67663-01-8

Usage

Chemical Properties

(+/–)3-Methyl-gamma-decalactone has a floral aroma.

InChI:InChI=1/C11H20O2/c1-3-4-5-6-7-10-9(2)8-11(12)13-10/h9-10H,3-8H2,1-2H3

Upstream product

• 120132-11-8 5-Hexyl-4-methyl-tetrahydro-furan-2-ol 
• 111-71-7 heptanal 
• 84510-39-4 (3RS,4SR,1Z)-4-hydroxy-1-methoxymethoxy-3-methyldec-1-ene 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 24404-67-9 (Z)-3-methyldec-4-enoic acid 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 109066-11-7 3-methyltetrahydrofuran-2-ol 
• 24404-72-6 (Z)-3-methyldec-4-en-1-ol 
• 120132-11-8 (4R,5S)-5-Hexyl-4-methyl-tetrahydro-furan-2-ol 

Relevant academic research and scientific papers

An expedient synthesis of olfactory lactones by intramolecular hydroacylalkoxylation reactions

A series of 4,5-disubstituted γ-lactones, including whisky and cognac lactones, was synthesised in four steps from a readily available chiral precursor. By using an intramolecular hydroacylalkoxylation reaction in the final step, a correlation between the (E)/(Z) configuration of the precursor and the product distribution has been established, for the first time, in this type of cyclisation reactions. Copyright

Solid-support synthesis of 1,2-diols and γ-lactones through addition of α-(benzoyloxy)crotylindium reagents to aldehydes

A procedure for the solid phase synthesis of 1,2-diols and γ-lactones from α-(hydroxy)crotylstannane has been developed through transmetalation with InBr3. A variety of 1,2-diols and γ-lactones were synthesized in satisfactory yields and, in some cases, with excellent diastereoselectivity. The products are formed free of tin contamination.

Stereoselective Thermal Reactions between (E)-1-Alkoxymethoxybut-2-enyl(tributyl)stannanes and Aldehydes

(E)-1-Methoxymethoxybut-2-enyl(tributyl)stannane (6), readily available by the addition of tributylstannyl-lithium to crotonaldehyde and alkylation of the adduct using chloromethyl methyl ether, reacts on heating with aldehydes to give anti-4-hydroxy-3-methyl-cis-1,2-enol ethers.These on hydrolysis and oxidation provide trans-4,5-disubstituted butyrolactones.

On The Use of E-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-Selective, Homo-enolate Equivalent

(E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyl-lithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4-hydroxy-3-methyl-cis-1,2-enol ethers, hydrolysis and oxidation of which provides a stereoselective route to trans-4,5-disubstituted butyrolactones.