3810-26-2

Usage

Uses

Used in Flavoring and Fragrance Industry:
3-Phenyl-2-cyclopenten-1-one is utilized as a flavoring agent in the food and beverage industry, enhancing the taste and aroma of various products. Its sweet, floral odor also makes it a popular ingredient in the production of perfumes and fragrances, contributing to their unique scents.
Used in Pharmaceutical Industry:
Due to its aromatic properties, 3-Phenyl-2-cyclopenten-1-one has potential applications in the pharmaceutical industry. It can be used in the development of drugs that require a pleasant smell or as a component in the formulation of medications.
Used in Cosmetic Industry:
In the cosmetic industry, 3-Phenyl-2-cyclopenten-1-one can be employed for its pleasant aroma, improving the sensory experience of cosmetic products. Its aromatic properties may also contribute to the development of fragrances and other scented cosmetic products.
Used as a Synthesis Intermediate:
3-Phenyl-2-cyclopenten-1-one is a valuable intermediate in the synthesis of other organic compounds. Its unique structure allows for further chemical reactions, making it a useful building block in the creation of various chemical products.

InChI:InChI=1/C11H10O/c12-11-7-6-10(8-11)9-4-2-1-3-5-9/h1-5,8H,6-7H2

Upstream product

• 34721-89-6 2-methyl-5-phenyl-furan 
• 583-05-1 1-phenylpentane-1,4-dione 
• 10487-96-4 1-phenylcyclopentanol 
• 62664-60-2 ethyl 2-benzoyl-4-oxopentanoate 
• 108-24-7 acetic anhydride 
• 67100-29-2 3-phenyl-3-phenylsulfonylcyclopentanol 
• 18152-84-6 5-bromo-2-methyl-6-oxo-4-phenyl-6H-pyran-3-carboxylic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 70-11-1 α-bromoacetophenone 
• 825-54-7 cyclopent-1-en-1-ylbenzene 
• 57951-63-0 1-(phenylethynyl)cyclopropan-1-ol 
• 26620-13-3 trans-2-Phenyl-1-carboxycyclopentanon-⁽⁴⁾ 
• 75066-57-8 3,6-Dioxo-6-phenyl-2-(triphenylphosphoranyliden)hexananilid 
• 126361-56-6 benzoyl-4 oxo-2 butylphosphonate de diethyle 

Downstream Products

• 54524-34-4 5-methyl-2-phenyl-cyclopenta-1,3-diene 
• 66374-24-1 5-benzylidene-3-phenyl-cyclopent-2-enone 
• 53812-57-0 1,3-diphenyl-1,3-cyclopentadiene 
• 2327-56-2 1-phenyl-1,3-cyclopentadiene 
• 19926-46-6 1-hydroxy-3-phenylcyclopent-2-ene 
• 80109-12-2 1-Methoxy-3-(4-phenyl-cyclopenta-1,3-dienyl)-benzene 
• 80109-15-5 1-Bromo-4-(4-phenyl-cyclopenta-1,3-dienyl)-benzene 
• 4982-34-7 1,4-diphenyl-1,3-cyclopentadiene 
• 85662-51-7 (rac)-3-phenyl-3-methylcyclopentanone 
• 16343-47-8 3-p-Chlorbenzyl-3-phenylcyclopentanon 
• 16343-46-7 3-(4-Methoxy-benzyl)-3-phenyl-cyclopentanone 
• 161838-77-3 1-methyl-3-phenyl-2-cyclopentene-1-carbaldehyde 
• 26131-82-8 (+/-)-5-methyl-3-phenyl-cyclopent-2-enone 
• 64145-51-3 (R)-3-phenylcyclopentanone 

Relevant academic research and scientific papers

A unified approach to sesquiterpenes sharing trimethyl(p-tolyl) cyclopentanes: Formal total synthesis of (±)-laurokamurene B

