13395-76-1

Usage

Uses

Used in Flavoring Agents:
2,3-dimethylcyclohexan-1-one serves as a flavoring agent in the food and beverage industry, leveraging its pleasant aroma and taste to enhance the sensory experience of various products.
Used in Synthesis of Organic Compounds and Pharmaceuticals:
Beyond its role in flavoring, 2,3-dimethylcyclohexan-1-one functions as an intermediate in the synthesis of a range of organic compounds and pharmaceuticals, contributing to the development of new chemical entities and medicines.
Used in Chemical Manufacturing:
In the chemical manufacturing industry, 2,3-dimethylcyclohexan-1-one is utilized for its properties that make it a valuable component in the production of various chemical products, including fragrances and other specialty chemicals.
It is crucial to handle and store 2,3-dimethylcyclohexan-1-one with care due to its flammability and potential to cause skin and eye irritation, ensuring safety in its applications across different industries.

InChI:InChI=1/C8H14O/c1-6-4-3-5-8(9)7(6)2/h6-7H,3-5H2,1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 52456-90-3 6-methyl-2-hydroxycyclohexanone 
• 1122-20-9 2,3-dimethylcyclohex-2-en-1-one 
• 17082-05-2 (E)-1-nitroprop-1-ene 
• 2004-70-8 1-methylbuta-1,3-diene 
• 39256-98-9 oct-7-en-3-one 
• 1502-24-5 2,3-dimethylcyclohexan-1-ol 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 917-54-4 methyllithium 
• 74173-18-5 trimethyl(3-methylcyclohex-1-enyloxy)silane 
• 74-88-4 methyl iodide 
• 583-57-3 1,2-Dimethyl-cyclohexane 
• 930-68-7 cyclohexenone 

Downstream Products

• 106591-61-1 2,3-dimethyl-6-phenoxy-cyclohexanone 
• 3864-18-4 2,3-dimethyl-1,1'-biphenyl 
• 18707-82-9 1-Phenyl-2,3-dimethyl-cyclohexanol 
• 73328-30-0 6-hydroxymethylene-2,3-dimethylcyclohexanone 
• 98361-28-5 2,3-dimethyl-1-trimethylsilyloxycyclohexene 
• 139697-56-6 3,4-Dimethyl-2-trimethylsiloxycyclohex-1-ene 
• 75306-21-7 (1-Hydroxy-2,3-dimethyl-cyclohexyl)-acetic acid ethyl ester 
• 133304-85-5 2-hydroxy-3,4-dimethyl-2-cyclohexenone 
• 294210-46-1 3,4-dimethyl-2-oxo-cyclohexanecarbaldehyde 

Relevant academic research and scientific papers

Total Synthesis of Paralemnolide A

The first total synthesis of tricyclic bisnorsesquiterpene paralemnolide A, isolated from the soft coral Paralemnalia thyrsoides, was achieved. This synthesis features the lactonization of the cyclohexene derivative having a tert-butyl ester via stereosel

The Use of Silyl Enol Ethers in the Alkylation of Substituted Cyclanones.

The reactions of 1-(trimethylsiloxy)-3-methylcyclopent-1-ene, 1-(trimethylsiloxy)-3-methylcyclohex-1-ene and 1-(trimethylsiloxy)-3,3-dimethylcyclohex-1-ene with various alkylating agents in the presence of silver trifluoroacette produced the corresponding

The total synthesis of the new sesquiterpenoid (±)-fulvanin 1/sollasin a

The reaction of 2,3-dimethylcyclohexan-1-one (2) with the functionalized allylic bromide 3 produced regio- and stereoselectively a precursor (4) of the new sesquiterpenoid sollasin a/fulvanin 1 (1). Functional group transformations then completed the synt

Catalytic oxidation of alkanes by iron bispidine complexes and dioxygen: Oxygen activation versus autoxidation

Organic substrates (specifically cis-1,2-dimethylcyclohexane, DMCH) are oxidized by O2 in the presence of iron(ii)-bispidine complexes. It is shown that this oxidation reaction is not based on O2 activation by the nonheme iron catalysts as in Nature but due to a radical-based initiation, followed by a radical- and ferryl-based catalytic reaction.

Oxidation of Alkanes by Periodate Using a MnV Nitrido Complex as Catalyst

The design of catalytic systems that can selectively oxidize unactivated C?H bonds under mild conditions is a challenge to chemists. We report here that the manganese(V) nitrido complex [MnV(N)(CN)4]2? is a highly efficient catalyst for the oxidation of alkanes by periodate (IO4 ?) at ambient conditions. Excellent yields of alcohols and ketones (>95 %) are obtained with a maximum turnover number (TON) of 3000.

From DNA to catalysis: A thymine-acetate ligated non-heme iron(III) catalyst for oxidative activation of aliphatic C-H bonds

A non-heme, iron(iii)/THA(thymine-1-acetate) catalyst together with H2O2 as an oxidant is efficient in oxidative C-H activation of alkanes. Although having a higher preference for tertiary C-H bonds, the catalyst also oxidizes aliphatic secondary C-H bonds into carbonyl compounds with good to excellent conversions. Based on the site selectivity of the catalyst and our mechanistic studies the reaction proceeds via an Fe-oxo species without long lived carbon centered radicals.

