3954-12-9

Usage

Uses

Used in Fragrance Industry:
Phenyl cyclohexanecarboxylate is used as a fragrance ingredient for its floral scent, contributing to the scent profiles of various consumer products such as perfumes, lotions, and soaps. Its ability to impart a pleasant aroma makes it a valuable addition to these products.
Used in Flavor Industry:
In the food industry, phenyl cyclohexanecarboxylate serves as a flavoring agent, enhancing the taste and aroma of different food products. Its use in this industry is based on its capacity to add a distinct flavor note to the products, thereby improving their overall sensory appeal.
Safety Considerations:
While phenyl cyclohexanecarboxylate is considered safe for use in fragrances and flavors, it is important to note that in high concentrations, it may cause irritation to the skin, eyes, and respiratory system. Therefore, it is crucial to adhere to recommended usage levels to ensure safety and avoid potential adverse effects.

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 712-50-5 Cyclohexyl phenyl ketone 
• 139-02-6 sodium phenoxide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 108-95-2 phenol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 1885-14-9 phenyl chloroformate 
• 931-50-0 cyclohexylmagnesium bromide 
• 141-53-7 sodium formate 
• 110-83-8 cyclohexene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 93-58-3 benzoic acid methyl ester 
• 108-93-0 cyclohexanol 

Downstream Products

• 155397-15-2 1,1-biscyclohexanemethanol 
• 108-95-2 phenol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 134281-50-8 S-(4-methoxyphenyl) cyclohexanecarbothioate 
• 548763-46-8 N-(4-hydroxyphenyl)cyclohexanecarboxamide 
• 2719-26-8 N-phenylcyclohexanamide 
• 712-50-5 Cyclohexyl phenyl ketone 
• 38459-58-4 4-cyclohexylcarbonyl-1-hydroxybenzene 
• 18066-52-9 cyclohexyl(2-hydroxyphenyl)methanone 
• 1309610-53-4 C₂₄H₂₉NO₂ 
• 5899-19-4 o-(α-cyclohexylmethyl)phenol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 150614-90-7 (dimethyl(phenyl)silyl)(cyclohexyl)methanone 
• 75730-04-0 (dimethylphenylsilyl)-1-cyclohexylmethanol 

Relevant academic research and scientific papers

Conversion of esters to thioesters under mild conditions

We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.

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.]

An alternative route for boron phenoxide preparation from arylboronic acid and its application for C[sbnd]O bond formation

An efficient synthetic route to benzyl phenyl ether preparation has been successfully developed via a one-pot synthetic protocol utilizing a combination of arylboronic acids, hydrogen peroxide (H2O2), and benzyl halides. The whole procedure consists of two consecutive reactions, formation of boron phenoxide from arylboronic acids and its nucleophilic attack. A simple operation under mild conditions such as room-temperature ionic liquid (choline hydroxide), aerobic environment, and absence of metal- and base-catalysts has been employed. Expansion to utilize benzyl surrogates was also successfully accomplished.

Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights

Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).

Method for preparing carboxylate aryl type compound

The invention belongs to the field of drug synthesis and in particular relates to a method for preparing a carboxylate aryltype compound. The preparation method provided by the invention comprises thefollowing steps: providing a compound A of a formula a shown in the description, a compound B of a formula b shown in the description, an organic palladium complex, and a silver salt, wherein the organic palladium complex is composed of a palladium compound and a nitrogen-containing ligand; the nitrogen-containing ligand comprises an o-phenoline compound and/or a bipyridine compound; and mixing the compound A, the compound B, the organic palladium complex and the silver salt in a reaction solvent, and performing a reaction in an inert gas atmosphere, so as to obtain the carboxylate aryl typecompound of a formula I shown in the description. As the organic palladium complex and the silver salt are simultaneously used, direct selectivity C-O coupling of carboxylic acid and halogenated aromatic hydrocarbon is realized, and the method is applicable to a variety of carboxylic acid substrates and halogenated aromatic substrates, and is wide in compatibility and high in yield.

Palladium-Catalyzed Aerobic Oxidative Coupling of Amides with Arylboronic Acids by Cooperative Catalysis

The first fluoride and palladium co-catalyzed conversion of amide to ester through an aerobic oxidative coupling pathway is reported. This new approach presents a practical process that employs easily available oxygen and commercially available arylboronic acids as coupling partners, uses a wide range of N- tosylamides, and proceeds under mild reaction conditions. This protocol demonstrates broad functional group tolerance, and provides an alternative option to synthesize esters from N-tosylamides which obtained by simply N-functionalization of secondary amides.

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions

A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.

CARBOXYLIC ACID ESTER PRODUCTION METHOD

Provided is a production method whereby corresponding carboxylic acid esters can be obtained from a variety of carboxylic acids at a high yield, even under conditions using a simple reaction operation and little catalyst and even if the amount of substrate used is theoretical. A production method for carboxylic acid ester, whereby a prescribed diester dicarbonate, carboxylic acid, and alcohol are reacted in the presence of at least one type of magnesium compound and at least one type of alkali metal compound.

Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides

To explore further the practical uses of highly active manganese (Mn?), a variety of alcohols were treated with Mn?, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.