14360-50-0

Usage

Uses

Used in Food Industry:
2-HEXANOYLFURAN is used as a flavoring agent for its sweet, fruity, green, waxy, and beany taste characteristics. It enhances the overall taste and aroma of various food products, making it a popular choice in the food additives market.
Used in Fragrance Industry:
Due to its chemical similarity with pentyl-2-furyl ketone, which has an apricot and peach-like odor, 2-HEXANOYLFURAN can also be utilized in the fragrance industry. It can contribute to the creation of unique and appealing scents for various products, such as perfumes, cosmetics, and personal care items.
Used in Chemical Research:
2-HEXANOYLFURAN's unique chemical properties make it a valuable compound for research purposes. It can be used in the development of new chemical processes, synthesis of novel compounds, and exploration of its potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C10H14O2/c1-2-3-5-9(11)8-10-6-4-7-12-10/h4,6-7H,2-3,5,8H2,1H3

Upstream product

• 110-00-9 furan 
• 142-61-0 Hexanoyl chloride 
• 617-90-3 2-furancarbonitrile 
• 693-25-4 n-pentylmagnesium bromide 
• 142-62-1 hexanoic acid 
• 13331-23-2 fur-2-ylboronic acid 
• 2051-49-2 n-hexanoic anhydride 
• 70-18-8 GLUTATHIONE 
• 110-53-2 1-Bromopentane 
• 95091-92-2 N-methoxy-N-methyl-2-furancarboxamide 
• 885480-76-2 2-furyl-2-n-pentyl-1,3-dithiane 
• 98-01-1 furfural 
• 109-67-1 1-penten 

Relevant academic research and scientific papers

Hydroacylation of 1-alkene with heteroaromatic aldehyde by Rh(I) and additives

Hydroacylation of 1-alkene with a heteroaromatic aldehyde such as pyridinecarboxaldehyde, thiophenecarboxaldehyde and furfural derivatives under cocatalyst of Wilkinson's complex and 2-amino-3-picoline gave poor yield of hydroacylated product. The addition of a catalytic amount of bis(cyclopentadienyl)zirconium dichloride or bis(cyclopentadienyl)titanium dichloride as an additive dramatically increased the yield of the hydroacylated ketone product.

De Novo Asymmetric Synthesis of (+)-Monanchorin

A de novo asymmetric total synthesis of the guanidine alkaloid natural product (+)-monanchorin has been achieved in nine steps from the commodity chemicals furan and caproic acid. The asymmetry of the route was introduced by a Noyori reduction of an acylfuran. In addition, this route relies upon an Achmatowicz rearrangement, a diastereoselective palladium catalyzed glycosylation, reductive amination, and an acid catalyzed bicyclic guanidine mixed acetal formation.

Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes

To understand the effect of lipid degradation on Maillard formation of meaty flavors, initial reaction intermediates in model systems of glucose–glutathione with hexanal, (E)-2-heptenal, or (E,E)-2,4-decadienal were identified by HPLC–MS and by NMR. Besides Amadori compounds, hemiacetals and thiazolidines via addition of sulfhydryl to carbonyl or to the conjugated olefinic bond were found. Concentrations of all intermediates increased with reaction time while degradation of the intermediates with a glutathione moiety helped formation of thiazolidines with cysteinylglycine. The unsaturated aldehydes (E)-2-heptenal and (E,E)-2,4-decadienal exhibited high reactivity against glucose for glutathione, yielding higher levels of intermediate compounds than from glucose. Heating prepared intermediates reversibly released the original aldehydes, which caused various compounds formed by retro-aldol, oxidation, etc. to react with H2S and NH3. Among them, formation pathways including 3-nonen-2-one, 2-hexanoylfuran, and six dialkylthiophenes (e.g., 2-ethyl-5-(1-methylbutyl)thiophene) were proposed for the first time.

Method of making 2-furylalkylketones

A method of making a compound by: providing a furyl compound being 2-furoyl chloride or corresponding carboxylic acid, amide, ester, anhydride, or lactone; reacting the furyl compound with CH3O(CH3)NH.HCl to form an amide; reacting the amide with an alkane Grignard reagent or alkyllithium to form a chelated intermediate; and reacting the chelated intermediate with an aqueous acid to form a (2-furyl)-alkylketone.

Process for the preparation of 2-furyl-n-pentylketone and longer chain analogs

A process of making furfural-derived ketones is disclosed. These compounds may be useful as marine antifouling agents. The process uses the steps of: reacting a furfural with 1,3-dithiopropane to form a 1,3-dithiane derivative; metalizing the 1,3-dithiane derivative to form a metalodithiane derivative; reacting the metalodithiane derivative with a halide or pseudohalide to form a ketone precursor; and hydrolyzing the ketone precursor to form a furyl ketone.

Palladium-catalyzed synthesis of aryl ketones from boronic acids and carboxylic acids activated in situ by pivalic anhydride

A new palladium-catalyzed cross-coupling reaction between arylboronic acids and mixed anhydrides, generated in situ from carboxylic acids and pivalic anhydride, is presented. Optimization of the new catalyst and the reaction conditions led to the development of a convenient one-pot ketone synthesis directly from carboxylic and boronic acids in the presence of different (phosphane)palladium complexes in wet THF at 60 °C. Systematic studies were performed to elucidate the reaction mechanism of this transformation. The scope and the limitations of the new process are demonstrated by the synthesis of 33 functionalized ketones. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.