1067-73-8

Usage

Uses

Used in the Synthesis of Organic Compounds:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a reactant for the synthesis of various organic compounds, including:
1. Oxa(bicyclo)octanone for use in preparing cycloheptane annulated furans:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a key intermediate in the synthesis of oxa(bicyclo)octanone, which is further utilized in the preparation of cycloheptane annulated furans. These furans have potential applications in the pharmaceutical and chemical industries.
2. Anatoxin-a and homoanatoxin via the Wittig reaction:
This phosphonate compound is employed in the Wittig reaction to synthesize anatoxin-a and homoanatoxin, which are biologically active alkaloids with potential applications in research and drug development.
3. α-Methylene-β-amino ketones:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a starting material in the synthesis of α-methylene-β-amino ketones, which are valuable building blocks in organic chemistry and have potential applications in the synthesis of pharmaceuticals and agrochemicals.
4. 2-Amino-5-phosphonoand 2-amino-4-(phosphonomethyl)thiophenes using the Gewald reaction:
This phosphonate compound is utilized in the Gewald reaction to produce 2-amino-5-phosphonoand 2-amino-4-(phosphonomethyl)thiophenes. These compounds have potential applications in the development of new materials and pharmaceuticals.
5. Aliphatic musk odorants:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a precursor in the synthesis of aliphatic musk odorants, which are widely used in the fragrance and perfume industry.
6. Oxoalkylphosphonates:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is also used in the synthesis of oxoalkylphosphonates, which have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H17O4P/c1-4-8(9)7-13(10,11-5-2)12-6-3/h4-7H2,1-3H3

Upstream product

• 816-40-0 1-Bromo-2-butanone 
• 122-52-1 triethyl phosphite 
• 3095-06-5 diethyl 2-butynylphosphonate 
• 141-52-6 sodium ethanolate 
• 683-08-9 Diethyl methylphosphonate 
• 79-03-8 propionyl chloride 
• 3095-05-4 diethyl 1,2-butadienylphosphonate 
• 589-57-1 diethyl phosphorylchloridite 
• 78-93-3 butanone 
• 74-96-4 ethyl bromide 
• 34170-81-5 diethyl (2-chloro-2-oxoethyl)phosphonate 
• 34170-83-7 (chloro-chlorocarbonyl-methyl)-phosphonic acid diethyl ester 
• 557-18-6 diethylmagnesium 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 139740-83-3 (3-Methyl-2,4-dioxo-4-phenyl-butyl)-phosphonic acid diethyl ester 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 109632-31-7 2-oxo-1-phenylbutylphosphonate de diethyle 

Relevant academic research and scientific papers

Reaction of Diethyl Phosphorochloridite with Enolates: A General Method for Synthesis of β-Keto Phosphonates and α-Phosphono Esters through C-P Bond Formation

The reaction of ketone enolates with diethyl phosphorochloridite, followed by air oxidation of the intermediate reaction products, has proven to be a general and convenient method for preparation of β-keto phosphonates.Fourteen β-keto phosphonates have been prepared by this method, in an average yield greater than 60percent.This procedure also appears to be applicable to preparation of both α-phosphono aldehydes and α-phosphono esters.Although special precautions may be necessary to avoid aldol condensation during formation of aldehyde enolates, in two cases it was shown that the resulting enolates react readily with diethyl chlorophosphite.Finally, a set of five ethyl esters was converted to α-phosphono esters by this method.Yields of the α-phosphono esters are influenced by steric hindrance at the enolate carbon, but the average yield for this series was ca. 70percent.Because this synthetic method relies upon an electrophilic phosphorus reagent for formation of the C-P bond, it is complementary to the traditional Arbuzov synthesis.On the basis of the 21 examples presented here, it appears to be more widely applicable.

A new synthesis of 2-aryl-2-oxoalkylphosphonates from triethyl phosphonoacetate

Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates.

Synthesis of the Aminocyclitol Core of Jogyamycin via an Enantioselective Pd-Catalyzed Trimethylenemethane (TMM) Cycloaddition

The use of β-nitroenamines as a new class of acceptors in the enantioselective Pd-catalyzed trimethylenemethane cycloaddition afforded differentiated 1,2-dinitrogen bearing cyclopentanes with three contiguous stereocenters. The utility of these acceptors was demonstrated with the efficient construction of the core of jogyamycin and aminocyclopentitols. Further elaboration of the cycloadducts provided a concise synthetic approach toward joygamycin.

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.

Addition of secondary amines to alkynephosphonates

Addition of secondary amines to diethyl alkynephosphonates, catalyzed by Cu(I) salts, proceeds regio- and stereospecifically and yields diethyl (E)-2-diethylaminooalkenephosphonates. The E configuration was established by analysis of the vicinal coupling constants between the phosphorus and carbon nuclei in the 13C NMR spectra of the reaction products and model compounds: 3JPC is 6-10 Hz at the cis arrangement of the coupled nuclei and 16 Hz or higher at the trans arrangement. In all the diethyl diethylaminoalkenephosphonates obtained, 3JPC is about 5 Hz, suggesting cis addition.

Addition of secondary amines to alkynylphosphonates

Addition of secondary amines to alkynylphosphonates catalyzed by Cu(I) salts proceeds regio- and stereospecifically to form (E)-2-(dialkylamino)alkenylphosphonates. The E-configuration was proved by analysis of 13C-31P vicinal spin-spin coupling constants in the NMR spectra of the products and authentic model compounds. The 3JPC constants in the model compounds fall in the range of 6-12 Hz for the cis arrangement of the coupled nuclei and are equal to or higher than 16 Hz for the trans configuration. Related coupling constants in the addition products are around 5 Hz, that is, corresponding to cis coupling.

Acylation of diethyl phosphonoacetic acid via the MgCl2/Et3N system: A practical synthesis of β-keto phosphonates

A one pot simple procedure for the synthesis of β-keto phosphonates has been developed using the MgCl2/Et3N base system to generate the magnesium enolate of diethyl phosphonoacetic acid. This intermediate reacts with acid chlorides or imidazolides to give, after workup, the title compounds in good yields.

Novel 1-phosphonyl radicals derived from 1-mono and 1,1-di-heterosubstituted 2-oxoalkylphosphonates as useful phosphotoorganic intermediates in organic synthesis

Novel 1-phosphonyl radicals 17 were obtained from 1-mono(Y=H X=Cl, Br, SMe) and 1.1-di (Y=X=Cl) hetero substituted 2-oxoalkylphosphonates 16 under the reductive conditions (n-Bu3SnH/AIBN) and utilized in the reactions with alkenes for the free-radical synthesis of highly functionalized phosphonates 19 and 20. The utility of the new approach has been demonstrated by the synthesis of methylenomycin B 13, a cyclopentanoid antibiotic, using the phosphonate 19d as well as by the synthesis of 4-diethoxyphosphoryl-2,3-dihydrofuran 22 and 2-diethoxyphosphoryloxy-heptan-5-one 23.

A new, effective approach for the C-C bond formation utilizing 1-, 2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and n-Bu3SnH/Et3B/O2 system

A new, practical synthesis of highly substituted phosphonates utilizing 1-, 2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and a catalytic or stoichiometric amounts of the n-Bu3SnH/Et3B/O2 reagent is described.

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.