5739-17-3

Usage

InChI:InChI=1/C11H18O/c1-3-4-5-6-10-7-8-11(12)9(10)2/h3-8H2,1-2H3

Upstream product

• 70219-54-4 4-methyl-2-decyne-1,4-diol 
• 74676-73-6 (2,2-Dichloro-3-hexyl-3-methyl-cyclopropyl)-methanol 
• 111-13-7 hexyl-methyl-ketone 
• 3525-31-3 n-pentyl lithium 
• 17024-44-1 2,3-epoxy-3-methylcyclopentanone 
• 74-85-1 ethene 
• 67220-89-7 3,3-Dichloro-4-methyl-dec-1-en-4-ol 

Relevant academic research and scientific papers

Unexpected reaction of 2,3-epoxy sulfonates: Novel formation of two enones with reversed substituents at α- and β-positions from the single isomer

The 2,3-epoxy sulfonates gave two types of enones with reversed substituents at the α- and β-positions under neat and weakly acidic conditions. The reaction mechanism is also discussed.

The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol

The Lewis acid treatment of 2,3-epoxysulfonates with 2,3-dialkyl substituents or 2-alkyl-3-aryl substituents produced the rearrangement products via C3-cleavage of the oxirane ring in high yields. On the other hand, 2-aryl-3-alkyl-2,3-epoxysulfonates produced the products via C2-cleavage of the oxirane ring. The sulfonyloxy groups of the α-sulfonyloxy ketones, having a chiral benzylic quaternary carbon center obtained by the rearrangement of 2-alkyl-3-aryl-2,3-epoxysulfonates, were reductively eliminated to give the ketones with a chiral benzylic quaternary carbon center. The method was applied to the formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol.

Reaction of cyclic α-hydroxy epoxides with a strong base: A new 1,2-rearrangement, evidence for a carbenoid pathway

Several substituted five- and six-membered cyclic α,β-unsaturated ketones are readily available by treatment of the corresponding α-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.

Syntheses of Jasmone, Jasmonic Acid and some Analogues from Alkyne-cobalt Complexes via the Khand Reaction.

The Khand reactions of the hexacarbonyldicobalt complexes of 2-octyne and of Z-oct-5-en-2-yne with ethylene lead directly to jasmone and dihydrojasmone. 2-Pentyl- and Z-2-pentenylcyclopent-2-en-1-one, known intermediates in the synthesis of jasmonic and dihydrojasmonic acid or their esters, have been obtained similarly from 1-heptyne and hept-4-en-1-yne respectively.These and related cyclopentenones have been converted into new analogues of methyl jasmonate, of interest as potential plant growth regulators.

Regio- and Stereoselective Cyclopentannulation with Ketones and Propargyl Alcohol Derivatives. Synthesis of dl-Nootkatone and dl-Muscopyridine

A highly regio- and stereoselective five-membered ring annulation involving the acid-treatment of propargyl alcohol dianion adducts of ketones is described.The propargyl alcohol adduct of 2-octanone was converted into 2-methyl-3-pentyl-2-cyclopentenone by treatment with sulfuric acid-methanol (1:1) at 0 deg C.As the major product, 1-methylbicyclodec-6-en-8-one was produced from 2-methylcycloheptanone.Remarkable regioselective cyclopentannulation was observed in 2-methylcyclohexanone and 2,3-dimethylcyclohexanone wherein 1-methyl- and trans-1,2-dimethyl-substituted bicyclonon-5-en-7-one (BNO) are produced, respectively.With 3-butyn-2-ol, 2-methylcyclohexanone was converted into the cis-1,9-dimethyl-substituted BNO. 4-Isopropyl-2-methylcyclohexanone was transformed into an 83-85:17-15 mixture of c-3-isopropyl-r-1,c-9-dimethyl-BNO and its 3-epimer.These results are explained in terms of the conrotatory ring-closure of thermodynamically most favorable hydroxypentadienyl cation intermediates. 3-Methoxycarbonyl-cis-1,9-dimethyl-BNO produced from 4-methoxycarbonyl-2-methylcyclohexanone and 3-butyn-2-ol was successfully transformed into dl-nootkatone by converting the methoxycarbonyl group into isopropenyl of correct stereochemistry followed by ring enlargement.Cyclopentannulation using propargyl alcohol dianion adducts of 2-cycloalkenones is discussed.Annulation takes place regioselectively to give conjugated dienones, e.g., (E)-bicyclopentadeca-1(12),2-dien-13-one from 2-cyclododecenone.This product is led to dl-muscopyridine by conjugate 1,6-addition of methyl group followed by ring expansion and finally by aromatization with hydroxylamine hydrochloride.

Cyclopentenone Synthesis from 1,1-Dichloroallyllithium-Ketone Adducts as Well as from Dichlorocarbene-Allyl Alcohol Adducts

Treatment of (3,3-dialkyl-2,2-dichlorocyclopropyl)methanols with hydrobromic acid gives 2-cyclopentenones through postulated intermediates, 3-chlorocyclopentadienyl cations.Another method which should give the same cationic intermediates involves trifluoroacetic acid catalyzed reaction of 3,3-dichloro-1-alken-4-ols.This is found to be particularly useful for cyclopentenone annulation.