931-22-6

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 3713, 1974 DOI: 10.1021/ja00818a091Tetrahedron Letters, 19, p. 3277, 1978

InChI:InChI=1/C7H10O/c1-5-3-6(2)7(8)4-5/h4,6H,3H2,1-2H3

Upstream product

• 820-54-2 2-methyl-hexa-1,5-dien-3-yne 
• 31059-42-4 dichloro-1,1 dimethyl-2,2 (ethanol-1')-3 cyclopropane 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 
• 74-88-4 methyl iodide 
• 7664-93-9 sulfuric acid 
• 110874-93-6 3,5-dimethyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclopenten-1-one 
• 90533-97-4 3,5-Dimethyl-5-vinyl-Δ²-cyclopentenon-(1) 
• 17219-13-5 1-(2,2-dibromo-3,3-dimethylcyclopropane)ethanol 
• 25346-59-2 4-oxohexanal 
• 53670-70-5 2-acetyl-3-methyl-4-oxopentanoic acid ethyl ester 

Downstream Products

• 1121-33-1 2,4-dimethylcyclopentanone 
• 24156-95-4 3,5,5-trimethylcyclopenten-2-one 
• 483358-73-2 6-ethoxy-2,4-dimethyl-2,3-dihydro-pyridine 
• 104882-72-6 5,6-dihydro-4,6-dimethyl-2(1H)pirydone 

Relevant academic research and scientific papers

Nickel-catalyzed difunctionalization of unactivated alkenes initiated by unstabilized enolates

This report demonstrates the possibility of a nickel-catalyzed difunctionalization of unactivated alkenes initiated by an unstabilized enolate nucleophile. The process tolerates a diverse range of electrophiles, including aryl, heteroaryl, alkenyl, and amino electrophiles. An electron-deficient phosphine ligand and a tetrabutylammonium salt additive were crucial for promoting efficient vicinal difunctionalization.

Manganese(III) acetate based oxidation of substituted α′-position on cyclic α,β-unsaturated ketones

Selective oxidation of the tertiary α′-position on various 2-cyclopentenone, 2-cyclohexenone and aromatic ketone derivatives with manganese(III) acetate is described.

1,4-Ketoaldehydes via Michael-Addition of deprotonated Aldimines to 2-(N-Methylanilino)-acrylonitrile

A new method for the synthesis of the title compounds by a one-pot three component coupling reaction is described.It consists of the reaction of an enolateanion- and an enolcation-equivalent with subsequent alkylation of an acylanion-equivalent.

REACTIVITE DES GEM-DIBROMOCYCLOPROPANES-IV; OUVERTURE ACIDO-CATALYSEE DE GEM-DIHALOGENOCYCLOPROPYLCARBINOLS

By acid catalysis, gem-dihalogenocyclopropylcarbinols are converted into homoallylic α-dihalogenated cations which in general eliminate the hydrogen halide and lead to the 3-halogenopentadienyl cations from which cyclopentenones can be formed by cyclisation.For bicycloheptanes, aromatisation of the 3-halogenopentadienyl cation in benzyl bromide is observed.

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.