15378-09-3

Usage

Uses

Used in Pharmaceutical Synthesis:
DIMETHYL 2-(4-METHOXYBENZYL)MALONATE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Agrochemical Synthesis:
In the agrochemical industry, DIMETHYL 2-(4-METHOXYBENZYL)MALONATE is used as a precursor for the development of new pesticides and herbicides. Its versatile nature enables the creation of novel agrochemicals with enhanced performance and selectivity.
Used in Organic Synthesis:
As a building block in organic synthesis, DIMETHYL 2-(4-METHOXYBENZYL)MALONATE is used for constructing complex molecular structures. Its reactivity and aromatic benzyl group make it a valuable component in the synthesis of various organic compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, DIMETHYL 2-(4-METHOXYBENZYL)MALONATE is used as a reagent for the development of biologically active compounds. Its ability to serve as a precursor for a variety of compounds makes it an essential tool in drug discovery and development processes.

InChI:InChI=1/C13H16O5/c1-16-10-6-4-9(5-7-10)8-11(12(14)17-2)13(15)18-3/h4-7,11H,8H2,1-3H3

Upstream product

• 18424-76-5 sodiodimethylmalonate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 7443-25-6 dimethyl 2-(4-methoxybenzylidene)malonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 2746-25-0 p-Methoxybenzyl bromide 
• 6773-29-1 dimethyl diazomalonate 

Downstream Products

• 132629-16-4 dimethyl 2-(4-methoxybenzyl-2-(¹¹C)methyl)malonate 
• 405064-32-6 C₁₁H₁₀Cl₂O₃ 

Relevant academic research and scientific papers

Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis

A cooperative Lewis acid/photocatalytic reduction of salicylaldehyde-derived arylidene malonates provides access to a versatile, stabilized radical anion enolate. Using these unusual umpolung operators, we have developed a novel route to access densely fu

Reaction of tricarbonyl[(1-4-η)-2-methoxy-5-vinylidene-cyclohexa-1,3- diene]iron derivatives with carbene: (2+1) Cycloaddition for the rapid synthesis of spiro[2,5]octane

Tricarbonyl[(1-4-η)-2-methoxy-5-methylene-cyclohexa-1,3-diene]iron (1a) and tricarbonyl[(1-4-η)-2-methoxy-5-isopropylene-cyclohexa-1,3-diene]iron (1b) complexes are unstable 4-vinylidene cyclohexanone equivalents and these react regio- and stereoselectively with carbenes and metallocarbenes to give spiro[2,5]octane ring system. The (2+1) cycloaddition reaction provides a rapid entry into spiro[2,5]octane ring system. In cases where the carbene and metallocarbene contain a good bulky leaving group or an electron-withdrawing group, the cyclopropane ring-opening products are obtained.

Gallium-assisted transfer hydrogenation of alkenes

We report a rare case of alkene transfer hydrogenation using a main-group compound instead of a transition-metal complex as catalyst. We disclosed that 1, 4-cyclo-hexadiene can be used as H2 surrogate towards olefin reduction in the presence of [IPrGaCl2][SbF6]. Hydrogenative cycli-zations have also been carried out because this cationic gallium complex is also a potent hydroarylation catalyst.

Photoredox/Nickel Dual Catalysis Enables the Synthesis of Alkyl Cyclopropanes via C(sp3)-C(sp3) Cross Electrophile Coupling of Unactivated Alkyl Electrophiles

A facile synthesis of mono-, 1,1- and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis is demonstrated. The challenging intramolecular C(sp3)-C(sp3) cross-electrophile coupling of readily available unactivated 1,3-dialkyl electrophiles was performed under mild conditions that allowed traditionally reactive functional groups to be included. Mechanistic inspection and control experiments revealed the importance of dual catalysis and that the reaction proceeds via a stepwise oxidative addition followed by an intramolecular SN2 reaction.

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Catalytic Use of Low-Valent Cationic Gallium(I) Complexes as π-Acids

Transformations of alkene and alkyne substrates relevant to π-Lewis acid catalysis have been performed using low-valent Ga(I) species for the first time. [Ga(I)(PhF)2]+[Al(ORF)4]? and gallium dichloride (i. e. [Ga(I)]+[GaCl4]?) proved to be efficient catalysts for cycloisomerizations, Friedel-Crafts reactions, transfer hydrogenations, and reductive hydroarylations. Their activity is compared to more common Ga(III) complexes. This study shows that even the readily available and yet overlooked gallium dichloride salt can be a more active π-Lewis acid catalyst than gallium trichloride or other Ga(III) species. (Figure presented.).

Palladium catalyzed direct benzylation/allylation of malonates with alcohols-: In situ C-O bond activation

High step- and atom-economy are the endlessly pursued in organic and pharmaceutical syntheses. Herein, a new method for directly coupling benzyl/allyl alcohols with malonates via a palladium catalyzed Tsuji-Trost type reaction was developed. The reaction was carried out in an organic carbonate solvent which would activate alcohols in situ, replacing the traditional pre-synthesized carbonates. The new process demonstrated high efficiency, high selectivity and high generality. A wide variety of mono-substituted and bis-substituted malonates were selectively produced under different conditions, and this method represents a more step- and atom-economical and environmentally benign synthetic protocol.

Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst

A one-pot two-step reaction (Knoevenagel condensation - reduction of the double bond) has been developed using calcium hydride as a reductant in the presence of a supported noble metal catalyst. The reaction between carbonyl compounds and active methylene

A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids

α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.

A Facile one-pot benzylation of sodium enolates using trifluoromethanesulfonic anhydride and diphenyl sulfoxide

A facile one-pot C-benzylation of various sodium enolates derived from methyl malonate, β-ketoesters, a β-cyanoester, a β-cyanosulfone, ketones and a carboxylic ester is reported. Reaction of alkoxydiphenylsulfonium salts formed by treating various benzyl alcohols with diphenyl sulfide bis(trifluoromethanesulfonate) (derived from trifluoromethanesulfonic anhydride and diphenyl sulfoxide) proceeded smoothly, and the corresponding C-benzylated products were afforded in good to high yields.