7515-17-5

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 3-(4-Methoxyphenyl)propiolate is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs.
Used in Agrochemical Production:
In the agrochemical industry, Methyl 3-(4-Methoxyphenyl)propiolate is utilized as an intermediate in the production of various agrochemicals, potentially enhancing crop protection and yield.
Used in Organic Compounds Synthesis:
Methyl 3-(4-Methoxyphenyl)propiolate is also used as an intermediate in the synthesis of organic compounds, contributing to the advancement of organic chemistry and the creation of novel materials.
Used in Medicinal Chemistry and Drug Discovery:
Methyl 3-(4-Methoxyphenyl)propiolate is employed in medicinal chemistry and drug discovery due to its potential to be a key component in the development of new therapeutic agents.
Used in Anti-Inflammatory and Antioxidant Research:
Although further research is needed, Methyl 3-(4-Methoxyphenyl)propiolate has been studied for its potential anti-inflammatory and antioxidant properties, indicating possible use in the development of treatments for inflammation and oxidative stress-related conditions.

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 123466-30-8 [(4-methoxyphenyl)ethynyl](phenyl)iodonium tosylate 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 79-22-1 methyl chloroformate 
• 696-62-8 para-iodoanisole 
• 922-67-8 propynoic acid methyl ester 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 77-78-1 dimethyl sulfate 
• 91059-50-6 3-(4-Methoxyphenyl)-cyano-propiolsaeure-anhydrid 
• 124-38-9 carbon dioxide 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 74-88-4 methyl iodide 
• 768-60-5 4-methoxyphenylacetylen 

Downstream Products

• 115665-09-3 5-(4-Methoxy-phenyl)-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 79230-08-3 (Z)-3-(Benzimidoyl-amino)-3-(4-methoxy-phenyl)-acrylic acid methyl ester 
• 79229-97-3 N-benzyl-3-(p-methoxyphenyl)propynamide 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 
• 464184-10-9 methyl 1,4,5,6-tetramethyl-3-(4'-methoxyphenyl)-bicyclo[2.2.0]hexa-2,5-diene-2-carboxylate 
• 1342892-01-6 2,2-diethyl 4-methyl 3-(4-methoxyphenyl)-5-phenyl-1-tosyl-1H-pyrrole-2,2,4(5H)-tricarboxylate 
• 1346619-05-3 C₁₇H₁₉N₃O₂S 
• 112271-44-0 N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide 
• 109346-00-1 3-(4-methoxyphenyl)propiolamide 
• 1139719-79-1 (Z)-methyl 3-(3-acetylamino-2,4,6-trimethylphenyl)-3-(4-methoxyphenyl)acrylate 
• 1139719-60-0 (E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methoxyphenyl)acrylate 

Relevant academic research and scientific papers

Oxidation of aromatic compounds: XI. Oxidation of methyl 3-(4-methoxyphenyl)propynoate in the system CF3COOH-CH 2Cl2-PbO2

Oxidation of methyl 3-(4-methoxyphenyl)propynoate in the system CF 3COOH-CH2Cl2-PbO2 at 0-2°C within 2 h affords in a preparative yield of 55% a product of oxidative dimerization, dimethyl 2,3-bis(4-methoxyphenylcarbonyl)but-2-ene-1,4- dicarboxylate (II) whose double bond is in E-configuration according to X-ray diffraction data.

trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines

trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Organocatalytic trans Phosphinoboration of Internal Alkynes

We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.

Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids

A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-

Synthesis of 1-Amino-2 H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

An efficient tandem cycloisomerization-amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.

Trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides

A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and ste

Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling

A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.

Palladium-Catalyzed Hydroalkylation of Alkynes with Cyclopropanols: Access to γ,δ-Unsaturated Ketones

A palladium-catalyzed hydroalkylation of alkynes with cyclopropanols has been developed. This reaction provided a straightforward way to the synthesis of γ,δ-unsaturated ketones in moderate to good yields, exhibiting high atom economy and Z/E selectivity. Deuterated tri-substituted alkenes could also be expediently produced by using deuterium oxide as a co-solvent. (Figure presented.).