83026-51-1

Usage

Type of compound

propionic acid derivative

Phenyl ring substituents

two methoxy groups at positions 2 and 5

Therapeutic potential

anti-inflammatory and analgesic properties

Central nervous system interactions

being investigated for its potential as a treatment for neurological disorders

Drug development

may have potential as a drug candidate for the development of new pharmaceutical products

Upstream product

• 83026-47-5 diethyl α-<1-(2,5-dimethoxyphenyl)>-α-methylmalonate 
• 150-78-7 1,4-dimethoxybezene 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 124-38-9 carbon dioxide 
• 14568-68-4 1,4-dimethoxy-2-vinylbenzene 
• 83026-34-0 diethyl acetoxy(2,5-dimethoxyphenyl)propanedioate 
• 83026-20-4 diethyl (2,5-dimethoxyphenyl)tartronate 

Downstream Products

• 1239016-37-5 (R)-2-(2,4-dimethoxyphenyl)propanoic acid 
• 1239016-25-1 di(1-naphthyl)methyl (S)-2-(2,5-dimethoxyphenyl)propanoate 

Relevant academic research and scientific papers

Cp2TiCl2-Catalyzed Regioselective Hydrocarboxylation of Alkenes with CO2

Cp2TiCl2-catalyzed regioselective hydrocarboxylation of alkenes with CO2 to give carboxylic acids in high yields has been developed in the presence of iPrMgCl. The reaction proceeds with a wide range of alkenes under mild conditions. Styrene and its derivatives can transform to α-aryl carboxylic acids, and aliphatic alkenes can transform to form alkanoic acids.

Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2

The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO 2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2).

Ester Enolates from α-Acetoxy Esters. Synthesis of Aryl Malonic and α-Aryl Alkanoic Esters from Aryl Nucleophiles and α-Keto Esters

Ester enolates are generated by reductive α-deacetoxylation of α-acetoxy-α-arylmalonic esters or α-acetoxy-α-arylalkanoic esters with lithium in liquid ammonia or sodium α-(dimethylamino)naphthalenide in hexamethylphosphoramide-benzene.Since the requisite α-acetoxy esters are available from aryl nucleophiles, the reductions provide effective new synthetic routes to arylmalonic esters and α-arylalkanoic esters.For example, 2-(p-isobutylphenyl)propionic acid (ibuprofen, a commercially important nonsteroidal antiinflammatory agent) is obtained in 73percent yield overall from isobutylbenzene.Arenes, aryllithiums, or arylmagnesium halides react with α-keto esters, e.g., diethyl oxomalonate, ethyl pyruvate, methyl phenylglyoxalate, or alkyl glyoxylates, to afford α-hydroxy esters.These are acetylated with acetic anhydride-triethylamine and p-(dimethylamino)pyridine as a catalyst.Reductive α-deoxygenation then allows replacement of the acetoxy group by hydrogen or an alkyl group.