselective preparation of P-chiral phosphine oxides
Adams, Harry,Collins, Rebecca C.,Jones, Simon,Warner, Christopher J. A.
supporting information; experimental part, p. 6576 - 6579 (2012/01/15)
A highly efficient chiral auxiliary-based strategy for the asymmetric synthesis of P-chiral phosphine oxides in >98:2 er has been developed. The methodology involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides.
Synthesis of P-stereogenic phosphorus compounds. Asymmetric oxidation of phosphines under appel conditions
Bergin, Enda,O'Connor, Cormac T.,Robinson, Shane B.,McGarrigle, Eoghan M.,O'Mahony, Colm P.,Gilheany, Declan G.
, p. 9566 - 9567 (2008/02/13)
Racemic phosphines are converted into enantioenriched phosphine oxides via a synthetically simple, but theoretically interesting, oxidation procedure in good enantiomeric excess (up to 80%) and excellent yields (>95%). These phosphine oxides can be oxidatively coupled to provide easy access to enantiopure DiPAMPO analogues. Particularly attractive aspects of this procedure are the operational simplicity and the low cost required to synthesize these high value compounds. Copyright
Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands
Oliana, Marco,King, Frank,Horton, Peter N.,Hursthouse,Hii, King Kuok
, p. 2472 - 2479 (2007/10/03)
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.
Catalysis of the ethanolysis of aryl methyl phenyl phosphinate esters by alkali metal ions: Transition state structures for uncatalyzed and metal ion-catalyzed reactions
Onyido, Ikenna,Albright, Kendall,Buncel, Erwin
, p. 1468 - 1475 (2007/10/03)
This paper reports on a spectrophotometric kinetic study of the effects of the alkali metal ions Li+ and K+ on the ethanolysis of the aryl methyl phenyl phosphinate esters 3a-f in anhydrous ethanol at 25°C. Rate data obtained in the absence and presence of complexing agents afford the second-order rate constants for the reaction of free ethoxide (kEtO-) and metal ion-ethoxide ion pairs (kMOEt). The sequence k EtO- MOEt is established for all the substrates, contrary to the generally observed reactivity order in nucleophilic substitution processes. The quantities δGip, δGts and ΔGcat, which quantify the observed alkali metal ion effect in terms of transition state stabilization through chelation of the metal ion, give the order δGts > δGip for Li+ and K+. Hammett plots show significantly better correlation of rates with σ and σo substituent constants than with σ-, yielding moderately large Ρ(Ρo) values that are consistent with a stepwise mechanism in which formation of a pentacoordinate (phosphorane) intermediate is the rate-limiting step. The range of the values of the selectivity parameter, Ρn (= Ρ/Ρeq), 1.3 1.6, obtained for the uncatalyzed and alkali metal ion catalyzed reactions indicates that there is no significant perturbation of the transition state (TS) structure upon chelation of the metal ions. This finding is relevant to the mechanism of enzymatic phosphoryl transfer involving metal ion co-factors. The present results enable one to compare structural effects for nucleophilic reactions of several series of organophosphorus substrates. It is shown that the order of reactivity of the substrates: 4-nitrophenyl dimethyl phosphinate (2) > 3a > 4-nitrophenyl diphenyl phosphinate (1) is determined mainly by the steric effects of the alkyl/aryl substituents around the central P atom in the TS of the reaction. The Royal Society of Chemistry 2005.
