17351-10-9

Upstream product

• 101046-10-0 (3aS,7aR)-1,1-Dimethyl-3-oxo-hexahydro-isobenzofuran-3a-carbonitrile 
• 101046-11-1 (3aR,7aS)-1,1-Dimethyl-3-oxo-hexahydro-isobenzofuran-3a-carboxylic acid methyl ester 
• 101046-11-1 (3aR,7aR)-1,1-Dimethyl-3-oxo-hexahydro-isobenzofuran-3a-carboxylic acid methyl ester 
• 74-88-4 methyl iodide 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 67-63-0 isopropyl alcohol 
• 101045-99-2 2-Cyano-8-methyl-non-7-enoic acid ethyl ester 
• 917-64-6 methyl magnesium iodide 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 101046-02-0 2-(6-Methyl-hept-5-enyl)-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Fungistatic activity of bicyclo[4.3.0]-γ-lactones

Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo[4.3.0]nonan-2-one (3c), IC50 = 30.1 μg/mL (0.10 μM/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2- one (3b), IC50 = 72.2 μg/mL (0.47 μM/mL), toward F. oxysporum AM 13.

A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media

α,β-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1,3-dioxolane as radical precursor, monoprotected 1,4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexencarboxyaldehyde in a moderate yield, and in a low yield from β-aryl-α,β-unsaturated aldehydes. With 2-alkyl-1,3-dioxolanes, monoprotected 1,4-ketoaldehydes were analogously prepared. By using methanol, ethanol and isopropanol as radical precursors γ-lactols were likewise obtained from the above aliphatic aldehydes. These single-step syntheses compared favorably with multi-step approaches previously proposed for some of these compounds. The lactols were conveniently oxidized to the corresponding γ-lactones. An alternative to the photosensitisation in organic medium was the use of mixed aqueous-organic solvent and a hydrosoluble photosensitiser (benzophenone disodium disulfonate was prepared for this purpose and successfully used), which allowed a more convenient work up.

INTRAMOLECULAR LACTONE ANNULATION OF ACTIVATED ACIDS WITH Mn(III)

Intramolecular lactone annulation of activated carboxylic acids onto olefins by manganese(III) acetate yields bicyclo and lactones.