63314-88-5

Usage

InChI:InChI=1/C4H9O2P/c1-4-7(3,5)6-2/h4H,1H2,2-3H3

Upstream product

• 1066-52-0 methyl methylphosphonochloridate 
• 1826-67-1 vinyl magnesium bromide 
• 3743-07-5 dimethyl chlorophosphite 
• 1066-50-8 Ethylphosphonic dichloride 
• 63578-38-1 dimethyl vinylphosphonite 
• 106-95-6 allyl bromide 

Downstream Products

• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 
• 87647-63-0 4-(Methoxy-methyl-phosphinoyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid ethyl ester 
• 139574-95-1 2-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 35597-44-5 L-phosphinothricin 
• 73679-07-9 (S)-(+)-phosphinothricin 
• 125674-33-1 Methyl 3-(4-methoxyphenyl)-2-isoxazolin-5-yl(P-methyl)phosphinate 
• 125674-43-3 Methyl 3-benzyl-2-isoxazolin-5-yl(P-methyl)phosphinate 
• 139575-01-2 2-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 139574-94-0 methyl 2-(benzylideneamino)-4-(methoxymethylphosphinyl)butyrate 
• 89222-22-0 2-(Benzyl-methyl-amino)-2-[2-(ethoxy-methyl-phosphinoyl)-ethyl]-malonic acid diethyl ester 
• 89222-23-1 2-(3-Chloro-4-methyl-phenylamino)-2-[2-(ethoxy-methyl-phosphinoyl)-ethyl]-malonic acid diethyl ester 

Relevant academic research and scientific papers

Asymmetric Synthesis of (+)-Phosphinothricin and Related Compounds by the Michael Addition of Glycine Schiff Bases to Vinyl Compounds

(S)-(+)-Phosphinothricin was prepared in good optical yield by th Michael addition of chiral glycine Schiff base derived from (S)-2-hydroxy-3-pinanone to vinyl phosphorus compound. (R)-(-)-Phosphinothricin, an enantiomeric isomer, can also be prepared from the same chiral glycine Schiff base by choosing suitable reaction temperature.

Phosphinic acid esters and process for preparing the same

Disclosed is a novel process for preparing [(3-amino-3-carboxy)-propyl-1]phosphinic acid derivatives, comprising reacting an alkylalkylphosphonyl halide with a vinylmagnesium halide to form a vinylphosphinic acid derivative, and reacting the vinylphosphinic acid derivative with a Shiff's base to form the aimed product. Also disclosed is a novel intermediate compound formed during the course of the above process, which compound has the general formula: STR1 (wherein R1, R2, R3, R4 and R5 are as defined in the specification).

A PRACTICAL SYNTHESIS OF (+/-)-PHOSPHINOTHRICINE

A practical synthesis of (+/-)-phosphinothricine from trimethyl phosphite is described.

Phospho-Cope Rearrangement of Sodium Allylvinylphosphinate

Sodium allylvinylphosphinate (1) rearranges thermally to sodium hydrogen pent-4-enephosphonate (3) in virtually quantitative yield.The reaction probably constitutes a phospho-Cope rearrangement and presumably proceeds by way of the monomeric metaphosphonate 2 as a reactive intermediate.The half-time for the reaction is 4.67 h in water at 193.6+/- 1.0 deg C and 6.03 h in ethanol.By contrast, ethyl allylvinylphosphinate reacts in ethanol to give a mixture of compounds; although some of the product expected for a phospho-Cope is present in the mixture, the rearrangement is slower than that of the anion by a factor of at least 16.The mechanistic implications of these facts are discussed.