58641-29-5

Usage

Uses

Used in Fragrance Industry:
[1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate is used as a fragrance and flavoring agent for its appealing scent, which is characterized by a sweet, floral, and slightly fruity aroma. It is particularly favored in the creation of perfumes, colognes, and other scented products.
Used in Flavor Industry:
In the flavor industry, [1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate is utilized to impart a pleasant taste and aroma to various food items, enhancing the sensory experience for consumers.
Used in Industrial Applications:
[1S-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexyl benzoate is also employed as a solvent or plasticizer in certain industrial applications, where its chemical properties are beneficial for specific processes or product formulations.

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 98-88-4 benzoyl chloride 
• 612-33-9 (1R,2S,4S)-2-isopropyl-4-methylcyclohexyl benzoate 
• 93-58-3 benzoic acid methyl ester 
• 15356-70-4 menthol 
• 89-83-8 thymol 
• 2216-51-5 (-)-menthol 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 65-85-0 benzoic acid 
• 4998-93-0 2,2,2-tribromoethyl benzoate 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 93-97-0 benzoic acid anhydride 
• 67392-57-8 (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester of diphenylphosphinous acid 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 2216-51-5 (-)-menthol 
• 65-85-0 benzoic acid 
• 125553-48-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-cyanobenzoate 
• 2315-68-6 propyl benzoate 
• 93-89-0 benzoic acid ethyl ester 
• 52154-24-2 (R)-p-tolylsulfinylacetophenone 
• 78687-13-5 (S)-2-p-tolylsulfinylmethylphenyl ketone 

Relevant academic research and scientific papers

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights

Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.

Chemoselective Tertiary C?H Hydroxylation for Late-Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis

Aromatic and heterocyclic functionality are ubiquitous in pharmaceuticals. Herein, we disclose a new Mn(PDP) catalyst system using chloroacetic acid additive capable of chemoselectively oxidizing remote tertiary C(sp3)?H bonds in the presence of a broad range of aromatic and heterocyclic moieties. Although catalyst loadings can be lowered to 0.1 mol% under a Mn(PDP)/acetic acid system for aromatic and non-basic nitrogen heterocycle substrates, the Mn(PDP)/chloroacetic acid system generally affords 10–15% higher isolated yields on these substrates and is uniquely effective for remote C(sp3)?H hydroxylations in substrates housing basic nitrogen heterocycles. The demonstrated ability to perform Mn(PDP)/chloroacetic acid C(sp3)?H oxidations in pharmaceutically relevant complex molecules on multi-gram scales will facilitate drug discovery processes via late-stage functionalization. (Figure presented.).

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Base-catalyzed selective esterification of alcohols with unactivated esters

A practical and efficient base-catalyzed esterification has been developed for the facile synthesis of a broad range of esters from simple alcohols with unactivated tert-butyl esters. This protocol could be conducted at mild conditions, providing esters in high to excellent yields with good functional tolerance. Mechanistic studies provided evidence of an exchange of the tert-butyl alkoxide metal with the alcohol, producing a new alkoxide to participate in the transesterification reaction.

Fluoride-Catalyzed Esterification of Amides

In recent years, it has been demonstrated that amide carbon–nitrogen bonds can be activated and selectively cleaved using transition metal catalysts. However, these methodologies have been restricted to specific amides; a one-to-one relationship exists between the catalytic system and the amides and also uses large amounts of transition-metal catalysts and ligands. Hence, we now report a general strategy for esterification of common amides using fluoride as a catalyst. This method shows high functional group tolerance, and notably it requires only a slight excess of the alcohol nucleophile, which is a rare case in transition-metal-free amide transformations. Moreover, this approach may provide a new understanding for further studies on esterification of amides and is expected to stimulate the development of alternative methods for direct functionalization of amides.

Kinetic Modeling of the Nickel-Catalyzed Esterification of Amides

Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10-20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modeling can be used strategically to overcome this problem, specifically within the context of the Ni-catalyzed conversion of amides to esters. The successful application of this methodology to a multigram-scale coupling, using only 0.4 mol % Ni, highlights the impact of this endeavor.