18594-05-3

Usage

Uses

Used in Pharmaceutical Industry:
4'-Cyclohexylacetophenone is used as an antimycobacterial agent for its ability to combat mycobacterial infections, such as tuberculosis. Its chemical properties make it a promising candidate for the development of new drugs to treat these types of infections.
Used in Chemical Research:
4'-Cyclohexylacetophenone is used as a subject of study in chemical research to understand its spectral properties and potential applications in the synthesis of various compounds. The preparation and study of its tricarbonylchromium complexes have provided valuable insights into its chemical behavior and potential uses.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1105, 1946 DOI: 10.1021/ja01210a059

InChI:InChI=1/C14H18O/c1-11(15)12-7-9-14(10-8-12)13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3

Upstream product

• 622-45-7 cyclohexyl acetate 
• 71-43-2 benzene 
• 827-52-1 1-phenyl-1-cyclohexane 
• 108-24-7 acetic anhydride 
• 110-82-7 cyclohexane 
• 98-86-2 acetophenone 
• 72825-30-0 4'-cyclohexyl-2-chloroacetophenone 
• 108-85-0 1-bromocyclohexane 
• 13329-40-3 4-Iodoacetophenone 
• 108-93-0 cyclohexanol 
• 4441-56-9 cyclohexylboronic acid 
• 99-90-1 para-bromoacetophenone 
• 109613-00-5 4-acetophenyl triflate 
• 108-91-8 cyclohexylamine 

Downstream Products

• 40231-37-6 1-(4-cyclohexyl-phenyl)-1-phenyl-ethene 
• 20029-52-1 4-cyclohexylbenzoic acid 
• 29030-52-2 1-(4'-Cyclohexyl-phenyl)-1-hydroxy-ethane 
• 333969-81-6 2-(4-cyclohexylphenyl)quinoline-4-carboxylic acid 
• 59721-36-7 4-(p-Cyclohexylphenyl)-3-penten-2-on 
• 119549-98-3 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-cyclohexyl-phenyl)propan-1-one 
• 82760-72-3 methyl 4-(4-cyclohexylphenyl)-2,4-dioxo-1-butanoate 
• 70262-86-1 (4-Cyclohexyl-phenyl)-acetic acid methyl ester 
• 74067-99-5 ossima del 4-cicloesilacetofenone 
• 99433-28-0 2-bromo-1-(4-cyclohexylphenyl)ethanone 
• 110510-77-5 C₁₄H₁₅⁽²⁾H₃O 
• 343778-61-0 1-Bicyclohexyl-1-en-4-yl-ethanol 
• 219298-43-8 4'-cyclohexyl-3,5-dimethoxychalcone 

Relevant academic research and scientific papers

Study on the design, synthesis and structure-activity relationships of new thiosemicarbazone compounds as tyrosinase inhibitors

52 Structure-based thiosemicarbazone compounds bearing various substituted-lipophilic part, including substituted-benzaldehyde, substituted-phenylalkan-1-one and their biphenyl-type thiosemicarbazone analogs, were designed, synthesized and evaluated as new tyrosinase inhibitors. The results demonstrated that 22 compounds have potent inhibitory activities against tyrosinase with the IC50 value of lower than 1.0 μM. On the basis of the obtained experimental data, the structure-activity relationships (SARs) were rationally derived. Besides, the inhibition mechanism and the inhibitory kinetics of selected compounds 3d and 6e were investigated, revealing that such type of compounds were belonged to the reversible and competitive tyrosinase inhibitors. To verify the safety of these developed thiosemicarbazone compounds, four randomly selected compounds 3d, 4e, 6a and 9a were also tested in 293T cell line for the evaluation of the cytotoxicity. Interestingly, all these compounds almost did not perform any toxicity to 293T cells even at a high concentration of 1000 μmol/L. Taken together, these results suggested that such compounds could serve as the highly efficient and more safe candidates for the treatment of tyrosinase-related disorders.

Alkyl-GeMe3: Neutral Metalloid Radical Precursors upon Visible-Light Photocatalysis

Single-electron transfer (SET) oxidation of ionic hypervalent complexes, in particular alkyltrifluoroborates (Alkyl-BF3?) and alkylbis(catecholato)silicates (Alkyl-Si(cat)2?), have contributed substantially to alkyl radical generation compared to alkali or alkaline earth organometallics because of their excellent activity–stability balance. Herein, another proposal is reported by using neutral metalloid compounds, Alkyl-GeMe3, as radical precursors. Alkyl-GeMe3 shows comparable activity to that of Alkyl-BF3? and Alkyl-Si(cat)2? in radical addition reactions. Moreover, Alkyl-GeMe3 is the first successful group 14 tetraalkyl nucleophile in nickel-catalyzed cross-coupling. Meanwhile, the neutral nature of these organogermanes offset the limitation of ionic precursors in purification and derivatization. A preliminary mechanism study suggests that an alkyl radical is generated from a tetraalkylgermane radical cation with the assistance of a nucleophile, which may also result in the development of more non-ionic alkyl radical precursors with a metalloid center.

Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.

Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in waterviasynergistic nickel and copper catalysis

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developedvianickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale.

Nickel-Catalyzed, para-Selective, Radical-Based Alkylation of Aromatic Ketones

A direct, para-selective, radical-based alkylation of aromatic ketones with alkanes has been developed using a nickel catalyst with oxamide as the ligand. Acetophenones bearing electron-withdrawing substituents were functionalized directly with simple alkanes with high para-selectivity while acetophenones with electron-donating groups were mainly para-functionalized. A mechanistic study indicated that C-H bond activation of the aromatic ring may be the rate-determining step of the reaction.

Preparation method of siponimod intermediate

The invention relates to a preparation method of a siponimod intermediate, belonging to the field of medicinal chemistry. The preparation method comprises the following steps: with cyclohexylbenzene as a starting material, carrying out reactions such as Friedel-Crafts acylation, bromination, oxidation, esterification, trifluoromethylation and hydrolysis to obtain 4-cyclohexyl-3-trifluoromethyl benzoic acid. Such a technical scheme provided by the invention is simple and convenient to operate, easy to implement, mild in reaction conditions, high in yield, high in purity, low in cost and suitable for industrial production.

A Practical Method for Continuous Production of sp3-Rich Compounds from (Hetero)Aryl Halides and Redox-Active Esters

A practically useful coupling reaction between aromatic halides and redox-active esters was realized by nickel catalysis through the use of a packed zinc bed column in continuous flow. Multiple reuse of the column showed a negligible decrease in efficiency, affording high space/time yields. A wide range of substrates, including a number of heteroaryl halides and polyfunctional materials were coupled in generally good yields. Longer-time and larger-scale experiments further demonstrates the robustness of the system.

Nickel-catalyzed C-N bond activation: Activated primary amines as alkylating reagents in reductive cross-coupling

Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media

An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.