2979-19-3

Usage

Uses

Used in Chemical Synthesis:
3,3-Dimethylcyclohexanone is used as a starting material for the synthesis of boll weevil sex attractants. It plays a crucial role in the development of these attractants due to its unique chemical structure, which allows for further reactions and modifications to create the desired end product.
Used in Pest Control Industry:
In the pest control industry, 3,3-Dimethylcyclohexanone is used as a precursor in the production of pheromones that are specifically designed to attract and control boll weevils. These pheromones are used in integrated pest management strategies to monitor and manage boll weevil populations, reducing the need for chemical pesticides and promoting more sustainable agricultural practices.
Used in Research and Development:
3,3-Dimethylcyclohexanone is also used in research and development for the exploration of alternative syntheses and the creation of new compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science. Its versatility as a starting material makes it a valuable asset in the development of innovative products and solutions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 3619, 1975 DOI: 10.1021/jo00912a040

InChI:InChI=1/C8H14O/c1-8(2)5-3-4-7(9)6-8/h3-6H2,1-2H3

Upstream product

• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 917-64-6 methyl magnesium iodide 
• 1193-18-6 3-methylcyclohexen-2-one 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 64-17-5 ethanol 
• 102942-81-4 1-hydroxy-3,3-dimethyl-cyclohexanecarbonitrile 
• 767-12-4 3,3-dimethylcyclohexanol 
• 54200-63-4 2-acetyl-3,3-dimethylcyclohexanone 
• 917-54-4 methyllithium 
• 75-24-1 trimethylaluminum 
• 1184-53-8 methylcopper 
• 61675-01-2 6-bromo-4,4-dimethyl-hexan-2-one 
• 15681-48-8 lithium dimethylcuprate 
• 50337-09-2 2,4-Dibrom-1,1-dimethyl-cyclohexanon-⁽³⁾ 

Downstream Products

• 79802-79-2 1,3,3-trimethyl-cyclohexan-1-ol 
• 102942-81-4 1-hydroxy-3,3-dimethyl-cyclohexanecarbonitrile 
• 61592-59-4 2-acetoxy-5,5-dimethyl-cyclohexanone 
• 848760-72-5 1-ethyl-3,3-dimethyl-cyclohexanol 
• 767-12-4 3,3-dimethylcyclohexanol 
• 15189-14-7 2,2,5,5-tetramethylcyclohexanone 
• 3100-85-4 5,5-dimethyl-2-bromocyclohexanone 
• 2979-20-6 3,3-dimethyl-cyclohexanone semicarbazone 
• 24636-47-3 2-acetyl-5,5-dimethyl-cyclohexanone 
• 5629-80-1 (1-hydroxy-3,3-dimethyl-cyclohexyl)-acetic acid ethyl ester 
• 57559-98-5 1-ethynyl-3,3-dimethylcyclohexan-1-ol 
• 36168-42-0 4,4-dimethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 41370-30-3 Boll Weevil pheromone 
• 54200-64-5 1-acetoxy-3,3-dimethylcyclohexene 

Relevant academic research and scientific papers

Fragmentation-cyclization reactions by photoinduced electron transfer

Irradiation of unsaturated bicyclo[4.1.0]heptanones and bicyclo[3.1.0]hexanones under reductive PET conditions leads to a regioselective cleavage of the cyclopropane moiety followed by cyclization. By this method various types of ring anellated and spirocyclic compounds are accessible.

A gatekeeper residue for inhibitor sensitization of protein tyrosine phosphatases

Allele-specific enzyme inhibitors are powerful tools in chemical biology. However, few general approaches for the discovery of such inhibitors have been described. Herein is reported a method for the sensitization of protein tyrosine phosphatases (PTPs) to small-molecule inhibition. It is shown that mutation of an active-site isoleucine to alanine (I219A) sensitizes PTP1B to inhibition by a class of thiophene-based inhibitors. This sensitization strategy succeeds for both 'orthogonal' inhibitors, designed to be incompatible with wild-type PTP active sites, and previously optimized wild-type PTP inhibitors. The finding that the I219A mutation sensitizes phosphatase domains to a variety of compounds suggests that isoleucine 219 may act as a 'gatekeeper' residue that can be widely exploited for the chemical-genetic analysis of PTP function.

