18022-66-7

Usage

Uses

3,4-DIMETHYL-3-CYCLOHEXENYLMETHANAL is used as a chemical intermediate for the synthesis of various secondary amine compounds. These compounds are particularly useful as tRNA synthetase inhibitors, which play a crucial role in the development of new antimicrobial agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-DIMETHYL-3-CYCLOHEXENYLMETHANAL is used as a key component in the preparation of tRNA synthetase inhibitors. These inhibitors are specifically designed to target and disrupt the function of tRNA synthetase enzymes in Gram-negative bacteria, thereby inhibiting their growth and proliferation. This makes them a promising avenue for the development of new antibiotics to combat drug-resistant bacterial infections.
Additionally, 3,4-DIMETHYL-3-CYCLOHEXENYLMETHANAL may also find applications in other industries, such as the fragrance and flavor industry, due to its strong and distinctive odor.

Upstream product

• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 107-02-8 acrolein 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 39155-41-4 (3,4-dimethylcyclohex-3-en-1-yl)methanol 
• 2952-87-6 1-(3,4-Dimethyl-cyclohex-3-enyl)-but-3-en-1-ol 
• 74235-35-1 3.4-Dimethyl-3-cyclohexen-1.1-dimethanol 
• 74454-23-2 1-(3,4-dimethyl-cyclohex-3-enyl)-propan-1-ol 
• 74454-07-2 4-(1-acetoxy-ethyl)-1,2-dimethyl-cyclohexene 
• 74454-12-9 4-(1-acetoxy-propyl)-1,2-dimethyl-cyclohexene 
• 95-47-6 o-xylene 
• 95-63-6 1,2,4-Trimethylbenzene 
• 1674-10-8 1,2-dimethylcyclohexene 
• 90769-69-0 1,2,4-trimethylcyclohex-1-ene 
• 119336-62-8 (4R,6R)-2-((R)-3,4-Dimethyl-cyclohex-3-enyl)-4,6-dimethyl-[1,3]dioxane 
• 119336-62-8 (4R,6R)-2-((S)-3,4-Dimethyl-cyclohex-3-enyl)-4,6-dimethyl-[1,3]dioxane 

Relevant academic research and scientific papers

Sustainable Production of o-Xylene from Biomass-Derived Pinacol and Acrolein

o-Xylene (OX) is a large-volume commodity chemical that is conventionally produced from fossil fuels. In this study, an efficient and sustainable two-step route is used to produce OX from biomass-derived pinacol and acrolein. In the first step, the phosphotungstic acid (HPW)-catalyzed pinacol dehydration in 1-ethyl-3-methylimidazolium chloride ([emim]Cl) selectively affords 2,3-dimethylbutadiene. The high selectivity of this reaction can be ascribed to the H-bonding interaction between Cl? and the hydroxy group of pinacol. The stabilization of the carbocation intermediate by the surrounding anion Cl? may be another reason for the high selectivity. Notably, the good reusability of the HPW/[emim]Cl system can reduce the waste output and production cost. In the second step, OX is selectively produced by a Diels–Alder reaction of 2,3-dimethylbutadiene and acrolein, followed by a Pd/C-catalyzed decarbonylation/aromatization cascade in a one-pot fashion. The sustainable two-step process efficiently produces renewable OX in 79 % overall yield. Analogously, biomass-derived crotonaldehyde and pinacol can also serve as the feedstocks for the production of 1,2,4-trimethylbenzene.

Poly(ethylene glycol)-Supported Chiral Imidazolidin-4-one: An Efficient Organic Catalyst for the Enantioselective Diels-Alder Cycloaddition

A tyrosine-derived imidazolidin-4-one was immobilized on a modified poly(ethylene glycol) and converted in situ into a soluble polymer-supported catalyst for the enantioselective Diels-Alder cycloaddition of acrolein to 1,3-cyclohexadiene (up to 92% ee) a

On the Use of Ferrocenyl Cations as Chiral Lewis Acids: Evidence for Protic Acid Catalysis

The preparation of cation 1 is described, as is the use of this material as a catalyst in the Diels-Alder reaction.While the addition of 1 does promote the Diels-Alder reaction, it is not the catalytic species.Rather, it acts as a source of protic acid wh

Polyesters Containing Chiral Imidazolidinone Salts in Polymer Main Chain: Heterogeneous Organocatalysts for the Asymmetric Diels–Alder Reaction

