56606-79-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7589, 1995 DOI: 10.1021/jo00128a035Tetrahedron Letters, 22, p. 4889, 1981 DOI: 10.1016/S0040-4039(01)92373-1

Upstream product

• 101999-59-1 10-Iodo-dec-1-en-3-one 
• 2384-70-5 dec-2-yne 
• 872-05-9 1-Decene 

Downstream Products

• 83467-48-5 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 1437682-55-7 benzyl (2S,2αS,5R)-2-(1-hydroxybutyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-59-1 benzyl (2S,2αR,5R)-2-(1-hydroxybutyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-82-0 benzyl (2S,2αS,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-78-4 benzyl (2S,2αS,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 63950-16-3 cis-6-methyl-2-undecanylpiperidine 
• 28720-60-7 solenopsin A 

Relevant academic research and scientific papers

Solvent-Free Aerobic Epoxidation of Dec-1-ene Using Gold/Graphite as a Catalyst

The oxidation of dec-1-ene has been investigated using gold nanoparticles supported on graphite in the presence of a radical initiator (α,α-azobisisobutyronitrile) using oxygen from air as oxidant. We have investigated the influence of the reaction temperature (70-100 °C), catalyst mass and reaction time on the epoxide yield. In the absence of a radical initiator the reaction does not proceed, although auto-oxidation can occur at higher temperatures in the range studied. However, in the presence of an initiator, selective oxidation occurs and the initiator propagates the reaction through the formation of a peroxy-radical at the allylic C3 position. Graphite enhances the formation of the allylic products dec-1-en-3-ol, dec-1-en-3-one, and dec-2-en-1-ol; however, the addition of gold nanoparticles to the graphite, enhances formation of 1,2-epoxydecane. It is suggested that gold suppresses the formation of allylic products via a Russell termination. Graphical Abstract: [Figure not available: see fulltext.]

Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: Propargyl moieties as masked α,β-unsaturated carbonyls

Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N3, OTBS, and N-Boc are tolerated. This reaction allows α,β-unsaturated carbonyls to be masked as propargyl moieties, thus offering a practical solution to compatibility issues with these functional groups likely encountered in syntheses of complex structures.

1-Alkenylcycloalkoxy Radical Chemistry. A Two-Carbon Ring Expansion Methodology

The exploitation of alkoxy radicals derived from 1-ethenylcycloalkanols for use in a two-carbon ring expansion protocol was proposed.Direct one-pot alkoxy radical-mediated fragmentation-cyclization was not feasible since the reactive intermediate was quenched by iodine in the reaction mixture.However, via the use of iodo epoxides 3, the tandem fragmentation-cyclization sequence could be accomplished.This afforded ring-expanded products via an endo mode of cyclization, although in one example product from an exo mode of cyclization was also isolated.This methodologywas shown to be valid for large ring compounds as well.The intermediary of iodo epoxides 3 also afforded improved yields as compared to the direct cyclization of iodo enones 4.These results are the first examples of radical cyclization to medium-sized carbocycles.