5337-88-2

Upstream product

• 20970-67-6 1-(5-acetyl-4-phenyl-2,6-dimethyl-1,4-dihydropyridin-3-yl)ethanone 
• 21225-59-2 3,5-diacetyl-4-phenyl-2,6-heptadione 
• 21712-92-5 2-ethoxycarbonylmethyl-2-hydroxy-4-oxo-6-phenyl-cyclohexane-1,3,5-tricarboxylic acid triethyl ester 
• 141-52-6 sodium ethanolate 
• 17572-39-3 2,4-diethoxycarbonyl-5-hydroxy-5-methyl-3-phenylcyclohexanone 
• 141-97-9 ethyl acetoacetate 
• 100-52-7 benzaldehyde 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 75359-71-6 4-phenylheptane-2,6-dione 
• 1165-06-6 Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 144890-17-5 (2,6-Dioxo-4-phenyl-heptyl)-phosphonic acid diethyl ester 
• 96268-73-4 2,4-bis(tert-butoxycarbonyl)-5-hydroxy-5-methyl-3-phenylcyclohexanone 
• 67-64-1 acetone 
• 1896-62-4 (E)-benzalacetone 

Downstream Products

• 3044-71-1 2,6-dimethyl-4-phenylpyridine 
• 62596-11-6 4-methyl-6-phenyl-1,5,6,7-tetrahydro-azepin-2-one 
• 83245-89-0 3-methyl-5-phenyl-cyclohex-2-enone oxime 
• 93468-28-1 5-benzyl-3-methyl-2-cyclohexen-1-one 
• 5114-49-8 6-Hydroxymethylen-3-methyl-5-phenyl-cyclohex-2-en-1-on 
• 60741-75-5 3-methyl-5-phenyl-cyclohexanone 
• 855428-07-8 1-methyl-3-oxo-5-phenyl-cyclohexanecarbonitrile 

Relevant academic research and scientific papers

Iodine-catalyzed tandem oxidative aromatization for the synthesis of meta-substituted alkoxybenzenes

A rapid method for the synthesis of meta-substituted alkoxybenzenes is achieved by oxidation of cyclohexenones. This one-pot transformation is catalyzed by molecular iodine with DDQ as an oxidant in the presence of alcohols. Diverse cyclohexenones with aryl or alkyl substitutes are well tolerated to the mild oxidative conditions affording desired products in up to 92% yield. These oxidizing processes were applicable to the efficient synthesis of useful meta-substituted phenolic products which are difficult to obtain by traditional electrophilic substitutions.

Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide

Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.

Rhodium-catalyzed tandem aldol condensation-Robinson annulation between aldehydes and acetone: Synthesis of 3-methylcyclohexenones

A simple catalytic, redox-neutral access to 3-methylcyclohexenones has been developed via rhodium catalysis in the presence of an amine additive and Ag2CO3. This process utilized simple aldehydes and acetone as substrates and tolerates a variety of functional groups. Disubstituted phenols were isolated in moderate yields when Cu(OAc)2 was employed as an oxidant.

The synthesis of cyclohexenone using l-proline immobilized on a silica gel catalyst by a continuous-flow approach

A facile and convenient method for the synthesis of cyclohexenone compounds was developed using an l-proline immobilized silica gel catalyst combined with a continuous-flow approach. Because of the mild reaction conditions, ease of catalyst recyclability, and product isolation, this reaction approach can potentially be used in a facile scale-up reaction or in industrial applications. the Partner Organisations 2014.

D-Aminoacylase-initiated cascade Aldol condensation/Robinson annulation for synthesis of substituted cyclohex-2-enones from simple aldehydes and acetone

As an important building block, developing efficient and green synthesis strategy of cyclohex-2-enones is of great importance. In this present work, a general approach to the mild synthesis of substituted cyclohex-2-enones derivatives starting fro m simple aldehydes and acetone have been achieved via D-aminoacylase-initiated Aldol condensation/Robinson annulation cascade reaction using imidazole as an additive in organic media. The influences of reaction conditions including solvents, enzyme concentration, additives type, molar ratio of enzyme to additive, and substrate scopes were systematically investigated. Furthermore, some experiments were designed to explore the catalytic roles of D-aminoacylase and imidazole in the multistep cascade process, and one possible mechanism was proposed.

L-Lysine/imidazole-catalyzed multicomponent cascade reaction: Facile synthesis of C5-substituted 3-methylcyclohex-2-enones

A facile and simple route for the direct preparation of substituted 3-methylcyclohex-2-enone via Aldol-Robinson cascade reaction of aldehydes and acetones catalyzed by the new catalytic system of L-lysine/imidazole in n-heptane with 0.5% water was reporte

Effects of dendritic interface on enantioselective catalysis by polymer-bound prolines

Dendritic effects have been observed in the past for a number of metal-based catalysts, but only rarely for organocatalysts, and particularly chiral organocatalysts. In the current study, l-proline was immobilized as an ester or amide on polyether dendritic spacers attached to polystyrene. The ester-including catalysts showed a remarkable positive dendritic effect on yield, but even more so on enantioselectivity, in the aldol reaction of acetone with aromatic aldehydes. The positive dendritic effect of the aforementioned catalytic systems on the yield, diastereo- and enantioselectivity of a three-component Mannich reaction was of an even greater magnitude. A series of experiments marked the possibility of catalysis by homogenous l-proline, detached from the resin during the reaction, highly unlikely. Model comparative studies with catalysts equipped with linear or only partially dendritic spacers emphasized the superiority of the fully dendritic spacer architecture.

Cyclic 2:1 and 1:2 aldehyde-to-acetone byproduct adducts in aldol reactions promoted by supported proline-incorporated catalysts

Significant amounts of cyclic byproducts of aldol addition with stoichiometry deviating from a regular 1:1 addition pattern were formed when the reaction of acetone with aromatic aldehydes was promoted by polymer-supported proline-incorporated catalysts.

An efficient synthesis of some 5-substituted-3-methyl-2-cyclohexen-1-ones using microwaves

3-Methyl-2-cyclohexenone and its 5-substituted-derivatives are prepared in high yields and short duration of time, using the microwave irradiation technique by the condensation of ethyl acetoacetate with eight different aldehydes and piperazine.

Recyclization of 1,4-dihydropyridine derivatives in acidic medium

The recyclization of 1,4-dihydropyridines in aqueous-alcoholic hydrochloric acid medium proceeds with cleavage of a C-N bond and pyridine ring opening. Cyclohexenone derivatives are formed as a result of the subsequent intramolecular crotonic condensation of the acyclic intermediate. The leaving carbonyl substituents depart simultaneously with recyclization, depending on the acidity of the reaction medium.