77548-32-4

Basic information

• Product Name: ethyl 2-acetyl-5-oxo-3-phenylhexanoate
• Synonyms: ethyl 2-acetyl-5-oxo-3-phenylhexanoate
• CAS NO: 77548-32-4
• Molecular Weight: 276.332
• Mol File: 77548-32-4.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2-acetyl-5-oxo-3-phenylhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-acetyl-5-oxo-3-phenylhexanoate(77548-32-4)
• EPA Substance Registry System: ethyl 2-acetyl-5-oxo-3-phenylhexanoate(77548-32-4)

Safety Data

• Hazardous Substances Data: 77548-32-4(Hazardous Substances Data)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 

Relevant articles and documents

Electrochemically responsive heterogeneous catalysis for controlling reaction kinetics

We report a method to control reaction kinetics using electrochemically responsive heterogeneous catalysis (ERHC). An ERHC system should possess a hybrid structure composed of an electron-conducting porous framework coated with redox-switchable catalysts. In contrast to other types of responsive catalysis, ERHC combines all the following desired characteristics for a catalysis control strategy: continuous variation of reaction rates as a function of the magnitude of external stimulus, easy integration into fixed-bed flow reactors, and precise spatial and temporal control of the catalyst activity. Herein we first demonstrate a facile approach to fabricating a model ERHC system that consists of carbon microfibers with conformal redox polymer coating. Second, using a Michael reaction whose kinetics depends on the redox state of the redox polymer catalyst, we show that use of different electrochemical potentials permits continuous adjustment of the reaction rates. The dependence of the reaction rate on the electrochemical potential generally agrees with the Nernstian prediction, with minor discrepancies due to the multilayer nature of the polymer film. Additionally, we show that the ERHC system can be employed to manipulate the shape of the reactant concentration-time profile in a batch reactor through applying customized potential-time programs. Furthermore, we perform COMSOL simulation for an ERHC-integrated flow reactor, demonstrating highly flexible manipulation of reactant concentrations as a function of both location and time. (Chemical Equation Presented).

Efficient microwave activation of hydrotalcite clays in Michael addition under solvent-free conditions

Microwave irradiation has been successfully utilized for the first time for the activation of unmodified hydrotalcites (HTs, a basic anionic clay), in the Michael addition reaction between enones and active methylenic compounds under solventless condition

ZrCl4-catalyzed Michael reaction of 1,3-dicarbonyls and enones under solvent-free conditions

ZrCl4 has been found to catalyze the conjugate addition of 1,3-dicarbonyl compounds with enones. The reaction does not require any solvent and proceeds smoothly at room temperature leading to the corresponding adduct in good yields.

New Application of 1,4-Dihydropyridine System: Michael Reactions Mediated by 1,4-Dihydropyridine-Enolate Adduct in Micellar Medium

1,4-dihydropyridine-acetophenone enolate adduct, in catalytic amount effects Michael reactions in aqueous cationic micelles of cetyltrimethylammonium bromide. The enolate, generated by dissociation of the adduct abstracts a proton from readily enolizable substrates to bring about the Michael reaction under mild conditions in fair to good yields without side products.

Cu(II)-catalyzed Michael addition of 1,3-dicarbonyl compounds

Copper sulphate pentahydrate catalyses the C-C bond formation via Michael addition of 1,3-dicarbonyl compounds 1 under mild and neutral conditions at ambient temperature and furnishes the products 3 in high yields.

Novel chemoselective and diastereoselective iron(III)-catalysed Michael reactions of 1,3-dicarbonyl compounds and enones

Iron(III) chloride hexahydrate catalyses the Michael reaction of 1,3-dicarbonyl compounds with α,β-unsaturated ketones under mild and neutral conditions with extraordinary efficiency. The chemoselectivity of this FeIII-catalysed process is superior to that of the classic base-catalysed Michael reaction, since the latter suffers from various side reactions, namely drawbacks such as aldol cyclisations and ester solvolysis. Excellent yields and chemoselectivities together with the environmentally friendly nature of FeIII catalysis makes this an important alternative to classic base catalysis. Moreover, the reaction procedure is reasonably easy: FeIII catalysis does not require inert or anhydrous conditions, and in most cases no solvent is needed. In terms of diastereoselectivity, the FeIII-mediated reaction may also prove superior to a base-catalysed one. In at least one example, FeIII catalysis forms a diastereoisomer as the major kinetic product, which is disfavoured in the base-mediated Michael reaction, where a thermodynamic mixture is obtained. The relative configuration of the diastereoisomeric Michael products has been determined for two examples by synthesis and structure elucidation of the cyclic aldol derivatives.

Lanthanides in organic synthesis: Eu+3-catalyzed Michael addition of 1,3-dicarbonyl compounds

EuCl3 proves to be an efficient catalyst for Michael addition of 1,3-dicarbonyl compounds. The employment of Eu+3 chiral complex [Eu(tfc)3] allows the formation of Michael adducts in enantioselective way.

Dual catalysis of the Michael reaction

The Michael reaction, with conjugate bases of β-diketones as donors and with α,β-unsaturated ketones as acceptors, is efficiently catalyzed by a combination of clay-supported nickel bromide (heterogeneous) and ferric chloride (homogeneous).