Novel main-chain polyesters functionalized with chiral imidazolidinone salts were successfully synthesized. Polycondensation of a chiral imidazolidinone dimer bearing two hydroxyphenyl groups with selected achiral dicarboxylic acid chlorides followed by t

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Selective production of bio-based: Para -xylene over an FeOx -modified Pd/Al2O3catalyst

para-Xylene (PX) is a basic building block of polyethylene terephthalate, which is currently produced from petroleum resources. Developing a renewable route to PX is highly desirable to address both economic and environmental concerns. Several attempts used noble metal catalysts, e.g. Pd/Al2O3, to synthesize PX from biomass-derived 4-methyl-3-cyclohexene-1-carboxaldehyde (4-MCHCA), but suffered from a severe decarbonylation reaction, resulting in toluene as the main product. In this paper, we report an FeOx modification strategy to suppress the decarbonylation reaction on a Pd/Al2O3 catalyst, leading to a drastic shift in selectivity towards PX with a yield up to 81percent via a cascade dehydroaromatization-hydrodeoxygenation (DHA-HDO) pathway. Characterization and control experiments revealed that the electron density of Pd sites decreased in an FeOx-modified Pd/Al2O3 catalyst compared to Pd/Al2O3, thus tuning the preferential adsorption mode of the substrate from η2-(C,O), the key transition state of the decarbonylation reaction, to the η1-(O) mode that favors the hydrodeoxygenation process. Notably, this designed catalyst is highly stable and is readily applicable in the selective synthesis of a broad range of desired aromatic chemicals via the same DHA-HDO pathway from cyclohex-3-enecarbaldehyde derivatives. Overall, this work develops a controllable catalyst modification strategy that tailors an efficient catalyst for petroleum-independent bio-PX synthesis.

TRNA SYNTHETASE INHIBITORS

Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.

Synthesis of Main-Chain Ionic Polymers of Chiral Imidazolidinone Organocatalysts and Their Application to Asymmetric Diels–Alder Reactions

Main-chain ionic polymers incorporating chiral imidazolidinone moieties in the polymer main chain were successfully synthesized by the polyaddition reaction of a chiral imidazolidinone dimer with a disulfonic acid. The organocatalytic activities of these polymers were investigated in the asymmetric Diels–Alder reaction between trans-cinnamaldehyde and 1,3-cyclopentadiene. The catalytic performance of the polymers was found to be sensitive to the chemical structure of the disulfonate units and the imidazolidinone dimer. With the use of these heterogeneous polymeric chiral organocatalysts, enantioselectivities of up to 99% for the endo isomer were obtained. This result was higher than those obtained with corresponding monomeric and dimeric counterparts in a homogeneous solution. The polymeric chiral organocatalyst was recovered and reused several times, maintaining its high enantioselectivity. (Figure presented.).

Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions

Tungsten carbide was employed as the catalyst in an atom-economic and renewable synthesis of para-xylene with excellent selectivity and yield from 4-methyl-3-cyclohexene-1-carbonylaldehyde (4-MCHCA). This intermediate is the product of the Diels–Alder reaction between the two readily available bio-based building blocks acrolein and isoprene. Our results suggest that 4-MCHCA undergoes a novel dehydroaromatization–hydrodeoxygenation cascade process by intramolecular hydrogen transfer that does not involve an external hydrogen source, and that the hydrodeoxygenation occurs through the direct dissociation of the C=O bond on the W2C surface. Notably, this process is readily applicable to the synthesis of various (multi)methylated arenes from bio-based building blocks, thus potentially providing a petroleum-independent solution to valuable aromatic compounds.

Methods for preparing benzene-ring-containing compounds from pinacol

The invention relates to methods for preparing durene, 1,2,3-trimethylbenzene, o-xylene, pyromellitic acid and trimellitic acid from pinacol. Durene, 1,2,3-trimethylbenzene and o-xylene are prepared through three steps of reaction, and pyromellitic acid and trimellitic acid are prepared through four steps of reaction. A catalytic system used in the invention is green and environment-friendly, andcan be recycled. The raw materials of method, i.e., pinacol, crotonaldehyde, acrolein and crotonate can all be derived from biomass, and are cheap and easily available. All the reaction processes aresimple and are high in activity and selectivity in the dehydration of pinacol and the dehydrogenation, decarbonylation and oxidation of D-A products. The invention provides novel methods for preparingfine chemicals including durene, 1,2,3-trimethylbenzene, o-xylene, pyromellitic acid and trimellitic acid from lignocellulose-based platform chemicals.