A unified approach to the sesquiterpenoids sharing common trimethyl(p-tolyl) cyclopentane skeleton has been disclosed via a key Stork-Danheiser sequence on a cyclopentane based vinylogous ester with aryl Grignard reagent followed by α-methylation strategy

Synthesis and thermal properties of a new styryl-functionalized pentafulvene glassy carbon precursor

The first preparation of a styryl-functionalized aryl pentafulvene 4 was carried out. In the crystal structure of 4, the packing of fulvene molecules results in the shortest intermolecular contacts between aligned vinyl groups. Thermal reactivity studies of 4 (DSC and TGA, under N2) revealed a small difference between the melting point (120°C) and the Tonset for cross-linking (125°C), and provided strong evidence for the production of a network material (net4) due to reactivity of the attached styryl group. Pyrolysis of net4 under N2 gave a glassy carbon product in low yield as revealed by powder X-ray and TGA analyses (carbon yield (TGA) of 38% (900°C)).

Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes

(Chemical Equation Presented) An efficient method for preparing a series of polysubstituted cyclopentenones from TIPS-vinylketenes and Koebrich reagent has been developed in this paper. Additionally, highly substituted cyclopentenones can be prepared via

Rearrangement of 1-Alkynylcyclopropanol to 3-Substituted 2-Cyclopentenone Promoted by a Catalytic Amount of Octacarbonyldicobalt-Triphenylphosphite

The rearrangement of 1-(1-alkynyl)cyclopropanols is catalyzed efficiently by the combined use of octacarbonyldicobalt and triphenylphosphite to give 3-substituted 2-cyclopentenones in high yields.

Palladium-catalyzed intramolecular 5-endo-trig oxidative Heck cyclization: a facile pathway for the synthesis of some sesquiterpene precursors

An efficient and convenient method for the construction of substituted cyclopentenones via palladium-catalyzed intramolecular 5-endo-trig oxidative cyclization has been introduced as a powerful new strategy for the synthesis of sesquiterpenes.

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

An evaluation of palladium-based catalysts for the base-free borylation of alkenyl carboxylates

Synthesis of organoboron derivatives is a key application of catalytic cross-coupling, with the Pd-catalyzed Miyaura borylation among the most versatile methods available. We have evaluated several Pd-based systems for borylation of alkenyl acetates and p

Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates

Carboxylate esters have many desirable features as electrophiles for catalytic cross-coupling: they are easy to access, robust during multistep synthesis, and mass-efficient in coupling reactions. Alkenyl carboxylates, a class of readily prepared non-aromatic electrophiles, remain difficult to functionalize through cross-coupling. We demonstrate that Pd catalysis is effective for coupling electron-deficient alkenyl carboxylates with arylboronic acids in the absence of base or oxidants. Furthermore, these reactions can proceed by two distinct mechanisms for C?O bond activation. A Pd0/II catalytic cycle is viable when using a Pd0 precatalyst, with turnover-limiting C?O oxidative addition; however, an alternative pathway that involves alkene carbopalladation and β-carboxyl elimination is proposed for PdII precatalysts. This work provides a clear path toward engaging myriad oxygen-based electrophiles in Pd-catalyzed cross-coupling.

Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process

A chemo-enzymatic catalytic system, comprised of Bobbitt's salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcohols into the corresponding enones under an Oxygen atmosphere in aqueous media. The yields were in most cases quantitative, especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcohols bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation. Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione. The rearrangement of exocyclic allylic alcohols was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO+BF4?)/laccase catalysed oxidative rearrangement was combined with the ene-reductase/alcohol dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity. (Figure presented.).

Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio- and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through Cyclodimerization of 1-Ethynyl-2-propenyl Esters

Gold(I) complexes bearing sterically demanding phosphine ligands such as tBuXphos catalyze the cascade Rautenstrauch rearrangement/[4 + 3] cycloaddition of 1-ethynyl-2-propenyl esters. The reaction provides an efficient and straightforward rout