6261-18-3

Usage

Uses

Used in Organic Synthesis:
(E)-3-Methyl-2-(pent-2-enyl)cyclopent-2-en-1-one is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of new chemical entities.
Used in Fragrance and Flavor Industry:
In the fragrance and flavor industry, (E)-3-Methyl-2-(pent-2-enyl)cyclopent-2-en-1-one is used as a component to create unique and appealing scents and tastes, capitalizing on its strong, sweet, and fruity odor.
Used in Pharmaceutical Industry:
(E)-3-Methyl-2-(pent-2-enyl)cyclopent-2-en-1-one is used as a compound with potential anti-inflammatory and antioxidant properties, which can be harnessed for the development of new drugs targeting various health conditions.
Used in Cosmetic Industry:
In the cosmetic industry, (E)-3-Methyl-2-(pent-2-enyl)cyclopent-2-en-1-one is used for its beneficial properties, such as anti-inflammatory and antioxidant effects, to create products that can improve skin health and appearance.
Safety Note:
It is important to handle (E)-3-Methyl-2-(pent-2-enyl)cyclopent-2-en-1-one with care, as it may cause irritation to the skin, eyes, and respiratory system if not properly managed.

Upstream product

• 53253-09-1 3-(cis-3-hexen-1-yl)-2-cyclopenten-1-one 
• 4868-21-7 undec-8c-ene-2,5-dione 
• 7051-46-9 undec-8t-ene-2,5-dione 
• 32556-66-4 (4R,5S)-4-Methyl-5-((E)-pent-2-enyl)-cyclopent-2-enone 
• 111-28-4 2,4-hexadiene-1-ol 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 
• 42125-10-0 (2Z)-pent-2-en-1-yl acetate 
• 488-10-8 jasmone 
• 128455-37-8 2-iodo-3-methyl-2-cyclopenten-1-one 
• 488-10-8 cis-jasmone 
• 74420-26-1 cis-3-hexen-1-yl phenyl sulfone 
• 74420-33-0 (Z)-4-Benzenesulfonyl-1-(2-methyl-[1,3]dioxolan-2-yl)-non-6-en-3-one 
• 74420-27-2 (Z)-6-(Phenylsulfonyl)-8-undecene-2,5-dione 
• 74420-30-7 (Z)-6-(Phenylsulfonyl)-2-hydroxyundec-8-en-5-one 

Relevant academic research and scientific papers

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

The synthesis of jasmone and related jasmonoids and pyrethroids is described. These compounds play a defensive role in plants and share a common cyclopentenone core with variations in the side chains. Jasmone, cinerone, allylrethrone, and derivatives were synthesized through -allyl palladium cross-coupling of stannane derivatives. With selective hydrogenation, dihydrojasmone, and dihydrocinerone were also synthesized.

Oxidation of alkenes with non-heme iron complexes: Suitability as an organic synthetic method

In the course of a preliminary study to determine the preparative value and the synthetic applications of the non-heme iron(II) complexes Fe(bpmen)(OTf)2 and Fe(tpa)(OTf)2, in particular the oxidation of alkenes by using hydrogen peroxide as the terminal oxidant, we have found significant differences in catalyst behavior. After several attempts it was clear that the preparative relevance of the oxidation processes was linked to the concentration of the catalyst and optimal results were obtained when the concentration value was 5 mol %. At that concentration, the Fe(bpmen)(OTf)2 catalyst mostly gave rise to mixtures of the epoxide and the trans-dihydroxylation products formed by water-assisted hydrolytic cleavage of the epoxides. Furthermore, the use of the tripodal ligand tpa led to cis dihydroxylation products. When deactivated olefins were used as substrates for the oxidation reaction, the cis-diols were obtained exclusively, although with modest conversions, regardless of the catalyst used.

Process for preparing oxocyclopentene derivatives

A process for preparing oxocyclopentenes of the formula: STR1 wherein R1 is hydrogen, lower alkyl or lower alkenyl and R2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl, which comprises subjecting a furan-carbinol of the formula: STR2 wherein R1 is as defined above and R3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl to rearrangement, subjecting the resultant hydroxycyclopentenone of the formula: STR3 wherein R1 and R3 are each as defined above to hydrogenation and subjecting the resulting hydroxycyclopentanone of the formula; STR4 wherein R1 and R2 are each as defined above to dehydration.

NEW METHOD FOR SYNTHESIS OF cis-JASMONE

A new method for the synthesis of cis-jasmone was developed on the basis of the regioselective and stereoselective alkylation of the enolic isobutyl ether of 1,3-cyclopentanedione.

A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES

An efficient and practical method for the stereospecific synthesis of olefins from vicinal diols via the corresponding 2-methoxy-1,3-dioxolanes is reported.

Process for preparing 2-cyclopentenone derivatives

A novel process for preparing 2-cyclopentenones of the formula: STR1 wherein R1 is hydrogen, alkyl or alkenyl and R2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: STR2 wherein R1 and R2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: STR3 wherein R1 and R2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: STR4 wherein R1 and R2 are each as defined above and R is hydrogen or C1 -C4 alkyl and subjecting the resulting mixture to reduction.

A Short Synthesis of Dihydrojasmone, cis- and trans-Jasmones

The titled jasmones were synthesized from N,N'-dimethyl-2-oxo-1,3-propanedisulfoanilide, a new three carbon building block for organic preparation.

Synthesis of cis-Jasmone via the Retroaldol-aldol Condensation of 3-(cis-3-hexenyl)-2-cyclopentenone in an Autoclave

cis-Jasmone was efficiently synthesized from 2-cyclopentenone.The treatment of cyclopentenone with sodium p-toluenesulfinate gave 3-(p-tolylsulfonyl)cyclopentanone in a 92.5percent yield.The alkylation of the sulfone, after the protection of the ketone, with cis-1-bromo-3-hexene, followed by desulfonylation with 5percent hydrochloric acid in tetrahydrofuran, afforded 3-(cis-3-hexenyl)-2-cyclopentenone in a good yield.The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5percent sodium hydroxide yielded cis-jasmone in a 80percent yield.

New Routes to cis-Jasmone and Dihydrojasmone via 1,4-Diketones Exploiting the Mobile Activating Sulfonyl Group

cis-Jasmone(1a) and dihydrojasmone(1b) are synthesized starting from cis-3-hexen-1-yl phenyl sulfone (6a) and n-hexyl phenyl sulfone (6b), respectively, through 1,4-diketones 3a,b.The key intermediates in these syntheses are the diketo sulfones 7a,b, which are prepared by two methods.The reaction of dilithiosulfones 12a,b with γ-valerolactone in tetrahydrofuran in the presence of hexamethylphosphoramide at -78 deg C gives the hydroxy keto sulfones 13a,b in satisfactory yields and the successive oxidation of these compounds with Jones reagent in acetone affords 7a,b in very good yields.On the other hand, the reaction of 12a,b with ethyl levulinate ethylene ketal gives the partially protected diketo sulfones 17a,b, from which 7a,b are obtained by removal of the protecting group.Cleavage of the carbon-sulfur bond in 7a,b, accomplished by aluminum amalgam in aqueous tetrahydrofuran, affords 3a,b which are then cyclized to 1a,b by heating over basic alumina in benzene.