4701-98-8

Usage

Uses

Used in Organic Chemistry:
4-(TERT-BUTYL)CYCLOHEXANONE OXIME is used as a reagent for the synthesis of complex organic compounds, leveraging its unique structure and properties to facilitate various chemical reactions.
Used in Coordination Chemistry:
4-(TERT-BUTYL)CYCLOHEXANONE OXIME is used as a ligand in coordination chemistry, where its oxime group can interact with metal ions to form coordination complexes, contributing to the development of new materials and catalysts.
Used in Pharmaceutical Industry:
4-(TERT-BUTYL)CYCLOHEXANONE OXIME is used as an intermediate in the production of pharmaceutical compounds, where its reactivity and structural features can be harnessed to create new drug molecules.
Used in Material Science:
4-(TERT-BUTYL)CYCLOHEXANONE OXIME is used as a building block in the development of new materials, such as polymers and composites, where its chemical properties can be exploited to enhance material performance.

InChI:InChI=1/C10H19NO/c1-10(2,3)8-4-6-9(11-12)7-5-8/h8,12H,4-7H2,1-3H3/b11-9-

Upstream product

• 53255-92-8 4-t-butyl-aci-nitrocyclohexane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 5400-88-4 4-tert-butylcyclohexylamine 
• 34949-01-4 spiro<(4-t-butyl cyclohexane)-1,2'-(4',4'-dimethyl oxazolidine-3' oxyl)> 

Downstream Products

• 2163-34-0 trans-4-t-butylcyclohexylamine 
• 2163-33-9 cis-4-tert-butyl-cyclohexylamine 
• 923947-85-7 4-tert-butyl-1-chloro-1-nitrosocyclohexane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 74002-23-6 4-tert.-Butylcyclohexanimin 
• 75107-61-8 4-tert-butyl-1-chloro-1-nitrocyclohexane 
• 944-19-4 4-tert-butyl-1,1-dimethoxy-cyclohexane 
• 5400-88-4 4-tert-butylcyclohexylamine 
• 135663-21-7 N-(4-(tert-butyl)cyclohex-1-en-1-yl)acetamide 

Relevant academic research and scientific papers

Stereoelectronic effects: Perlin effects in cyclohexane-derived compounds

Stereoelectronic effects in cyclohexanones, methylenecyclohexanes, spiro, and epoxy compounds of cyclohexanes and further derivatives were investigated by measuring 1JC,H coupling constants and by identification of Perlin effects, th

Synthesis of nitrogen-containing monoterpenoids with antibacterial activity

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (?)-menthone oxime (?)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 μg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found–oxime 14 and lactams (?)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 μM, 43.0 μM and 4.6 μM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.

Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates

The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.

Aliphatic C-H Bond Oxidation with Hydrogen Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through Torsional Effects

Substituted N-cyclohexyl amides undergo aliphatic C-H bond oxidation with H2O2 catalyzed by manganese complexes. The reactions are directed by torsional effects leading to site-selective oxidation of cis-1,4-, trans-1,3-, and cis-1,2-cyclohexanediamides. The corresponding diastereoisomers are unreactive under the same conditions. Competitive oxidation of cis-trans mixtures of 4-substituted N-cyclohexylamides leads to quantitative conversion of the cis-isomers, allowing isolation and successive conversion of the trans-isomers into densely functionalized oxidation products with excellent site selectivity and good enantioselectivity.

Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids

Copper-catalyzed directed decarboxylative amination of nonactivated aliphatic carboxylic acids is described. This intramolecular C-N bond formation reaction provides efficient access to the synthesis of pyrrolidine and piperidine derivatives as well as the modification of complex natural products. Moreover, this reaction presents excellent site-selectivity in the C-N bond formation step through the use of directing group. Our work can be considered as a big step toward controllable radical decarboxylative carbon-heteroatom cross-coupling.

Oxidation of primary amines to oximes with molecular oxygen using 1,1-diphenyl-2-picrylhydrazyl and WO3/Al2O3 as catalysts

The oxidative transformation of primary amines to their corresponding oximes proceeds with high efficiency under molecular oxygen diluted with molecular nitrogen (O2/N2 = 7/93 v/v, 5 MPa) in the presence of the catalysts 1,1-diphenyl-2-picrylhydrazyl (DPPH) and tungusten oxide/alumina (WO3/Al2O3). The method is environmentally benign, because the reaction requires only molecular oxygen as the terminal oxidant and gives water as a side product. Various alicyclic amines and aliphatic amines can be converted to their corresponding oximes in excellent yields. It is noteworthy that the oxidative transformation of primary amines proceeds chemoselectively in the presence of other functional groups. The key step of the present oxidation is a fast electron transfer from the primary amine to DPPH followed by proton transfer to give the α-aminoalkyl radical intermediate, which undergoes reaction with molecular oxygen and hydrogen abstraction to give α-aminoalkyl hydroperoxide. Subsequent reaction of the peroxide with WO3/Al2O3 gives oximes. The aerobic oxidation of secondary amines gives the corresponding nitrones. Aerobic oxidative transformation of cyclohexylamines to cyclohexanone oximes is important as a method for industrial production of ε-caprolactam, a raw material for Nylon 6.

Structure correlation study of the beckmann rearrangement: X-ray structural analysis and 13C-13C 1-bond coupling constant study of a range of cyclohexanone oxime derivatives

The X-ray structures of a range of oxime derivatives (1 and 4), of cyclohexanone and 4-tert-butylcyclohexanone, where the electron demand of the oxygenated substituent on the oxime nitrogen (OR) is systematically varied were determined. It was established

A simple synthesis of oximes

The conversion of alicyclic and aliphatic carbonyl compounds as well as aromatic aldehydes into the corresponding oximes (up to quantitative yields) was achieved by simply grinding these reactants, hydroxylamine hydrochloride and sodium hydroxide without solvent. However, this procedure was unsuccessful in the case of aromatic ketones. In this case it was necessary to add silica gel as a catalyst. Springer-Verlag 2006.

Chlorination of oximes with aqueous H2O2/HCl system: Facile synthesis of gem-chloronitroso- and gem-chloronitroalkanes, gem-chloronitroso- and gem-chloronitrocycloalkanes

Chlorination of cyclic and linear ketone oximes with aqueous H 2O2/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine. Georg Thieme Verlag Stuttgart.