179248-90-9

Usage

Uses

Used in the Food and Beverage Industry:
1-(4-methylphenyl)prop-2-ynyl acetate is used as a flavoring agent for its sweet, fruity odor, enhancing the taste and aroma of various products in the food and beverage industry.
Used in the Perfume and Scented Products Industry:
1-(4-methylphenyl)prop-2-ynyl acetate is used as a fragrance ingredient in the production of perfumes and other scented products, contributing to their pleasant and attractive scents.
Used in Medical and Pharmaceutical Applications:
1-(4-methylphenyl)prop-2-ynyl acetate is used in some medical and pharmaceutical applications due to its potential antimicrobial properties, offering benefits in the development of treatments and products for various health-related issues.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 106-38-7 para-bromotoluene 
• 132589-36-7 1-(4-methylphenyl)prop-2-yn-1-ol 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 4301-14-8 acetylenemagnesium bromide 
• 910219-57-7 1-(4-methylphenyl)-3-(trimethylsilyl)-2-propyn-1-ol 
• 75-36-5 acetyl chloride 

Downstream Products

• 1041175-17-0 N-methyl-N-[1-(4-methylphenyl)-2-propynyl]aniline 
• 1186338-41-9 C₁₃H₁₂F₂O₂ 
• 1526920-99-9 2-methyl-2-[1-(4-methylphenyl)prop-2-ynyl]cyclohexane-1,3-dione 
• 1519102-95-4 N-4-toluenesulfonyl-(E)-3-(4-methylphenyl)prop-2-enamide 

Relevant academic research and scientific papers

Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition

A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).

Convenient synthesis of allenylphosphoryl compounds: Via Cu-catalysed couplings of P(O)H compounds with propargyl acetates

A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.

Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives

A highly efficient cascade sequence for syntheses of 2,3-disubstituted imidazo[1,2-a]pyridines with exclusive regioselectivity in moderate to excellent yields has been developed. This cascade was initiated through propargylation of 2-aminopyridines at pyridine-nitrogen with propargyl alcohol derivatives using Cu(II)-Pybox as catalyst and followed by an intramolecular cyclization and isomerization. Besides 2-aminopyridine, less reactive 2-aminopyrimidine, 2-aminopyrazine and 3-aminopyridazine were also suitable in this cascade.

Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex

Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.

Stereocontrol in palladium-catalyzed propargylic substitutions: Kinetic resolution to give enantioenriched 1,5-enynes and propargyl acetates

Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily

Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)

The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.

Asymmetrie copper-catalyzed propargylic substitution reaction of propargylic acetates with enamines

Enamines served as carbon-nucleophiles for the first time In the Cu-catalyzed asymmetric propargylic substitution reaction of propargylic acetates, providing corresponding chiral β-ethynyl-substituted ketones In high yields and In good to high enantioselectivity.

Copper-catalyzed asymmetric propargylic substitution reactions of propargylic acetates with amines

(Chemical Equation Presented) Flexing your bipheps: Enantioselective propargylic substitution reactions of propargylic acetates with amines catalyzed by a copper-(R)-Cl-MeO-biphep or -binap complex give the corresponding propargylic amines in excellent yi

Aryl propargylic alcohols of high enantiomeric purity via lipase catalyzed resolutions

A variety of substituted aryl propargylic alcohols were prepared via lipase catalyzed resolutions, the enantioselective hydrolysis of the corresponding esters being the method of choice.