109667-02-9

Usage

Uses

Used in Flavor and Fragrance Industry:
(R)-2-(1-Cyclopentenyl) acetate is used as a key ingredient for adding fruity and floral notes to various consumer products. Its natural origin and appealing scent make it a popular choice in the flavor and fragrance industry.
Used in Perfumery:
In the perfumery sector, (R)-2-(1-Cyclopentenyl) acetate is utilized as a component in the creation of perfumes, enhancing their overall aroma and providing a unique, pleasant scent.
Used in Cosmetics:
(R)-2-(1-Cyclopentenyl) acetate is also employed in the cosmetics industry, where it serves as a fragrance ingredient, adding a pleasant and natural scent to various cosmetic products.
Used in Food Flavorings:
(R)-2-(1-Cyclopentenyl) acetate is used as an additive in the food industry to impart a fruity and floral flavor to different types of food products, enhancing their taste and consumer appeal.
Used in Pharmaceutical Research:
Due to its potential anti-inflammatory and antioxidant properties, (R)-2-(1-Cyclopentenyl) acetate is being studied for its possible applications in the pharmaceutical industry, particularly for the development of new drugs targeting inflammation and oxidative stress-related conditions.

Upstream product

• 109431-72-3 (+)-(R)-2-cyclopentene-1-ol 
• 108-24-7 acetic anhydride 
• 10481-34-2 2-bromo-2-cyclopenten-1-one 
• 65756-04-9 trans-(±)-2-(phenylthio)cyclopentanol 
• 724435-49-8 Naphthalene-1-carboxylic acid (R)-cyclopent-2-enyl ester 
• 62247-42-1 (S)-(cyclopent-2-en-1-yl)acetate 
• 10387-40-3 potassium thioacetate 
• 20657-21-0 3-acetoxycyclopent-1-ene 
• 108-22-5 Isopropenyl acetate 
• 57857-90-6 (+/-)-trans-2-iodocyclopentanol 
• 154617-12-6 (1R, 2R)-2-(phenylthio)cyclopentyl acetate 
• 109431-73-4 (R)-2-bromo-2-cyclopenten-1-ol 

Downstream Products

• 62247-42-1 (S)-(cyclopent-2-en-1-yl)acetate 

Relevant academic research and scientific papers

Synthesis of Some Mimics of Nucleoside Triphosphates

The nucleotide analogues 10, 13, 14 and 20 have been synthesised; the latter phosphonate was converted into the diphosphoryl-phosphonate 21 and this compound was shown to be a potent inhibitor of HIV-coded reverse transcriptase.

Palladium-catalyzed enantioselective allylic alkylation of thiocarboxylate ions: Asymmetri synthesis of allylic thioesters and memory effect/dynamic kinetic resolution of allylic esters

The palladium-catalyzed allylic alkylation of KSAc and KSBz with racemic cyclic and acyclic allylic esters by using N,N'-(1R,2R)-1,2-cyclohexandiylbis[2-(diphenylphosphino)-benzamide] as ligand frequently gave the corresponding allylic thioesters with high ee values and yields. The reaction of the cyclic allylic carbonates with KSAc in the presence of H20 was accompanied by a partial palladium-catalyzed enantioselective "hydrolysis" of the substrates with formation of the corresponding enantioenriched allylic alcohols. The degree of the "hydrolysis" was strongly dependent on the solvent and the thiocarboxylate ion. Highly selective kinetic resolutions (KRs) were observed in the palladium-catalyzed reaction of the racemic cyclohexenyl and cycloheptenyl acetates with KSAc. While the KR of the cyclohexenyl acetate is characterized by a selectivity factor S = 72 ± 19, that of the cycloheptenyl acetate afforded (R)-cycloheptenyl acetate of ≥ 99% ee in 48% yield and (S)-cycloheptenyl thioacetate of 98% ee in 50% yield. The palladium-catalyzed reaction of the racemic cyclopentenyl acetate with KSAc showed a strong "memory effect" (ME), that is, both enantiomers reacted with different enantioselectivities. The ME was probed by studying the palladium-catalyzed reactions of both the matched acetate of ≥ 99% ee and the mismatched acetate of ≥ 99% ee with KSAc. The acetates not only reacted with different enantioselectivities and rates but also suffered an unexpected and concomitant palladium-catalyzed racemization in the presence of the chiral ligand. This led in the case of the mismatched acetate to a temporary dynamic kinetic resolution (DKR) that featured a racemization of the mismatched acetate by the chiral catalyst. Studies of the palladium-catalyzed reaction of the racemic cyclopentenyl acetate, carbonate, and naphthoate with KSAc in the presence of the chiral ligand also showed the ME to be strongly dependent on the nucleofuge. This also allowed the synthesis of (S)-cyclopentenyl thioacetate of 92% ee in high yield from the racemic cyclopentenyl naphthoate.

Simple, Catalytic Enantioselective Syntheses of Estrone and Desogestrel

Highly enantioselective and very short syntheses of the bioactive forms of estrone (3) and desogestrel (4) are described using a chiral oxazaborolidinium catalyst (2) in the key initial step. Enantiomerically pure estrone was synthesized in eight steps from the readily available starting materials diene 5 and α,β-enal 6 via intermediates 8 and 9. Desogestrel was synthesized using a similar strategy from diene 5 and α,β-enal 11 via intermediates 12-17. The efficient syntheses of the chiral catalyst 2 and its enantiomer are also presented. Copyright

Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification

Optically pure (R)-2-cycloalken-1-ols were synthesized via highly enantioselective lipase-catalyzed transesterification of 2-substituted cycloalkanols.

(+)-1(S),5(R),8(S)-8-PHENYL-2-AZABICYCLOOCTAN-8-OL N,O-METHYLBORONATE (2) AND ITS ENANTIOMER, CHIRAL CHEMZYMES WHICH SERVE AS CATALYSTS FOR THEIR OWN ENANTIOSELECTIVE SYNTHESIS

An efficient synthesis of (+)-1(S),5(R),8(S)-8-phenyl-2-azabicyclooctan-8-ol (1) and its enantiomer is described.The B-methyloxaborolidine derivatives (2) of these amino alcohols are excellent catalysts (chemzymes) for the enantioselective reductio