32179-89-8

Upstream product

• 583-60-8 2-Methylcyclohexanone 

Downstream Products

• 66417-90-1 3-(4-chloro-phenyl)-7-methyl-4,5,6,7-tetrahydro-benzo[c]isoxazole 
• 145853-38-9 1-chloro-2-methyl-1-nitroso-cyclohexane 
• 86921-61-1 anti-2-methylcyclohexanone oxime mesylate 
• 85028-04-2 C₁₄H₁₉NO₃S 
• 158243-62-0 3,4,5,6-Tetrahydro-3,7-dimethylbenzisoxazole 
• 74221-86-6 2-Methyl-1-nitrocyclohexane 
• 1985-48-4 7-Methylcaprolactam 
• 115668-09-2 cis-N-(Diphenylphosphinyl)-2-methylcyclohexylamine 
• 115668-09-2 trans-N-(Diphenylphosphinyl)-2-methylcyclohexylamine 

Relevant academic research and scientific papers

A Fit-for-Purpose Synthesis of (R)-2-Methylazepane

The preparation of new RSV inhibitors required an efficient synthesis of (R)-2-methylazepane ((R)-1) amenable to large-scale production to support preclinical studies. After consideration of different options, an efficient five-step synthesis relying on t

Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones

Carbon-carbon bond formation is among the most important reactions in organic synthesis. Reconstruction of a carbon-carbon bond through ring-opening C-C bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. However, carbon-carbon bond formation through thermodynamically less favorable C-C bond cleavage has seldom been documented. Herein, we disclose an unusual C-C bond cleavage of cycloketone oxime esters for [4+1] annulation. Under anaerobic copper(I) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical C-C bond cleavage followed by annulation with enaminothiones; that is, α-thioxo ketene N,S-acetals efficiently affording 2-cyanoalkyl-aminothiophene derivatives. Cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective C1 building blocks in the annulation reaction. An iminyl radical mechanism is proposed for the rare C-C bond cleavage/[4+1] annulation cascade.

O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization

[Chemical equation presented] O-Acetyl oxlmes serve as effective directing groups for Pd-catalyzed sp2 and sp3 C-H functionalization reactions. The C-H functionalization products can be subsequently transformed Into ortho- or β-functionalized ketones, alcohols, amines, and heterocycles.

Stereoselective hydride reductions of cyclic N-diphenylphosphinyl imines. Highly diastereoselective syntheses of protected primary amines

Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.