31089-24-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3988, 1989 DOI: 10.1021/jo00277a047

InChI:InChI=1/C9H14O/c1-6(2)9-7(3)4-5-8(9)10/h6H,4-5H2,1-3H3

Upstream product

• 31089-10-8 2-isopropylidene-4-methyl-cyclopentanone 
• 10200-21-2 γ-methyl-γ-isobutyl-γ-butyrolactone 
• 53626-90-7 7-methyl-octane-2,5-dione 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 54298-97-4 2-methyloct-7-en-4-one 
• 503-74-2 3-methylbutyric acid 
• 90673-64-6 2-methyl-1-(5-methylfuran-2-yl)propan-1-one 
• 70390-90-8 2-methyl-5-(2-methylpropyl)furan 

Downstream Products

• 10200-23-4 (4SR,5SR)-4-methyl-5-prop-2'-yl-δ-valerolactone 

Relevant academic research and scientific papers

Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process

(Chemical Equation Presented) We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation.

The Cyclisation of Geraniol in Superacids

The cyclisation of geraniol (1) in FSO3H-SO2 at -78 deg C to yield the iridoid ether 3β,4α,6aα-trimethyl-cis-perhydrocyclopentafuran was investigated.Decomposition of the ether in FSO3H at room temperature gave the 2-isopropyl-1,3-dimethylcyclopentenium ion, whose structure was confirmed independently.Synthesis of geraniol labelled with deuterium on the gem-dimethyl group and on the single methyl group established the positions of these mehtyls in the iridoid ether.Synthesis of 2-(1-hydroxy-2,2-dimethylcyclopentyl)propan-1-ol established that the ion derived from it did not lie on the reaction pathway.

A Convenient Preparative Method of Jasmone and its Related Compounds

The reaction of (Z)-hept-4-enoic acid (1) with vinylmagnesium bromide gave (Z)-undeca-1,8-dien-5-one (2).The oxidation of the terminal vinylic group of (2) affords (Z)-undec-8-ene-2,5-dione (3).Jasmone (4) was obtained by the usual alkali cyclization of (3).A variety of alkylcyclopentenones were prepared by the same method.