3195-24-2

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL DIALLYLMALONATE is used as a starting material for the enantioselective synthesis of carbocyclic nucleoside analogues, which are important in the development of antiviral and anticancer drugs. Its role in creating these analogues is crucial for advancing medical treatments.
Used in Chemical Synthesis:
In the field of chemical synthesis, DIETHYL DIALLYLMALONATE is utilized as a component in ring-closing metathesis reactions. Its ability to function with low catalyst loading makes it an efficient and cost-effective option for these processes.
Used in Catalyst Research:
DIETHYL DIALLYLMALONATE is also used in the study and development of new catalysts. The cationic nickel-catalyzed cycloisomerisation of DIETHYL DIALLYLMALONATE, with monodentate phosphoramidites and Wilke's azaphospholene as ligands, has been reported, indicating its importance in the advancement of catalyst technologies.

InChI:InChI=1/C13H20O4/c1-5-9-13(10-6-2,11(14)16-7-3)12(15)17-8-4/h5-6H,1-2,7-10H2,3-4H3

Upstream product

• 556-56-9 allyl iodid 
• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 106-95-6 allyl bromide 
• 69161-61-1 2-(prop-2-en-1-yloxy)oxane 
• 996-82-7 sodium diethylmalonate 
• 29443-23-0 N,N,N-triethylprop-2-en-1-aminium bromide 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 591-87-7 Allyl acetate 
• 603-35-0 triphenylphosphine 
• 1823-91-2 1-phenylethyl cyanide 
• 557-31-3 3-ethoxyprop-1-ene 
• 3066-75-9 allyl diethyl phosphate 
• 35466-83-2 allyl methyl carbonate 

Downstream Products

• 66843-15-0 1,5,5-triallyl-barbituric acid 
• 780-59-6 5,5-diallyl-1-methyl-pyrimidine-2,4,6-trione 
• 3048-76-8 3,8-dimethyl-2.7-dioxaspiro<4.4>nonane-1,6-dione 
• 31930-24-2 3,3-diallyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 
• 52-43-7 5,5-diallylbarbituric acid 
• 18325-74-1 4-ethoxycarbonyl-1,6-heptadiene 
• 75456-45-0 2,7-dioxa-4,8-bis<(phenylseleno)methyl>spiro<4.4>nona-1,6-dione 
• 75456-44-9 4,4-bis(ethoxycarbonyl)-2,6-bis<(phenylseleno)methyl>oxane 
• 77414-08-5 3,3-Diallyl-7-chloro-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 
• 335-65-9 hydroperfluorooctane 
• 355-37-3 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane 
• 74-85-1 ethene 
• 21622-00-4 Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester 
• 60012-87-5 3,8-bis-bromomethyl-2,7-dioxa-spiro[4.4]nonane-1,6-dione 

Relevant academic research and scientific papers

Ring-closing olefin metathesis in the aqueous phase of amphiphilic conetworks consisting of fluorophilic and hydrophilic compartments

A Grubbs-Hoveyda-Type metathesis catalyst bearing a tris(perfluoroalkyl)silyl tag was immobilized in the fluorophilic phase of amphiphilic conetworks (APCNs). This catalytic system was applied to ring-closing metathesis (RCM) reactions in aqueous media. Different substrates were evaluated and with 10 mol% of catalyst at 60 °C good conversions were observed. Reuse of the catalytic system was possible, but resulted generally in lower conversions.

Reactions of 2-(perfluoroalkyl)ethane thiols with 1,6-heptadiene and 4-substituted 1,6-heptadienes: The synthesis of RFethanethio- cyclopentanoic and -dioic acids; and, "geminal-twin-tail" bis-(perfluoroalkylethanethio)alkanoic acids

Kinetic analysis of the free radical addition of n-C6F 13I to 1,6-heptadiene gives a rate ratio of cyclization to addition (kd1/kc) of 0.568 at 70°C; thus, the rate of cyclization (kc) is twice that of iodine transfer (kd1). By contrast, for n-C6F13CH2CH2SH (kd1/kc) = 14.4 at 70°C, and radical transfer of H from the thiol is 14.4 times the faster than cyclization. Substitution at the center of 1,6-heptadiene has a profound effect on the linear/cyclic adduct ratio. For the addition of n-C3F7I (RFI:diene= 2:0) the adduct ratios dramatically decrease in the order: 1,6-heptadiene (1.17) > 4-carboxy-1,6-heptadiene (0.0613) > 4,4-bis-ethoxycarbonyl-1,6- heptadiene (F(CH 2)3]2CHCO2R, or [R F(CH2)3]2C(CO2R) 2 must be synthesized by other means. For the reaction of R FCH2CH2SH with the dienes (1:1), the respective adduct ratios are 11.3 (n-C6F13), 0.370 (n-C 8F17), and 0.0716 (n-C6F13). However, adding the 4-carboxy-1,6-heptadiene slowly to four mols of n-C 8F17CH2CH2SH yields 98% of the geminal bis-adduct [RFCH2CH2S(CH 2)3]2CHCO2H, which is a new, fluorophilic, geminal-twin-tail acid.

