52486-39-2

Basic information

• Product Name: (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate
• Synonyms: (R)-2,2,3-Trimethylcyclopent-3-ene-1-ethyl acetate; 3-Cyclopentene-1-ethanol, 2,2,3-trimethyl-, acetate, (theta)-
• CAS NO: 52486-39-2
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.288
• EINECS: 257-952-7
• Mol File: 52486-39-2.mol

Chemical Properties

• CAS DataBase Reference: (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate(52486-39-2)
• EPA Substance Registry System: (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate(52486-39-2)

Safety Data

• Hazardous Substances Data: 52486-39-2(Hazardous Substances Data)

Usage

Uses

Used in Perfume and Fragrance Industry:
(R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate is used as a key ingredient in the perfume and fragrance industry for its ability to provide a fruity scent to a variety of products. Its distinct odor makes it a valuable addition to the creation of various fragrances.
Used in Flavoring Industry:
In the flavoring industry, (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate is used as a flavoring agent to enhance the taste of food and beverage products. Its fruity aroma adds a delightful flavor profile to these items, making them more appealing to consumers.
Used in Household and Personal Care Products:
(R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate is also utilized in the production of household and personal care products such as soaps, detergents, and cosmetics. Its pleasant fruity scent and taste make it a suitable component for these products, contributing to their overall sensory appeal.
Used in Pharmaceutical Industry:
Additionally, (R)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate has potential applications in the pharmaceutical industry. Its properties may be harnessed for various purposes, although specific uses are not detailed in the provided materials.

Upstream product

• 70051-23-9 4r-(β-Hydroxyethyl)-2c,3,3-trimethylcyclopentanon 
• 28973-89-9 (+)-campholenic acid 
• 28973-93-5 (1R)-3c-(2-hydroxy-ethyl)-1,2,2-trimethyl-cyclopentan-r-ol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 23727-15-3 (+)-campholenic aldehyde 
• 7785-26-4 (-)-α-pinene 
• 108-24-7 acetic anhydride 
• 52437-39-5 (R)-(+)-2-(2,2,3-trimethyl-cyclopent-3-en-1-yl)ethanol 
• 108923-57-5 (1R)-3c-(2-acetoxy-ethyl)-1,2,2-trimethyl-cyclopentan-r-ol 

Downstream Products

• 52437-39-5 (R)-(+)-2-(2,2,3-trimethyl-cyclopent-3-en-1-yl)ethanol 
• 144342-22-3 (+)-(1R,E)-2,2-Dimethyl-3-<(4-tolylsulfonyl)hydrazono>cyclohexane-1-ethyl acetate 
• 144342-21-2 (+)-(1R)-2,2-Dimethyl-3-oxocyclohexane-1-ethyl acetate 
• 144342-34-7 (-)-(1R)-2,2,3-Trimethylcyclohex-3-ene-1-ethyl acetate 
• 144342-23-4 (+)-(1R)-2,2-Dimethyl-3-methylidenecyclohexane-1-ethyl acetate 
• 144342-35-8 (-)-(1R)-2,2,3-Trimethylcyclohex-3-ene-1-acetaldehyde 
• 144342-41-6 (+)-(1R)-2,2-Dimethyl-3-methylidenecyclohexane-1-acetaldehyde 
• 144342-42-7 (-)-(1R)-2,2,3-Trimethylcyclohex-3-ene-1-ethanol 
• 144342-24-5 (+)-(1R)-2,2-Dimethyl-3-methylidenecyclohexane-1-ethanol 
• 144342-30-3 (-)-(1R)-2,2-Dimethylcyclohex-3-ene-1-acetaldehyde 
• 144342-29-0 (-)-(1R)-2,2-Dimethylcyclohex-3-ene-1-ethanol 
• 104086-70-6 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanemethanol 
• 144342-28-9 (+)-(1R)-6,6-Dimethyl-5-oxocyclohex-3-ene-1-ethyl acetate 

Relevant articles and documents

Analogues of α-campholenal (=(1R)-2,2,3-trimethylcyclopent-3-ene-1- acetaldehyde) as building blocks for (+)-β-necrodol (=(1S,3S)-2,2,3- trimethyl-4-methylenecyclopentanemethanol) and sandalwood-like alcohols

To complete our panorama in structure-activity relationships (SARs) of sandalwood-like alcohols derived from analogues of α-campholenal (=(1R)-2,2,3-trimethylcyclopent-3-ene-1-acetaldehyde), we isomerized the epoxy-isopropyl-apopinene (-)-2d to the corresponding unreported α-campholenal analogue (+)-4d (Scheme 1). Derived from the known 3-demethyl-α-campholenal (+)-4a, we prepared the saturated analogue (+)-5a by hydrogenation, while the heterocyclic aldehyde (+)-5b was obtained via a Bayer-Villiger reaction from the known methyl ketone (+)-6. Oxidative hydroboration of the known α-campholenal acetal (-)-8b allowed, after subsequent oxidation of alcohol (+)-9b to ketone (+)-10, and appropriate alkyl Grignard reaction, access to the 3,4-disubstituted analogues (+)-4f,g following dehydration and deprotection. (Scheme 2). Epoxidation of either (+)-4b or its methyl ketone (+)-4h, afforded stereoselectively the trans-epoxy derivatives 11a,b, while the minor cis-stereoisomer (+)-12a was isolated by chromatography (trans/cis of the epoxy moiety relative to the C2 or C3 side chain). Alternatively, the corresponding trans-epoxy alcohol or acetate 13a,b was obtained either by reduction/esterification from trans-epoxy aldehyde (+)-11a or by stereoselective epoxidation of the α-campholenol (+)-15a or of its acetate (-)-15b, respectively. Their cis-analogues were prepared starting from (+)-12a. Either (+)-4h or (-)-11b, was submitted to a Bayer-Villiger oxidation to afford acetate (-)-16a. Since isomerizations of (-)-16 lead preferentially to β-campholene isomers, we followed a known procedure for the isomerization of (-)-epoxyverbenone (-)-2e to the norcampholenal analogue (+)-19a. Reduction and subsequent protection afforded the silyl ether (-)-19c, which was stereoselectively hydroborated under oxidative condition to afford the secondary alcohol (+)-20c. Further oxidation and epimerization furnished the trans-ketone (-)-17a, a known intermediate of either (+)-β-necrodol (=(+)-(1S,3S)-2,2,3-trimethyl-4-methylenecyclopentanemethanol; 17c) or (+)-(Z)-lancifolol (=(1S,3R,4Z)-2,2,3-trimethyl-4-(4-methylpent-3-enylidene) cyclopentanemethanol). Finally, hydrogenation of (+)-4b gave the saturated cis-aldehyde (+)-21, readily reduced to its corresponding alcohol (+)-22a. Similarly, hydrogenation of β-campholenol (=2,3,3-trimethylcyclopent-1-ene- 1-ethanol) gave access via the cis-alcohol rac-23a, to the cis-aldehyde rac-24.

Preparation of Campholenal Analogues: Chirons for the Lipophilic Moiety of Sandalwood-Like Odorant Alcohols

In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared.The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2).The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl acetate ((-)-14b), followed by intramolecular aldol condensation (Scheme 5). 13C-NMR assignments are given.