501-23-5

Upstream product

• 67093-60-1 (+/-)-5-hydroxy-dec-2c-enoic acid methyl ester 
• 87921-59-3 (Z)-1-bromo-1-nonen-4-ol 
• 74986-40-6 trans-2-methoxy-6-pentyl-5,6-dihydro-2H-pyran 
• 135294-89-2 tert-butyl (Z)-5-hydroxy-2-decenoate 
• 36555-25-6 (4S,6R)-4-Hydroxy-6-pentyl-tetrahydro-pyran-2-one 
• 100591-72-8 3-Benzenesulfinyl-6-pentyl-tetrahydro-pyran-2-one 
• 130286-51-0 2-pentyl-3,4-dihydro-2H-pyran 
• 117996-95-9 (+/-)-3,5-dihydroxydecanenitrile 
• 705-86-2 (+/-)-δ-decanolactone 
• 592-76-7 1-Heptene 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 100591-82-0 1-Phenylsulfanyl-nonan-4-ol 
• 5063-65-0 1,2-epoxyheptane 
• 74986-36-0 trans-2-methoxy-6-(1-hydroxypent-1-yl)-5,6-dihydro-2H-pyran 

Downstream Products

• 705-86-2 (+/-)-δ-decanolactone 
• 51154-96-2 (R)-massoialactone 
• 61248-45-1 (6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one 
• 27593-23-3 6-pentyl-2H-pyran-2-one 

Relevant academic research and scientific papers

Synthesis of the racemate and both enantiomers of massoilactone

A simple and efficient synthesis of (±)-massoilactone (1) as a key substance for the butter and milk flavor was accomplished from n-hexanal in only a few steps. Application of its racemic synthesis enabled natural (R)-(-)-and unnatural (S)-(+)-massoilacto

A VERY SIMPLE SYTHESIS OF NATURAL SATURATED δ-SUBSTITUTED δ-LACTONES. THE PHEROMONE OF Vespa orientalis

Very facile syntheses of racemic massoia lacton and the pheromone of Veapa orientialis have been achieved starting from dehydroacetic acid.

Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones

We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.

PPARS AGONIST ACTIVITY ENHANCING DRUG

According to the present invention, PPARs agonist activity is enhanced in order to improve metabolic syndrome, hyperlipidemia, and diabetes. Provided is a compound having a lactone structure comprising formula (9).

High-Performance Isocyanide Scavengers for Use in Low-Waste Purification of Olefin Metathesis Products

Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removi

2H-pyran-2-ones from trichoderma viride and trichoderma asperellum

Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one, 6-propyl-2H-pyran-2-one, and 6-heptyl-2H-pyran-2-one were found. The alkenyl derivative (E)-6-(hept-1-en-1- yl)-2H-pyran-2-one, previously tentatively identified from a marine Botrytis by MS analysis, was also detected. All alkenyl pyrones were synthesised by using a reported Stille coupling followed by lactonisation, whereas the alkylated pyrones were obtained through a reported synthetic approach by radical bromination of 5-alkylpent-2-en-5-olides and dehydrobromination. Because the yields in both cases were not satisfactory and fell a long way short of the yields reported for similar compounds, all compounds were synthesised again using a gold-catalysed coupling of terminal alkynes with propiolic acid recently developed by Schreiber and co-workers, giving high yields in all cases. A comparison of the synthetic methods is given. Copyright

αβ-Unsaturated δ-valerolactones through RCM-isomerization sequence

αβ-Unsaturated δ-lactones are accessible via a sequential ring-closing metathesis (RCM) double-bond migration reaction starting from butenoates of allyl alcohols. This approach proceeds efficiently with lower catalyst loadings and higher initial substrate concentrations compared to the alternative RCM of acrylates derived from homoallylic alcohols. Georg Thieme Verlag Stuttgart . New York.

Thieme chemistry journal awardees - Where are they now? aldol synthesis by anti-markovnikov hydration of propargyloxy substrates: Feasibility, stereospecifity, and reiterative alkynylation-hydration

Aldol derivatives have been synthesized by redox-neutral catalytic anti-Markovnikov hydration of propargyloxy sub-strates. A reiterative sequence of aldehyde alkynylation and alkyne hydration leads to 1,3-polyol derivatives. Georg Thieme Verlag Stuttgart.

The β-lactone route to β-hydroxy or α,β-unsaturated γ- and δ-lactones. Syntheses of (±)-Massoialactone and (±)-Prelactone B

Aqueous HF promotes the translactonization of silyloxy β-lactones into β-hydroxy or α,β-unsaturated γ- and δ-lactones. The reaction is studied from a theoretical point of view and applied to the racemic synthesis of two natural bioactive δ-lactones.

The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.