151330-38-0

Basic information

• Product Name: 2-benzoyl-1-phenylhexane-1,5-dione
• Synonyms: 2-benzoyl-1-phenylhexane-1,5-dione
• CAS NO: 151330-38-0
• Molecular Weight: 294.35
• Mol File: 151330-38-0.mol

Chemical Properties

• CAS DataBase Reference: 2-benzoyl-1-phenylhexane-1,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzoyl-1-phenylhexane-1,5-dione(151330-38-0)
• EPA Substance Registry System: 2-benzoyl-1-phenylhexane-1,5-dione(151330-38-0)

Safety Data

• Hazardous Substances Data: 151330-38-0(Hazardous Substances Data)

Upstream product

• 397-85-3 dibenzoylmethanatoboron difluoride 
• 78-94-4 methyl vinyl ketone 
• 120-46-7 1,3-diphenylpropanedione 
• 598-32-3 2-hydroxy-3-butene 

Relevant articles and documents

Silica gel-mediated catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to highly toxic methyl vinyl ketone without volatilization

Silica gel-mediated Michael addition of 1,3-dicarbonyl compounds to methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) was carried out to give the corresponding adducts in quite excellent yields. The reactions could be carried out without any catalysts and solvents. In addition, highly toxic MVK and EVK could be employed without significant volatilization. Silica gel could be recycled five times without the decrease of the yields.

Preparation of a microsized cerium chloride-based catalyst and its application in the Michael addition of β-diketones to vinyl ketones

A facile method, which does not require special equipment, was developed for the preparation of microsized cerium chloride by the thermal treatment of CeCl3·7H2O or the evaporation of its alcoholic solutions. The way of the preparation of the cerium chloride-based catalyst plays a decisive role in its catalytic activity. This catalyst is efficient in the Michael addition of β-diketones to vinyl ketones giving β,δ-triketones.

Polymer-incarcerated gold-palladium nanoclusters with boron on carbon: A mild and efficient catalyst for the sequential aerobic oxidation-Michael addition of 1,3-dicarbonyl compounds to allylic alcohols

We have developed a polymer-incarcerated bimetallic Au-Pd nanocluster and boron as a catalyst for the sequential oxidation-addition reaction of 1,3-dicarbonyl compounds with allylic alcohols. The desired tandem reaction products were obtained in good to excellent yields under mild conditions with broad substrate scope. In the course of our studies, we discovered that the excess reducing agent, sodium borohydride, reacts with the polymer backbone to generate an immobilized tetravalent boron catalyst for the Michael reaction. In addition, we found bimetallic Au-Pd nanoclusters to be particularly effective for the aerobic oxidation of allylic alcohols under base- and water-free conditions. The ability to conduct the reaction under relatively neutral and anhydrous conditions proved to be key in maintaining good catalyst activity during recovery and reuse of the catalyst. Structural characterization (STEM, EDS, SEM, and N2 absorption/desorption isotherm) of the newly prepared PI/CB-Au/Pd/B was performed and compared to PI/CB-Au/Pd. We found that while boron was important for the Michael addition reaction, it was found to alter the structural profile of the polymer-carbon black composite material to negatively affect the allylic oxidation reaction.

Hydrogen-bond-promoted C-C bond-forming reaction: Catalyst-free Michael addition reactions in ethanol

A practical protocol for catalyst-free Michael addition reactions in ethanol was developed. The reaction was promoted efficiently in alcohol without any additives, and the importance of hydrogen-bonding activation was suggested. Georg Thieme Verlag Stuttg

Neutral Lewis bases as activators of molecular sieves in the conjugate addition of 1,3-dicarbonyl compounds

The catalytic properties of 3 A molecular sieves in the promotion of Michael addition of 1,3-dicarbonyl compounds are significantly improved by activation with several neutral Lewis bases. Comparable efficiency can be observed under solvent-free condition

Organocatalytic transformation of 1,3-diketones into optically active cyclohexanones

The domino Michael-aldol reaction of 1,3-diketones with MVK in the presence of L-proline furnished highly substituted cyclohexanones in a regio- and stereocontrolled manner. When the reaction was performed in NMP, high yields (up to 93%) and enantioselectivities up to 80% were observed.

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.

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.

The photocycloaddition of dibenzoylmethanatoboron difluoride (DBMBF2) with conjugated enones and en-esters

Dibenzoylmethanatoboron difluoride (DBMBF2), the BF2 complex of dibenzoylmethane, reacted from its singlet excited state with α,β-unsaturated ketones and esters to give 1,5-diketones by a cycloaddition and ring-opening sequence in an analogous pathway to that observed in the photocycloaddition to olefins and dienes.The present photoreaction is unexpected since conjugated enones and en-esters are poor electron donors to comply with the previously proposed charge transfer requirement in DBMBF2 photoreactions.The photocycloaddition to these substrates was highly regioselective and stereoselective, giving the head-to-head orientation, which could be enhanced by α-methyl substitution; β-methyl substitution increased the alternate head-to-tail orientation.The photolysis of a mixture of DBMBF2 and a cyclic enone also caused the latter to dimerize to give head-to-head and head-to-tail dimers in significant yields.These photodimerizations were apparently caused by DBMBF2 sensitization.The mechanism of the sensitization is discussed.