160598-47-0

Usage

Uses

Used in Fragrance Industry:
Methyl 4-cyclopentylbenzoate is used as a fragrance ingredient for its sweet, fruity aroma, contributing to the scent profiles of various consumer products such as perfumes, lotions, and cosmetics.
Used in Flavor Industry:
In the food industry, Methyl 4-cyclopentylbenzoate is utilized as a flavoring agent to impart a fruity taste to food products, enhancing their overall flavor profile.
Synthesis:
Methyl 4-cyclopentylbenzoate is typically synthesized through esterification reactions involving cyclopentylcarboxylic acid and methanol, highlighting its versatility and widespread application in both the fragrance and flavor industries.

Upstream product

• 67-56-1 methanol 
• 19936-22-2 p-cyclopentylbenzoic acid 
• 700-88-9 cyclopentylbenzene 
• 1040745-70-7 cyclopentyltrifluoro-λ⁴-borane potassium salt 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 50715-28-1 cyclopentyl chloroformate 
• 287-92-3 Cyclopentane 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 71-43-2 benzene 
• 85689-77-6 1-(4-cyclopentylphenyl)ethan-1-one 
• 137-43-9 Cyclopentyl bromide 
• 142-29-0 cyclopentene 

Downstream Products

• 171623-29-3 (4-cyclopentylphenyl)methanol 
• 40452-70-8 4-Cyclopentylbenzaldehyde 

Relevant academic research and scientific papers

Nickel-catalyzed selective oxidative radical cross-coupling: An effective strategy for inert Csp3-H functionalization

An effective strategy for inert Csp3-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp3-H arylation products in good yields.

Redox-Neutral Nickel(II) Catalysis: Hydroarylation of Unactivated Alkenes with Arylboronic Acids

Reported here is the discovery of a redox-neutral NiII/NiII catalytic cycle which is capable of the linear-selective hydroarylation of unactivated alkenes with arylboronic acids for the first time. This novel catalytic cycle, enabled

Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides

This work describes Ni-catalyzed cross-electrophile coupling of benzyl chloroformate derivatives with aryl iodides that generates a wide range of diaryl methane products. The mild reaction conditions merit the C-O bond radical fragmentation of benzyl chloroformates via halide abstraction or a single electron reduction by a Ni catalyst. This work offers a new substrate type for cross-electrophile couplings.

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling

A strategy for cross-electrophile coupling has been developed via the merger of photoredox and transition metal catalysis. In this report, we demonstrate the use of commercially available tris(trimethylsilyl)silane with metallaphotoredox catalysis to efficiently couple alkyl bromides with aryl or heteroaryl bromides in excellent yields. We hypothesize that a photocatalytically generated silyl radical species can perform halogen-atom abstraction to activate alkyl halides as nucleophilic cross-coupling partners. This protocol allows the use of mild yet robust conditions to construct Csp3-Csp2 bonds generically via a unique cross-coupling pathway.

Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides

Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.

Single-electron transmetalation: An enabling technology for secondary alkylboron cross-coupling

Single-electron-mediated alkyl transfer affords a novel mechanism for transmetalation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyltrifluoroborates with an array of aryl bromides mediated by an Ir photoredox catalyst and a Ni cross-coupling catalyst.

CROSS-COUPLING OF UNACTIVATED SECONDARY BORONIC ACIDS

Provided are methods for site- and stereo-retentive cross-couplings with unactivated secondary boronic acids, particularly useful in building block-based approach for small molecule synthesis. Also provided is a method of forming an air-stable chiral secondary boronic acid.

Mild negishi cross-coupling reactions catalyzed by acenaphthoimidazolylidene palladium complexes at low catalyst loadings

Considering that the strong σ-donor property of ylidenes derived from π-extended imidazolium salts is conducive to increasing the catalytic activity of the resulting palladium N-heterocyclic carbene complexes, robust acenaphthoimidazol-ylidene palladium complexes 3a-c with varying bulky substituted groups were prepared from the corresponding acenaphthoimidazolium chlorides by heating with PdCl2 and K2CO3 in neat 3-chloropyridine in satisfactory yields. Even at a catalyst loading as low as 0.25 mol %, complex 3a exhibited extremely high catalytic activity toward Negishi cross-coupling of alkylzinc reagents with a wide range of (hetero)aryl halides under mild reaction conditions within 30 min. Besides a great number of bromoarenes, various less expensive and inactive (hetero)aryl chlorides were coupled successfully with the alkyl- and arylzinc reagents, in which active functional groups (such as -NH2) were well tolerated even in one-pot dicoupling transformations without protection. In addition, in the case of coupling with secondary alkylzinc reagents, undesired β-hydride elimination leading to isomerized linear products was efficaciously suppressed. The catalyst system also displayed superiority in the construction of heterobiaryls through the coupling of heteroarylzinc reagents and heterocylic chloroarenes which were hardly accessible from the corresponding organoboron reagents by Suzuki-coupling reactions. Therefore, the protocol described in this paper represents a mild, general, and scalable approach to access various structurally intriguing and functionalized (hetero)aryls.

Synthesis of Certain Mesogenic Azomethines Derived from 4-Cycloalkylanilines and from 4-Cycloalkylbenzaldehydes

General procedures are described for the synthesis of members of five pairs of related homologous series of mesogenic azomethines differing in the mode of linkage of the CH=N group and containing a cycloalkyl group in a terminal position.

Properties of the Liquid Crystals Formed by Ceratin Azomethines Derived from 4-Cycloalkylanilines and from 4-Cycloalkylbenzaldehydes

The liquid crystal behaviour of four homologous series of azomethines related to the nO.m series but containing a cycloalkyl group, is reported and discussed.Many of these compounds show extensive smectic polymorphism, one member of the nO.c6 series giving rise to five smectic polymorphic modofications for which phase type assignments have been made by thermal optical microscopy.Keywords: smectic polymorphism, azomethines, cycloalkyl derivatives