27174-71-6

Usage

Uses

Used in Fragrance and Flavor Industry:
Methyl 2-(1-adamantyl)acetate is used as a flavoring agent for its pleasant taste, enhancing the sensory experience of food products. Its aromatic properties also make it a popular ingredient in perfumes and other scented products, where it contributes to creating appealing and complex fragrances.
Used in Pharmaceutical Applications:
Methyl 2-(1-adamantyl)acetate is studied for its potential anti-inflammatory and anti-cancer properties. This research indicates that it may have therapeutic applications, particularly in the development of treatments for inflammatory conditions and various types of cancer.

InChI:InChI=1/C13H20O2/c1-15-12(14)8-13-5-9-2-10(6-13)4-11(3-9)7-13/h9-11H,2-8H2,1H3

Upstream product

• 67-56-1 methanol 
• 32132-59-5 2-((1R,3R,5R,7R)-adamantan-2-yl)acetyl chloride 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 186581-53-3 diazomethane 
• 917-64-6 methyl magnesium iodide 
• 19835-38-2 1-adamantylacetyl chloride 
• 101706-12-1 methyl bromo(3-bromo-1-adamantyl)acetate 
• 110-89-4 piperidine 
• 173167-08-3 O-methyl (1-adamantyl)thioacetate 

Downstream Products

• 4942-47-6 (adamant-1-yl)-acetic acid 
• 6240-11-5 2-(adamant-1-yl)ethanol 

Relevant academic research and scientific papers

Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters

Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.

Preparative synthesis of vinyl diamondoids

We describe a convenient four-step preparation of 1-vinyl adamantane, 1-vinyl diamantane, and 4,9-divinyl diamantane from the respective diamondoid acetic acids in 50-80% isolated yields involving esterification, reduction, and hydrobromination/dehydrobromination. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: Further refinement of tentative pharmacophore group

Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well.

Adamantyl-Containing O-Monothioesters. II. Synthesis and Chemical Transformations of O-Methyl (1-Adamantyl)thioacetate in Reaction with Piperidine

O-Methyl (1-adamantyl)thioacetate has been prepared for the first time by reaction of methyl (1-adamantyl)acetate with phosphorus pentasulfide in dioxane.The reaction of this product with piperidine yields corresponding S-ester, (1-adamantyl)aceto- and (1-adamantyl)thioacetopiperidides, and N-methylpiperidine.A mechanism of this reaction has been proposed, based on comparative analysis of behavior of O-methyl 1-adamantylthioacetate and its analogs, adamantane-1-thiocarboxylic and thiopivalic acid O-esters.

SYNTHESIS OF ASYMETRIC DERIVATIVES OF 3,7-DIMETHYLENEBICYCLONONANE

The fragmentation of asymmetric dibromo derivatives of adamantane was studied in order to synthesized asymmetric 3,7-dimethylenebicyclononanes.A zinc-copper couple was used as reagent for the fragmentation.During the fragmentation of methyl bromo(3

Oxy-Functionalization of Adamante-1-acetic Acid and Adamantane-1-carboxylic Acid by the Ferrous Iron-Molecular Oxygen System in Aqueous Solution

Oxygenation reactions of adamantanes with ferrous iron-molecular oxygen in phosphate buffer were investigated and the structures of the products were elucidated.In the reaction of adamantane-1-acetic acid (1a), five oxygenated products, the C(2)-oxo, C(4)-oxo, C(2),C(6)-dioxo, C(4)-ol, and C(3)-ol derivatives, were obtained.Similar oxygenation also occurred in the reaction of adamantane-1-carboxylic acid (2a) to give three products, the C(4)-oxo, C(4)-ol, and C(3)-ol derivatives.The oxy-functionalization of 1a and 2a in 0.5M phosphate buffer (pH 6.8) was found to occur almost quantitatively on addition of an appropriate amount of ferrous iron.

Synthesis of 1-adamantyl and 1-adamantylmethyl alkyl ketones

The reaction of 1-adamantanecarboxylic and 1-adamantylacetic acids with Grignard reagents in the presence of cuprous chloride or iodide gave the corresponding ketones.