727401-23-2

Usage

Structure

Contains a cyclopentanone ring with a phenylethyl substituent and an acetyl group

Common uses

Flavor and fragrance ingredient

Aroma

Sweet, floral, fruity

Found in

Food, beverages, perfumes, personal care items

Value

Valuable ingredient for creating scents and flavors

Reactivity

Used in synthesis of other chemicals and pharmaceuticals

Upstream product

• 1670-46-8 2-acetylcyclopentanaone 
• 98-85-1 1-Phenylethanol 
• 100-42-5 styrene 

Downstream Products

• 1234702-35-2 butyl 5-acetyl-6-phenylheptanoate 

Relevant academic research and scientific papers

Graphene oxide catalyzed ketone α-alkylation with alkenes: Enhancement of graphene oxide activity by hydrogen bonding

Direct α-alkylation of carbonyl compounds represents a fundamental bond forming transformation in organic synthesis. We report the first ketone-alkylation using olefins and alcohols as simple alkylating agents catalyzed by graphene oxide. Extensive studies of the graphene surface suggest a pathway involving dual activation of both coupling partners. Notably, we show that polar functional groups have a stabilizing effect on the GO surface, which results in a net enhancement of the catalytic activity. The method represents the first alkylation of carbonyl compounds using graphenes, which opens the door for the development of an array of protocols for ketone functionalization employing common carbonyl building blocks and readily available graphenes.

Carbon-supported iron-ionic liquid: An efficient and recyclable catalyst for benzylation of 1,3-dicarbonyl compounds with alcohols

The effect of the addition of ILs with non-coordinating anions on the iron-catalyzed benzylation of 1,3-dicarbonyl compounds with alcohols under solvent free conditions has been evaluated. Among them, the presence of those containing the bistriflimide anion was found to be crucial for selectivity towards the benzylated product in a homogenous reaction. Therefore, the catalytic activity of Fe(OTf)3-N4111NTf2 combination supported on carbon materials with different textural and chemical surface properties has been studied. In the heterogeneous phase, reaction selectivity was also enhanced by the addition of the IL. However, substantial differences between the activities of different Fe-IL/carbon material catalytic systems were observed, indicating the influence of carbon support properties. With regards to selectivity, the best results were obtained using carbon supports with low microporosity. Moreover, the presence of oxygen functional groups on the carbon surface improved catalyst recycling. the Partner Organisations 2014.

Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Bronsted acids

(Chemical Equation Presented) We have developed an environmentally benign synthetic approach to nucleophilic substitution reactions of alcohols that minimizes or eliminates the formation of byproducts, resulting in a highly atom-efficient chemical process. Proton- and metal-exchanged montmorillonites (H- and Mn+-mont) were prepared easily by treating Na +-mont with an aqueous solution of hydrogen chloride or metal salt, respectively. The H-mont possessed outstanding catalytic activity for nucleophilic substitution reactions of a variety of alcohols with anilines, because the unique acidity of the H-mont catalyst effectively prevents the neutralization by the basic anilines. In addition, amides, indoles, 1,3-dicarbonyl compounds, and allylsilane act as nucleophiles for the H-mont-catalyzed substitutions of alcohols, which allowed efficient formation of various C-N and C-C bonds. The solid H-mont was reusable without any appreciable loss in its catalytic activity and selectivity. Especially, an Al3+-mont showed high catalytic activity for the α-benzylation of 1,3-dicarbonyl compounds with primary alcohols due to cooperative catalysis between a protonic acid site and a Lewis acidic Al3+ species in its interlayer spaces.

Bronsted acid-catalyzed benzylation of 1,3-dicarbonyl derivatives

The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Bronsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are carried out in air using undried solvents, with water being the only side product of the process.

A general and efficient iron-catalyzed benzylation of 1,3-dicarbonyl compounds

Various CH-acidic 1,3-dicarbonyl compounds and methyl 3-acetamidobut-2- enoate react with benzylic alcohols to give the corresponding 2-benzylated products in good to excellent yield. Typically, reactions proceed under mild conditions (50-80°C; air) in the presence of catalytic amounts of inexpensive iron chloride hexahydrate. The benzylation of 4-hydroxycoumarin gives the pharmaceutically interesting 4-hydroxy-3-(1-phenylethyl)-2H-chromen-2- ones. As an example the anticoagulant Phenprocoumon is prepared in one step from commercially available substrates in 94 % yield.

Bronsted acid mediated heterogeneous addition reaction of 1,3-dicarbonyl compounds to alkenes and alcohols

(Chemical Equation Presented) The unique acidity of a proton-exchanged montmorillonite catalyst (H-mont) was exploited in the nucleophilic addition of 1,3-dicarbonyl compounds to simple alkenes (see scheme). The benzylation and allylation of 1,3-dicarbony

Highly efficient, reversible addition of activated methylene compounds to styrene derivatives catalyzed by silver catalysts

A highly efficient inter- and intramolecular addition of 1,3-diketone/β-ketoester to alkenes was developed by using silver catalysts. Silver triflate shows the highest catalytic activity. The reaction is reversible through the cleavage of a carbon-carbon bond by silver at an elevated temperature.

Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver

A highly efficient intermolecular addition of 1,3-diketones to alkenes catalyzed by AuCl3/AgOTf was developed. A mechanistic rationale for the reaction has been proposed via a α-C-H activation. Copyright