7207-49-0

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

InChI:InChI=1/C8H17NO/c1-3-4-5-6-7-8(2)9-10/h10H,3-7H2,1-2H3

Upstream product

• 4609-91-0 2-nitrooctane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 16630-91-4 2-methylheptanal 
• 4128-31-8 rac-octan-2-ol 
• 111-13-7 hexyl-methyl-ketone 
• 629-05-0 n-octyne 
• 44855-57-4 rac-2-aminooctane 
• 140387-66-2 2-(2-tetrahydropyranyloxy)octane 
• 18023-52-4 trimethyl-(1-methyl-heptyloxy)-silane 
• 93548-38-0 (E)-2-nitro-oct-2-ene 

Downstream Products

• 53502-26-4 C₁₆H₂₁Cl₂NO₃ 
• 2074-06-8 2-octanone 2,4-dinitrophenylhydrazone 
• 34566-04-6 (S)-octan-2-amine 
• 693-16-3 (R)-2-octylamine 
• 18320-91-7 2-methyl-3-pentyl-1H-pyrrole 
• 64222-37-3 2-methyl-3-pentyl-1-vinyl-pyrrole 
• 97421-51-7 Octan-2-one O-{2-[1-methyl-hept-(E)-ylideneaminooxy]-ethyl}-oxime 
• 111-13-7 hexyl-methyl-ketone 
• 3400-24-6 N-methylheptanamide 
• 753386-51-5 3-amino-octan-2-one 
• 132329-18-1 4-Octyloxy-benzoic acid 3-hydroxy-4-{[(E)-1-methyl-heptylimino]-methyl}-phenyl ester 
• 65500-65-4 (1-methyl-heptyl)-hydrazine 
• 326812-18-4 N-diphenylphosphinyl-1,1-methylhexyl imine 
• 7501-79-3 N-hexylacetamide 

Relevant academic research and scientific papers

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Iron-Catalyzed C-N Bond Formation via the Beckmann Rearrangement

A simple, iron-based catalytic system allows for facile Beckmann rearrangement of various oximes. The mild conditions avoid the use of harsh or expensive acids, and the reactions do not require an inert atmosphere. Additionally, a range of amides can be accessed through this transformation.

Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid

Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.

Selenium-catalyzed deoxygenative reduction of aliphatic nitro compounds with carbon monoxide

A reduction method of aliphatic nitro compounds to oximes using carbon monoxide was developed. When aliphatic nitro compounds were treated with carbon monoxide in the presence of a selenium catalyst, the corresponding oximes were formed in moderate to good yields.

The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction

The bioreduction of aliphatic sec-nitro compounds catalyzed by purified flavoproteins from the old-yellow-enzyme family unexpectedly furnished the corresponding carbonyl compounds instead of the expected amines and thus represents a biocatalytic equivalent to the Nef-reaction. The pathway was shown to proceed via initial reduction of the nitro-group to yield the nitroso-derivative, which spontaneously tautomerized to yield the more stable oxime, which was enzymatically reduced in a second step to furnish a hydrolytically unstable imine-species, which spontaneously hydrolyzed to finally give a carbonyl compound and ammonia.

Intermolecular Cope-type hydroamination of alkenes and alkynes using hydroxylamines

The development of the Cope-type hydroamination as a method for the metal- and acid-free intermolecular hydroamination of hydroxylamines with alkenes and alkynes is described. Aqueous hydroxylamine reacts efficiently with alkynes in a Markovnikov fashion to give oximes and with strained alkenes to give N-alkylhydroxylamines, while unstrained alkenes are more challenging. N-Alkylhydroxy-lamines also display similar reactivity with strained alkenes and give modest to good yields with vinylarenes. Electron-rich vinylarenes lead to branched products while electron-deficient vinylarenes give linear products. A beneficial additive effect is observed with sodium cyanoborohydride, the extent of which is dependent on the structure of the hydroxylamine. The reaction conditions are found to be compatible with common protecting groups, free OH and NH bonds, as well as bromoarenes. Both experimental and theoretical results suggest the proton transfer step of the N-oxide intermediate is of vital importance in the intermolecular reactions of alkenes. Details are disclosed concerning optimization, reaction scope, limitations, and theoretical analysis by DFT, which includes a detailed molecular orbital description for the concerted hydroamination process and an exhaustive set of calculated potential energy surfaces for the reactions of various alkenes, alkynes, and hydroxylamines.

Intermolecular cope-type hydroamination of alkenes and alkynes

(Chemical Equation Presented) Keep it simple! Intermolecular hydroamination can be achieved simply upon heating alkynes and alkenes with aqueous hydroxylamine. Alkynes react to afford oximes in good to excellent yields, and the formation of Markovnikov products is favored. A mechanism involving Cope-type hydroamination followed by bimolecular proton transfer is suggested and supported by DFT studies.

Transfer hydrogenation process

A catalytic transfer hydrogenation process is provided. The process can be employed to transfer hydrogenate N-substituted imines and iminium salts, which are preferably prochiral. The catalyst employed in the process is preferably a metal complex with one hydrocarbyl or cyclopentadienyl ligand and which is also coordinated to defined bidentate ligands. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centres. The hydrogen donor is advantageously a mixture of triethylamine and formic acid. A process for the production of primary and secondary amines using the catalytic transfer hydrogenation of the N-substituted imines and iminium salts is also provided.

A convenient one-pot method of converting alcohols into oximes

The one-pot conversion of primary and secondary alcohols into oximes is reported using chromium trioxide supported on alumina and hydroxylamine hydrochloride under solvent free condition. This oxidation-oxime formation reaction has been applied to a range of aliphatic and benzylic alcohols.