22418-73-1

Usage

InChI:InChI=1/C8H15NO/c1-7(2)5-4-6-8(3)9-10/h5,10H,4,6H2,1-3H3

Upstream product

• 106023-79-4 6-Methyl-hept-5-en-2-one O-allyl-oxime 
• 110-93-0 6-Methyl-hept-5-en-2-on 

Downstream Products

• 22462-79-9 6-methylhept-5-en-2-amine 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 69169-53-5 C₁₅H₂₂N₂O₂ 
• 124920-20-3 2-Isopropyl-5-methyl-1-(toluene-4-sulfonyl)-pyrrolidine 
• 913539-58-9 N-(1,5-dimethylhex-4-en-1-yl)(4-methylphenyl)sulfonamide 

Relevant academic research and scientific papers

Piperidines from acid-catalysed cyclisations: Pitfalls, solutions and a new ring contraction to pyrrolidines

The success of acid-catalysed cyclisations of alka-4-enylamine derivatives to piperidines depends very much on the nature of the amine protecting group: while carbamates and related amides can usually be readily and cleanly transformed, the corresponding sulfonamides react further by ring contraction leading to pyrrolidines, especially when such substrates are sterically crowded.

Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles

Symmetrical and unsymmetrical dioxime oxalates were prepared by treatment of oximes with oxalyl chloride. UV photolysis of these precursors was found to be an atom-efficient way of generating iminyl radicals. The process was most efficient for dioxime oxalates having aryl substituents attached to their C{double bond, long}N bonds. The method was useful for EPR spectroscopic study of iminyl and iminoxyl radicals. Photolyses in toluene solution, of dioxime oxalates containing alkenyl acceptor groups, yielded unsaturated iminyl radicals that ring closed to afford 3,4-dihydro-2H-pyrroles in good yields. Dioxime oxalates with biphenyl substituents also released iminyl radicals that ring closed onto the aromatic acceptor groups and, in acetonitrile solution, this approach provided a useful and atom-efficient method of making substituted phenanthridines.

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.

O-ALLYL ETHER AS A NEW PROTECTIVE GROUP FOR OXIMES AND ITS PALLADIUM-CATALYZED DEPROTECTION.

Oximes are protected by O-allyl ether formation, and their palladium-catalyzed deallylation using triethylammonium formate as a reductant proceeds smoothly in boiling ethanol under mild conditions offering a good protective method for oximes.