16115-01-8

Upstream product

• 36190-35-9 Dimethyl trimethylsilyloxybenzylphosphonate 
• 813-77-4 Dimethyl chlorophosphate 
• 18106-71-3 dimethyl benzoylphosphonate 
• 868-85-9 Dimethyl phosphite 
• 121-45-9 phosphorous acid trimethyl ester 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 70-11-1 α-bromoacetophenone 
• 6329-46-0 dimethyl 1-hydroxy-1-phenylmethylphosphonate 
• 32249-59-5 tetraester methylique de l'acide methane hydroxy-1 phenyl-1 diphosphonique-1,1' 
• 107-10-8 propylamine 

Relevant academic research and scientific papers

Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solvent ess conditions

The synthesis of hydroxy-methyl-enebisphosphonates (2a-c) by the addition of dialkyl phosphite to the carbonyl group of the corresponding α-oxophosphonate (1a-c) was studied under microwave irradiation (MW) and solventless conditions in the presence of di

Phenyl-, benzyl-, and unsymmetrical hydroxy-methylenebisphosphonates as dronic acid ester analogues from α-oxophosphonates by microwave-assisted syntheses

The microwave (MW)-assisted addition of dialkyl phosphites to α-oxophosphonates was investigated and optimized under solventless conditions to provide the phenyl- and benzyl-hydroxy-methylenebisphosphonates efficiently by suppressing the rearrangement sid

Darzens reaction of acyl phosphonates with α-bromo ketones: Selective synthesis of cis- and trans-epoxyphosphonates

(Chemical Equation Presented) Acyl phosphonates with α-halo ketones in the presence of bases at room temperature afford cis- and trans-epoxyphosphonates in good chemical yields and high selectivities using different bases. The diastereoselectivity of this reaction is easily controlled by changing the base. Changing the base from Cs2CO3 to DBU changed the diastereomeric ratio (transieis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete conversion to the corresponding cis isomer.

gem-Diphosphonate and gem-phosphonate-phosphate compounds with specific high density lipoprotein inducing activity

New diphosphonate compounds and related derivatives were synthesized and investigated for their activity in specifically inducing plasma high density lipoproteins (HDL) and high density lipoprotein cholesterol (HDL-C) in normal rats. The screening of nume

α CETOPHOSPHONATES ET ESTERS CYCLIQUES D'HYDROXYMETHYLENES DIPHOSPHONATES SYNTHESES, STRUCTURES ET HYDROLYSE

Synthesis of symmetrical diesters derived from hydroxy methylene diphosphonic acids 1 to 8 is described either in one step or via the corresponding α ketophosphonate 1a to 8a.Study of the diphosphonates (1 to 6) -> phosphate-phosphonates (1b to 6b) isomerization has been realized.Results related to peculiar cases in connection with nonsymmetrical esters 10, 11, 17 and study of the hydrolysis reaction of diphosphonates are presented.

THE REACTION OF PHOSPHITES WITH AROYLPHOSPHONATES IN THE PRESENCE OF PROTON DONORS-REVERSE NUCLEOPHILIC ADDITION TO CARBONYL GROUPS

Trimethyl phosphite attacks the carbonyl oxygen of aromatic α-ketophosphonates in the presence of proton donors such as carboxylic acids.The intermediate quasi-phosphonium salts (6) either demethylate to a diphosphorus compound (4) in the normal Arbusov manner or dealkylate to give a phosphonate (5) and trimethyl phosphate.

Acylphosphonates: P-C Bond Cleavage of Dialkyl Acylphosphonates by Means of Amines. Substituent and Solvent Effects for Acylation of Amines

Studies on the benzoylation of amines of dialkyl benzoylphosphonates (1A-F) were described in detail. Stoichiometric reactions of diethyl benzoylphosphonate (1B) with a variety of amines (2a-i) gave amides as the main products along with diethyl phosphonate (4B) and α-(phosphoryloxy)benzyl phosphonate (5B). The yields of amides increased with the ratio of 1B/2a-i. The use of hindered dialkyl benzoylphosphonates resulted in high yields of amides while the reaction rates decreased markedly. The benzoylations of n-propylamine (2d) with 1B in various solvents having dielectric constants of 1.9-36.7 were conducted. The yields of N-n-propylbenzamide (3d) and 5B were surprisingly almost constant. However, the reaction rates varied as follows. In nonpolar solvents such as n-hexane and cyclohexane benzoylation was remarkably rapid while the benzoylation in methylene chloride was much slower than that in other solvents used. Compound 1B underwent smooth reaction with aliphatic amines but did not react with aromatic amines under the same conditions. Selective N-benzoylation of the bifunctional amine, ethanolamine, was achieved by means of diisopropyl benzoylphosphonate (1C) in tetrahydrofuran. The use of the hindered dialkyl benzoylphosphonate 1C resulted in poorer yields of amides in the case of the reaction with a hindered amine such as diethylamine, but higher yields of amides in the case of primary amines. Addition of triethylamine and 4-(dimethylamino)pyridine (DMAP) slightly accelerated the benzoylation, but yields of amides were similar to those in the absence of the catalysts. Optimum conditions for high yields of amides were proposed for the practical use of dialkyl benzoylphosphonates as the acylating agents in the present reaction.