50405-95-3

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InChI:InChI=1/C9H12O2/c1-6(2)8-4-7(3)5-9(10)11-8/h4-6H,1-3H3

Upstream product

• 97309-29-0 trans-5-Hydroxy-4-methyl-6-(1-methylethyl)-5,6-dihydro-2H-pyran-2-on 
• 68077-47-4 (E)-3,6-Dimethyl-5-oxo-hept-2-enoic acid methyl ester 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 79-30-1 isobutyryl chloride 
• 97309-65-4 (Z)-4,5-Epoxy-3,6-dimethyl-2-heptansaeure-ethylester 
• 18150-99-7 2-methyl-3,4-epoxy-5-hexanone 
• 541-47-9 3-Methylbutenoic acid 
• 924-50-5 Methyl 3,3-dimethylacrylate 

Relevant academic research and scientific papers

Formal ring-opening/cross-coupling reactions of 2-pyrones: Iron-catalyzed entry into stereodefined dienyl carboxylates

Open access: Despite the exceptional level of sophistication in cross-coupling chemistry, reactions of substrates that incorporate the leaving group as an integral part into a heterocyclic scaffold are scarce. The title reaction outlines the utility of this reaction format (see scheme; acac=acetylacetonate), provides a convenient entry into stereodefined diene carboxylates, and adds a new chapter to the field of iron catalysis. Copyright

Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones

A number of 4-methyl-6-alkyl-α-pyrones were synthesized and characterized on the basis of 1H NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-α-pyrone, 4-methyl-6-pentyl-α-pyrone, 4-methyl-6-hexyl-α-pyrone, and 4-methyl-6-heptyl-α-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 μg/mL. 4-Methyl-6-hexyl-α- pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-α-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.

Formation and Reactivity of Hydroxy-substituted γ- and δ-Lactones

Hydrolysis of the esters (Z)-6-8 with H2SO4 in acetone leads to a mixture of γ- (17-19) and δ-Lactones (13-15) in various ratios.From (Z)-9 the rearrangement product 20 is obtained.By reaction of (Z)-6-9 with Et2O-BF3 the δ-lactones 13-16 are formed only.The saturated esters 10-12 hydrolyze to give a γ/δ-lactone mixture 24-26/21-23.Changing to BF3, favors the rearrangement 10 -> 30. - The δ-lactones 13-16 are not dehydrated with POCl3 in pyridine but chlorinated to afford 31-34.On heating in pyridine 33 and 34 are dehydrochlorinated to give the α-pyrones 38 and 39.Dechlorination with zinc in acetic acid leads to β,γ-unsaturated δ-lactones (31,35 -> 44; 32 -> 45; 33 -> 46).The mixture of saturated γ/δ-lactones 21b/24a/24b yields with POCl3 the elimination products 50 and 51, while a 23/26a/26b mixture furnishes the unsaturated γ-lactones 53a, b, and 54 as well as the chlorinated δ-lactones 55.Hydrogenation (44 -> 56; 45 -> 57; 46 -> 58; 51-> 59; 53/54 -> 60) gives the saturated parent compounds.