Catalytic Oxidation of Alkanes and Alkenes by H2O2 with a μ-Oxido Diiron(III) Complex as Catalyst/Catalyst Precursor

A new μ-oxo diiron(III) complex of the lithium salt of the pyridine-based unsymmetrical ligand 3-[(3-{[bis(pyridin-2-ylmethyl)amino]methyl}-2-hydroxy-5-methylbenzyl)(pyridin-2-ylmethyl)amino]propanoate (LiDPCPMPP), [Fe2(μ-O)(LiDPCPMPP)2](ClO4)2, has been synthesized and characterized. The ability of the complex to catalyze oxidation of several alkanes and alkenes has been investigated by using CH3COOH/H2O2 (1:1) as an oxidative system. Moderate activity in cyclohexane oxidation (TOF = 33 h-1) and good activity in cyclohexene oxidation (TOF = 72 h-1) were detected. Partial retention of configuration (RC = 53%) in cis- and trans-1,2-dimethylcyclohexane oxidation, moderate 3/2 selectivity (4.1) in adamantane oxidation, and the observation of a relatively high kinetic isotope effect for cyclohexane oxidation (KIE = 3.27) suggest partial metal-based oxidation, probably in tandem with free-radical oxidation. Low-temperature UV/Vis spectroscopy and mass spectrometric studies in the rapid positive detection mode indicate the formation of a transient peroxido species, [Fe2(O)(O2)(LiDPCPMPP)2]2+, which might be an intermediate in the metal-based component of the oxidation process. A μ-oxido diiron(III) complex, [Fe2(μ-O)(LiDPCPMPP)2](ClO4)2, was synthesized and characterized. This complex was used as catalyst in C-H bond oxidation with CH3COOH-H2O2 as chemical oxidant. Reactivity studies indicate that the oxidation process goes through a metal-based mechanism concomitant with a radical process.

Copper-catalysed conjugate addition of grignard reagents to 2-methylcyclopentenone and sequential enolate alkylation

The copper/Rev-JosiPhos-catalysed asymmetric conjugate addition of Grignard reagents to 2-methylcyclopentenone (1) provides 2,3-disubstituted cyclopentanones in high yields and enantioselectivities, and good diastereoselectivities. Reaction of the in situ

Highly efficient alkane oxidation catalyzed by [MnV(N)(CN) 4]2-. Evidence for [MnVII(N)(O)(CN) 4]2- as an active intermediate

The oxidation of various alkanes catalyzed by [MnV(N)(CN) 4]2- using various terminal oxidants at room temperature has been investigated. Excellent yields of alcohols and ketones (>95%) are obtained using H2O2 as oxidant and CF3CH 2OH as solvent. Good yields (>80%) are also obtained using (NH4)2[Ce(NO3)6] in CF 3CH2OH/H2O. Kinetic isotope effects (KIEs) are determined by using an equimolar mixture of cyclohexane (c-C6H 12) and cyclohexane-d12 (c-C6D12) as substrate. The KIEs are 3.1 ± 0.3 and 3.6 ± 0.2 for oxidation by H2O2 and Ce(IV), respectively. On the other hand, the rate constants for the formation of products using c-C6H12 or c-C6D12 as single substrate are the same. These results are consistent with initial rate-limiting formation of an active intermediate between [Mn(N)(CN)4]2- and H2O2 or CeIV, followed by H-atom abstraction from cyclohexane by the active intermediate. When PhCH2C(CH3)2OOH (MPPH) is used as oxidant for the oxidation of c-C6H12, the major products are c-C6H11OH, c-C6H10O, and PhCH2C(CH3)2OH (MPPOH), suggesting heterolytic cleavage of MPPH to generate a Mn=O intermediate. In the reaction of H2O2 with [Mn(N)(CN)4]2- in CF 3CH2OH, a peak at m/z 628.1 was observed in the electrospray ionization mass spectrometry, which is assigned to the solvated manganese nitrido oxo species, (PPh4)[Mn(N)(O)(CN)4] -·CF3CH2OH. On the basis of the experimental results the proposed mechanism for catalytic alkane oxidation by [MnV(N)(CN)4]2-/ROOH involves initial rate-limiting O-atom transfer from ROOH to [Mn(N)(CN)4]2- to generate a manganese(VII) nitrido oxo active species, [MnVII(N)(O) (CN)4]2-, which then oxidizes alkanes (R'H) via a H-atom abstraction/O-rebound mechanism. The proposed mechanism is also supported by density functional theory calculations.

A ring contraction strategy toward a diastereoselective total synthesis of (+)-bakkenolide A

A diastereoselective route to (+)-bakkenolide A is presented from the readily available optically active Wieland-Miescher ketone. This novel synthesis of this sesquiterpene lactone features the following as key stereoselective transformations: (i) the ring contraction reaction of a octalone mediated by thallium(III) nitrate (TTN); (ii) a hydrogenation to create the cis-fused junction; and (iii) the formation of the C7 quaternary center through an enolate intermediate. Furthermore, during this work, the absolute configuration of a trinorsesquiterpene isolated from Senecio Humillimus was assigned.