Phenyl methylphosphonic acid

Methyl phenyl sulfone Methylphosphonic acid 2-Methylpropanal 2-Methylpropane 2-Methyl-1 -propanethiol 2-Methyl-2-propanethiol Ht, 0.972 at-121.6°C ... 

Phosphonothioic acid, methyl-, (5-ethyl-2-methyl-1,3,2-dioxaphorinan-5-yl) methyl methyl ester, p-oxide. See Methylphosphonic acid, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester Phosphonous acid, (1,1 -biphenyl)-4,4 -diylbis-, tetrakis (2,4-bis (1,1-dimethylethyl) phenyl) ester. See Tetrakis (2,4-di-t-butylphenyl)-4,4 -biphenylenediphosphonite Phosphopyridoxal. See Pyridoxal 5-phosphate Phosphoramidic acid diethyl ester. See Mephosfolan... 

Optically active substituted benzylphosphonates lA, IE and IF could be prepared by the condensation of substituted phenoxyacetyl chlorides MS and optically pure l-hydroxy(substituted phenyl)methylphosphonates M2 (Scheme 6.10). Substituted phenoxyacetyl chlorides MS could be easily synthesized starting from substituted phenols and bromoacetic acid ester [24, 77]. Optically active l-hydroxy(substituted... 

It was found that optically active 1-hydroxyaIkylphosphonates were easily racemized in strong base or acid medium. Therefore a Schotten-Baumann condition was chosen for the condensation of optically active 1-hydroxy (substituted phenyl) methylphosphonates and substituted phenoxyacefyl chlorides. 

We also observed that target compounds lA, IE and IF containing carboxylic acid ester bonds were sensitive to acid, base or water, especially at higher temperatures. The preparation of optically active lA, IE, and IF required a control of moderate temperature, all reagents and solvents in this reaction needed to be pre-processed in anhydrous state. The preparation of optically active lA, IE and IF was carried out in three stages. First, a solution of substituted phenoxyacefyl chloride MS was added dropwise to the solution of optically active 1-hydroxy (substituted phenyl)methylphosphonates M2 under 5 °C Secondly, the reaction solution was stirred at room temperature for 2-4 h, and then for another 1-2 h at 40 °C under mild reaction conditions. In such a way, optically active lA, IE and IF could be conveniently obtained in good yield, and the ee value of enantiomers had no obvious decline compared with the ee value of M2. 

General procedure A solution of an appropriate substituted phenoxyacetyl chloride (22 mmol) in trichloromethane (10 mL) was added to a stirred mixture of corresponding optically active (9,(9-dimethyl 1-hydroxy-1-(substituted phenyl) methylphosphonate (20 mmol) and pyridine or triethylamine (22 mmol) in trichloromethane (25 mL) at 10-25 °C. The resultant mixture was stirred for 3-5 h at room temperarnre, and then for 1-2 h at 40-42 °C. The trichloromethane layer was washed with 0.1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and concentrated. The residue was purified by column chromatography on silica gel and eluted with petroleum ether/acetone (2/1, v/v) to give the corresponding (9,(9-dimethyl [1-(substituted phenoxyacetoxy)- -(substituted phenyl)]methylphosphonate IE or IF. Optically active (9,(9-diethyl [1-(substituted phenoxyacetoxy)-(-(substituted phenyl)]methylphosphonate lA could be synthesized by a similar procedure. Series of optically active lA, IE, and IF were obtained as the yellow liquids or colorless crystals in 52-89 % yields. The enantiomeric excesses (ee) were determined by HPLC analysis on a chiral DAICEL CHIRALPAK AS-H column at 254 nm or 230 nm, n-hexane/f-PrOH = 70/30. 

Phenyl(phenylamino)]methylphosphonic acid Mono-octyl ester, in P-00155... 

Phenylazo)-1,2,3-benzenetriol, P-00092 Phenylazoxine S, P-00101 [Phenyl(phenylamino)]methylphosphonic acid Mono-octyl ester, in P-00155... 

The reaction of diphenyl methylphosphonate with lithium alkoxides gives phenyl alkyl methylphosphonates even with hindered alcohols and, in the case of chiral alcohols, with high diastereoselectivity at phosphorus. [Hydroxy(pho-sphoryloxy)X, iodo]benzenes 289, prepared from reactions of iodosobenzene with phosphonic or phosphinic acids react with ketones, esters or phenyl acetylene to give esters 290. Racemic l-hydroxy-4-(3-phenoxyphenyl)butylphosphonate diethyl ester undergoes stereoselective acetylation in the presence of a lipase to... 

DL-a-acetamido-P-hydroxy-p-nitropropiophenone has been prepared from L-(+)-threo-(p-nitrophenyl)-2-aminopropan-l,3-diol and acetic anhydride followed by photooxidation in the presence of acidic KBrOs and HBr. Photosensitized electron transfer reactions of tri-1-naphthyl phosphate and di-1-naphthyl methyl phosphate using 9,10-dicyanoanthracene are reported to lead to the formation of 1,1 -binaphthyl, but no reaction occurs for mono-1-naphthyl and di- or tri-phenyl esters. Irradiation of bis(3,4-methylenedioxyphenyl) methylphosphonate in the presence of DCA induces single electron oxidation followed by intramolecular rearrangement and gives 2-(3,4-methylenedioxyphenyl)-3,4-methylenedioxy-phenyl methylphosponate. ... 

Anilinesulfonephthalein, A-00369 Propyl hydrogen methylphosphonate, in M-00244 2-Phenyl-4-quinolinecarboxylic acid Me ester, in P-00189... 

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