Potential inhibitors of collagen biosynthesis. 5,5-Difluoro-DL-lysine and 5,5-dimethyl-DL-lysine and their activation by lysyl-tRNA ligase

The synthesis of lysine analogues wherein blocking groups are substituted at position 5, the site of hydroxylation by peptidyl lysine hydroxylase, is described. Thus, 5,5-diflurolysine (1) and 5,5-dimethyllysine (2) were synthesized via a four- and six-step sequence, respectively, starting from ketone precursors. The propensity for these lysine analogues to be incorporated into procollagen protein in vivo was assessed by their ability to stimulate the lysine-dependent ATP-PP(i) exchange reaction in the presence of lysyl-tRNA ligase in vitro. The difluoro analogue 1 stimulated exchange, but at a K(m) (1.3 x 10-3 M) 1000 times greater than that for lysine itself. The dimethyl analogue 2 did not stimulate exchange, but at high concentrations was a competitive inhibitor of lysine, with an apparent K(i) of 1.6 x 10-2 M. Thus, electronegative and/or bulky substituents at the 5 position of lysine cannot be tolerated by lysyl-tRNA ligase, and this position must be kept free in lysine analogues specifically designed to block collagen biosynthesis.

Reduction of α,β-unsaturated carbonyl compounds and 1,3-diketones in aqueous media, using a raney ni-al alloy

The treatment of α,β-unsaturated carbonyl compounds and 1,3-diketones with Raney Ni-Al alloy in aqueous media yielded as major reaction products the corresponding saturated alcohols and/or the corresponding hydrocarbons, in a complete transformation of the starting material.

Reduction of α,β-Unsaturated carbonyl compounds and 1,3-Diketones in aqueous media, using a raney ni-al alloy

The treatment of α,β-unsaturated carbonyl compounds and 1,3-diketones with Raney Ni-Al alloy in aqueous media yielded as major reaction products the corresponding saturated alcohols and/or the corresponding hydrocarbons, in a complete transformation of the starting material.

A method for synthesis of 3, 3 - dimethyl cyclohexanone (by machine translation)

The present application relates to the field of drug synthesis, in particular, relates to 3, 3 - dimethyl cyclohexanone a synthesizing method of. The invention synthetic method mild reaction conditions, easy to enlarge production; the various reagent are on the market are easy, and the cost is low; effectively through the intermediate step of the oxidation reaction of the by-product 3, 3 - dimethyl cyclohexanol turns into the product 3, 3 - dimethyl cyclohexanone. Improves the yield, and reduces the difficulty of the purification. (by machine translation)

Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions

An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.

Catalyst-controlled aliphatic C—H oxidations

The invention provides simple small molecule, non-heme iron catalyst systems with broad substrate scope that can predictably enhance or overturn a substrate's inherent reactivity preference for sp3-hybridized C—H bond oxidation. The invention also provides methods for selective aliphatic C—H bond oxidation. Furthermore, a structure-based catalyst reactivity model is disclosed that quantitatively correlates the innate physical properties of the substrate to the site-selectivities observed as a function of the catalyst. The catalyst systems can be used in combination with oxidants such as hydrogen peroxide to effect highly selective oxidations of unactivated sp3 C—H bonds over a broad range of substrates.

Aerobic oxidation of secondary alcohols in water with ABNO/tert-butyl nitrite/KPF6catalytic system

A green and efficient transition-metal free ABNO/tert-butyl nitrite/KPF6-catalyzed aerobic oxidation of secondary alcohols in water has been achieved. Under the optimal reaction conditions, a number of secondary aliphatic alcohols and secondary benzylic alcohols can be converted to their corresponding ketones in excellent yields (up to 99%).

Readily Accessible Bulky Iron Catalysts exhibiting Site Selectivity in the Oxidation of Steroidal Substrates

Bulky iron complexes are described that catalyze the site-selective oxidation of alkyl C-H bonds with hydrogen peroxide under mild conditions. Steric bulk at the iron center is introduced by appending trialkylsilyl groups at the meta-position of the pyridines in tetradentate aminopyridine ligands, and this effect translates into high product yields, an enhanced preferential oxidation of secondary over tertiary C-H bonds, and the ability to perform site-selective oxidation of methylenic sites in terpenoid and steroidal substrates. Unprecedented site selective oxidation at C6 and C12 methylenic sites in steroidal substrates is shown to be governed by the chirality of the catalysts.