REACTIONS OF ORGANOCOBALT COMPLEXES WITH BROMOESTERS: REGIOSPECIFIC SYNTHESIS OF ALLYL- AND CYCLOPROPYLMETHYL-SUBSTITUTED MALONIC AND ACETOACETIC ESTERS

Allyl(pyridine)cobaloximes RCo(dmgH)2Py (R = allyl) react readily with diethyldibromomalonate, diethylbromomethylmalonate and ethyl 2-bromoacetoacetate to give the corresponding allyl-substituted esters.Transfer of the allyl group occurs with complete rearrangement in all but one cases.Buten-3-yl(pyridine)cobaloximes react with diethylbromomalonate giving cyclopropylmethylmalonic esters.

Simple synthesis and anti-HIV activity of novel cyclopentene phosphonate nucleosides

A very simple synthetic route for novel cyclopentene phosphonate nucleosides is described. The characteristic cyclopentene moiety 6 was constructed via a ring-closing metathesis of divinyl 5 , which could be readily prepared from diethylmalonate. The condensation of the mesylate 11 with nucleobases (A,C,T,U) under nucleophilic substitution conditions (K 2CO3, 18-Crown-6, DMF) afforded the target nucleosides 12 , 13 , 14 , and 15 . In addition, the antiviral evaluations against various viruses were performed. Copyright Taylor & Francis Group, LLC.

Ruthenium-catalyzed cross-metathesis between diallylsilanes and electron-deficient olefins

Diallysilanes can be selectively coupled with electron-deficient olefins under cross-metathesis (CM) conditions using the Hoveyda-Grubbs catalyst to produce mono- and/or bis-CM compounds in good yield. The formation of the mono- and the bis-CM compounds depends on the nature of the electron-deficient olefin.

Generation of four five-membered rings in a one pot process. Studies directed toward the synthesis of dicyclopenta[a,d]pentalene via the tandem Pauson-Khand reaction

The synthesis of the four five-membered rings of a suitably functionalized parent system 15 of dicyclopenta[a,d]pentalene 2 has been accomplished via a tandem Pauson-Khand reaction in a one pot process.

Synthesis and anti-HCMV activity of novel 5′-norcarboacyclic nucleosides

A very simple route for synthesizing a novel carboacyclic version of 5￠-noraristeromycin is described. Condensation of the mesylates 9 and 23 with the natural nucleosidic bases (A, U, T, C) under standard nucleophilic substitution (K2CO3, 18-Crown-6, DMF) and deblocking conditions, afforded the target nucleosides 14, 15, 16, 17, 28, 29, 30, and 31. In addition, these compounds were evaluated for their antiviral properties against various viruses.

Metal-free Photochemical Atom Transfer Radical Addition (ATRA) of BrCCl3 to Alkenes

A simple, photochemical, and metal-free protocol for the atom transfer radical addition (ATRA) of bromotrichloromethane onto various alkenes is described. Among a range of organic molecules, phenylglyoxylic acid proved to be the most suitable photoinitiator to promote a sustainable process for the addition of bromotrichloromethane to olefins. This photochemical atom transfer radical protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields.

Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles

O,ω-Unsaturated N-tosyl alkoxyamines undergo unexpected RhIII-catalyzed intramolecular cyclization by oxyamination to produce oxygen-containing heterocycles. Mechanistic studies show that an aziridine intermediate seems to be responsible for the formation of the heterocycles, possibly via a RhV species.

Correction: Exploiting and understanding the selectivity of Ru-N-heterocyclic carbene metathesis catalysts for the ethenolysis of cyclic olefins to α,ω-Dienes (Journal of the American Chemical Society (2017) 139:37 (13117-13125) DOI: 10.1021/jacs.7b06947)

The isotropic chemical shielding (iso) was mislabeled as the isotropic chemical shift (iso) in Table S40, Figures 2, 4, S153 and in the respective discussion of these figures in the text. The corrected figures are shown below; the SI graphics are provided in the corrected SI file. In the conclusion section, "cyclic olefins" was incorrectly written as "cyclic dienes" to be the essential structural feature for the selective ethenolysis toward w-dienes. The ROMP activity of Ru-20 is not detectable in the "presence of ethylene"; this was incorrectly written as the "absence of ethylene". Equations 5 and 7, pages S47 and S135 respectively, had errors that have been fixed in the corrected SI file. None of the above affects any conclusions of the article. (Figure Presented).