40601-43-2

Upstream product

• 66130-90-3 diethyl <<(trimethylsilyl)oxy>carbonyl>methanephosphonate 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 10419-77-9 diethyl iodomethanephosphonate 
• 15972-15-3 1-cyclohexyl-butane-1,3-dione 
• 762-04-9 phosphonic acid diethyl ester 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 3095-95-2 diethylphosphonoacetic acid 
• 683-08-9 Diethyl methylphosphonate 
• 95-54-5 1,2-diamino-benzene 
• 30238-20-1 diethyl cyclohexylethynylphosphonate 

Downstream Products

• 1421338-23-9 C₂₂H₂₃N₃O₃S 

Relevant academic research and scientific papers

Silver-Catalyzed Oxidative C(sp3)?P Bond Formation through C?C and P?H Bond Cleavage

The silver-catalyzed oxidative C(sp3)?H/P?H cross-coupling of 1,3-dicarbonyl compounds with H-phosphonates, followed by a chemo- and regioselective C(sp3)?C(CO) bond-cleavage step, provided heavily functionalized β-ketophosphonates. This novel method based on a readily available reaction system exhibits wide scope, high functional-group tolerance, and exclusive selectivity.

Synthesis of β-ketophosphonates via AgNO3-catalyzed hydration of alkynylphosphonates: A rate-enhancement effect of methanol

β-Ketophosphonates were prepared via AgNO3-catalyzed hydration of alkynylphosphonates with a dramatic rate-enhancement effect of methanol. This benign aqueous-methanol method catalyzed by a low-cost catalyst has simple, atom-economical procedure, and was used effectively with a wide range of substrates.

Gold(I)-catalyzed hydration of alkynylphosphonates: Efficient access to β-ketophosphonates

A general, efficient, and highly regioselective protocol with the use of a gold(I) complex catalytic system for the transformation of alkynylphosphonates into the corresponding β-ketophosphonates has been successfully developed. This method produces a variety of β-ketophosphonates with the advantages of mild reaction conditions, high functional-group tolerance, and excellent yields. An efficient and mild gold-catalyzed hydration process for the regioselective synthesis of β-ketophosphonates directly from alkynylphosphonates is described. Twenty-two examples with yields of 85-97 % are reported. Different substituents including substituted aryl, alkyl, chloro, ester, sulfonoxyl, and phthalimide groups are tolerated; XPhos = 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, Tf = trifluoromethylsulfonyl. Copyright

SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: A highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate

In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford β-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate.

Novel cobalt(0)- or magnesium-mediated approaches to β-ketophosphonates

Two novel approaches to β-ketophosphonates, based on cobalt(0)- or magnesium-mediated reactions of α-halophosphonates with esters are described.

One pot synthesis of mono- and spirocyclic α-phosphonato-α,β- unsaturated cycloenones

A one pot ozonolysis/intramolecular aldol condensation(with the aid of T(s)OH and Et3N as catalysts) of β-keto-ω-alkenylphosphonates provided the α-phosphonato-α,β-unsaturated cycloenone with good yields.

Acylation of in situ generated trimethylsilyl diethylphosphonoacetate using magnesium chloride-triethylamine: a practical synthesis of β-keto phosphonates

In situ generated trimethylsilyl diethylphosphonoacetate from diethyl phosphonoacetic acid can be acylated with carboxylic acid chlorides in the presence of magnesium chloride to prepare a variety of β-keto phosphonates.This synthetic methods is suitable for the preparation of β-keto phosphonates in the laboratory and also for large-scale production.

SYNTHESE D'HETEROCYCLES α-PHOSPHONIQUES. NOUVEAUX DEVELOPPEMENTS

Synthesis of α-phosphonic heterocycles is described by condensation of 1,2- 1,3- or 1,4-bisnucleophiles with β-phosphonic enamines 2 bearing a functional group.From guanidine and analogs 4-diethoxyphosphinyl pyrimidines 5 and 8 are obtained with yields up to 50percent .Substituted hydrazines give 4-diethoxyphosphinyl pyrazoles 11 with very good yields.With hydroxylamine a spontaneous dehydration gives the enolic form 18 of a β-ketophosphonate α-nitrile.Orthophenylene diamine is a special example in fact the departure β-ketophosphonate is recovered with benzimidazole elimination.

PREPARATION QUASI QUANTITATIVE DE PHOSPHONATES β-CARBONYLES PAR L'EMPLOI D'UNE BASE RELAIS, LE DIPAL

Preparation of oxo-2 alkylphosphonates by anionic route is a process of limited scope.The low yields often encountered in the initial phosphonylation step are certainly due to regeneration of the departure phosphonate through acid-base exchanges.This drawback can be overcome by proper choice of the metalating agent.The use of LDA makes the procedure efficient and most stoechiometric, and it lends itself to the preparation of a wide range of β-ketophosphonates free of by-products.

PHOSPHOR- UND SCHWEFELSUBSTITUIERTE ALLENE IN DER SYNTHESE I : EINFACHE SYNTHESE VON β-KETOPHOSPHONATEN AUS 1-ALKIN-3-OLEN

Allenic phosphonates, readily accessible from 1-alkin-3-ols, the addition products of 1-alkines to aldehydes or ketones, can be transformed to β-ketophosphonates by nucleophilic addition of diethylamine and subsequent hydrolysis of the formed enamines.