35490-05-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1246, 1980 DOI: 10.1021/jo01295a017Tetrahedron Letters, 31, p. 4867, 1990 DOI: 10.1016/S0040-4039(00)97754-2

InChI:InChI=1/C10H16O4/c1-4-14-10(13)9(8(3)12)6-5-7(2)11/h9H,4-6H2,1-3H3

Upstream product

• 590-90-9 1-Hydroxy-3-butanone 
• 141-97-9 ethyl acetoacetate 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 1721-13-7 ethyl 2,6-dimethylnicotinate 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 14619-42-2 ethyl 4-methyl-2-oxocyclohex-3-ene-1-carboxylate 
• 1193-18-6 3-methylcyclohexen-2-one 
• 49748-84-7 6-n-butyl-3-methyl-2-cyclohexenone 
• 71898-95-8 3-Methyl-6-(2-methylbut-2-enyl)cyclohex-2-enon 
• 27242-99-5 6-isopentyl-3-methyl-cyclohex-2-enone 
• 71898-92-5 6-n-Pentyl-3-methyl-cyclohex-2-en-1-on 
• 71898-93-6 6-Hexyl-3-methylcyclohex-2-enon 
• 71898-91-4 1-butyl-4-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 1033362-96-7 ethyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-phenyl-cyclohexanecarboxylate 
• 1033363-00-6 ethyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-p-tolyl-cyclohexanecarboxylate 
• 1033363-12-0 ethyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-(2-nitrophenyl)cyclohexanecarboxylate 
• 1033362-98-9 ethyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-2-(4-methoxyphenyl)-4-methyl-3-nitrocyclohexanecarboxylate 

Relevant academic research and scientific papers

Synthesis of fused quinolizine derivatives by condensation of cyclic schiff bases with β-keto esters

A new procedure has been developed for the synthesis of fused nitrogen-containing heterocycles having a bridgehead nitrogen atom via condensation of cyclic Schiff bases with β-keto esters.

Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides

The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reaction

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.

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.

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

We have discovered synthetic access to β-hydroperoxy-β-peroxylactones via BF3-catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals, with H2O2. Strikingly, independent of the choice of starting material, these reactions converge at the same β-hydroperoxy-β-peroxylactone products, i.e., the peroxy analogues of the previously elusive cyclic Criegee intermediate of the Baeyer-Villiger reaction. Computed thermodynamic parameters for the formation of the β-hydroperoxy-β-peroxylactones from silyl enol ethers, enol acetates, and cyclic acetals confirm that the β-peroxylactones indeed correspond to a deep energy minimum that connects a variety of the interconverting oxygen-rich species at this combined potential energy surface. The target β-hydroperoxy-β-peroxylactones were synthesized from β-ketoesters, and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals were obtained in 30-96% yields. These reactions proceed under mild conditions and open synthetic access to a broad selection of β-hydroperoxy-β-peroxylactones that are formed selectively even in those cases when alternative oxidation pathways can be expected. These β-peroxylactones are stable and can be useful for further synthetic transformations.

Bimetallic Oriented (Au/Cu2O) vs. Monometallic 1.1.1 Au (0) or 2.0.0 Cu2O Graphene-Supported Nanoplatelets as Very Efficient Catalysts for Michael and Henry Additions

Michael and Henry addition reactions have been investigated using mono (Au and Cu2O) and bimetallic nanoplatelets (Au/Cu2O) grafted onto few-layers graphene (fl-G) films as heterogeneous catalysts by comparison with homogeneous NaOH and K2CO3 ones. In the presence of the heterogeneous catalysts, these reactions occurred in the absence of any extrinsic (NaOH and K2CO3) base with turnover numbers (TONs) at least four orders of magnitude higher. While the homogeneous catalysts provided TONs close to the unity for Au/Cu2O/fl-G this was of the order of 107. These reactions also occurred with a very good selectivity to the targeted products. These performances are in line with the basicity of these catalysts demonstrated from CO2 chemisorption measurements. The effect of the nanosize and the interaction of the nanoparticles with the graphene are also important to achieve this high activity.

SYNTHESIS OF FURAN, THIOPHENE, AND PYRROLES FROM ACETOACETIC ESTERS

The present invention refers to using ester pgd2 alkylacetoacetoates furan, thiophene, method relates to synthesis of pyrrole, more particularly the acetohydroxy pgd2 ester compound alpha, beta unsaturated carbonyl compounds obtained is added to the 1,5-dicarbonyl compounds (II)/ cobalt manganese (III) method of silica glass by sol the reaction deacetylase with Neel step then alkali to thereby synthesize a compound 1,4-dicarboxylic, Paal-Knorr herein using synthesis on the furan, thiophene, pyrrole for synthesizing relates to method. According to the present invention, a necessary for synthesis of Paal-Knorr 1,4-dicarbonyl compounds efficiently mixed in the oxidation reaction from said 1,5-dicarbonyl compounds (deacetylase reaction) and a conjunction synthesis on the Paal-Knorr in the reaction vessel a are sequentially two reactors furan, thiophene, and of won-port synthesis method by using the mask pattern.. (by machine translation)

Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is

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).

Metal-dioxidoterephthalate MOFs of the MOF-74 type: Microporous basic catalysts with well-defined active sites

The hybrid frameworks M2dobdc (dobdc4- = 2,5-dioxidoterephthalate, M2+ = Mg2+, Co2+, Ni2+, Cu2+ and Zn2+), commonly known as CPO-27 or MOF-74, are shown to be active catalysts in base-catalyzed reactions such as Knoevenagel condensations or Michael additions. Rather than utilizing N-functionalized linkers as a source of basicity, the intrinsic basicity of these materials arises from the presence of the phenolate oxygen atoms coordinated to the metal ions. The overall activity is due to a complex interplay of the basic properties of these structural phenolates and the reactant binding characteristics of the coordinatively unsaturated sites. The nature of the active site and the order of activity between the different M 2dobdc materials were rationalized via computational efforts; the most active material, both in theory and in experiment, is the Ni-containing variant. The basicity of Ni2dobdc was experimentally proven by chemisorption of pyrrole and observation by IR spectroscopy.