16491-63-7

Usage

General Description

Allyl cyclohexanecarboxylate is an organic compound with the chemical formula C10H16O2. It is commonly used in the fragrance and flavor industry due to its sweet, fruity, and floral aroma. The chemical is often used in the production of perfumes, soaps, and other personal care products. It is also used as a flavoring agent in food and beverages. Allyl cyclohexanecarboxylate is a clear, colorless liquid with a low volatility and a high boiling point, making it suitable for a wide range of applications. While it is generally considered safe for use in consumer products, it should be handled and stored with care due to its potential irritant and sensitizing properties.

InChI:InChI=1/C10H16O2/c1-2-8-12-10(11)9-6-4-3-5-7-9/h2,9H,1,3-8H2

Upstream product

• 107-18-6 allyl alcohol 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 24850-33-7 allyltributylstanane 
• 106-95-6 allyl bromide 
• 29548-87-6 1-bromocyclohexanecarboxylic acid chloride 
• 60718-45-8 1-cyclohexanecarbonyl-1H-imidazole 
• 14593-43-2 benzyl allyl ether 
• 107-05-1 3-chloroprop-1-ene 
• 1196662-63-1 allyl 1-bromocyclohexanecarboxylate 
• 70659-83-5 N-allylcyclohexanecarboxamide 
• 72963-31-6 dimethyl 1,1-cyclohexanedicarboxylate 
• 357604-43-4 prop-2-yn-1-yl cyclohexanecarboxylate 
• 108233-78-9 diallyl 1,1-cyclohexanedicarboxylate 

Downstream Products

• 98-89-5 Cyclohexanecarboxylic acid 
• 57013-02-2 (Z)-1,2-dicyclohexylethylene 
• 123-38-6 propionaldehyde 
• 1384266-46-9 (Z)-prop-1-enyl cyclohexanecarboxylate 
• 1384266-45-8 (E)-prop-1-enyl cyclohexanecarboxylate 
• 4404-61-9 cyclohexyldiphenylmethanol 

Relevant academic research and scientific papers

Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling

A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access to valuable chiral β-fluoroalkyl arylalkanes with high efficiency and excellent enantioselectivity. The mild conditions allow for a broad substrate scope as well as good functional group toleration.

Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst

A safe, facile and low-leaching (up to 0.04ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.

An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism

A method involving iron catalyzed acylative cleavage of cyclic and acyclic ethers with acyl/aroyl chlorides has been studied to produce chloroesters and esters respectively. Examination of the scope revealed that less electron rich alkyl group in unsymmetric, acyclic ether was acylated while the chloride derived from the counterpart moiety was volatile and difficult to isolate. In contrast, α-branched cyclic ethers were converted to the corresponding primary ester and secondary chloride. Steric hindrance of ether also plays an important role in acylative C-O bond cleavage. The mechanism of ether cleavage is proposed to involve a single electron initiated SN1 dissociative pathway.

[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters

The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.

Use of diethoxymethane as a solvent for phase-transfer esterification of carboxylic acids

The esterification of carboxylic acids with selected primary alkyl halides in diethoxymethane (DEM) utilizing solid-liquid phase-transfer catalysis has been studied. The use of DEM as the solvent simplifies the process in that a single solvent can be used for both reaction and workup.

Indium-mediated Reformatsky-Claisen rearrangement

A new variant of the Reformatsky-Claisen rearrangement is described. The reaction of substituted allyl α-bromoacetates with indium and indium(III) chloride under ultrasonication provides a general entry into the functionalized synthon.

Irreversible catalytic ester hydrolysis of allyl esters to give acids and aldehydes by homogeneous ruthenium and ruthenium/palladium dual catalyst systems

An irreversible hydrolysis reaction of allyl esters (1) into carboxylic acids (2) and propanal (3) was achieved with a ruthenium/palladium (Ru/Pd) dual catalyst system. The optimized catalysts consists of a 1:1:1 mixture of (cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate {[RuCp(MeCN)3] PF6}, bis(acetonitrile)palladium dichloride [PdCl2(MeCN)2] and 1,6-bis(diphenylphosphanyl)hexane (DPPHex). The reaction proceeds via isomerization of allyl esters to 1-propenyl esters and hydrolysis of them to give 2 and 3. The first isomerization step was virtually catalyzed by the Ru components and the second hydrolysis step was mainly catalyzed by the Pd components. The optimized bidentate phosphine (DPPHex) which has long alkylene chain effectively generates two vacant sites on the Ru centers by bridging coordination. When a chelating bidentate phosphine such as DPPE was employed, only one vacant site remained on the Ru center and resulted in a low activity. This chelating Ru complex of DPPE formed even in the presence of 2 equivalents of Ru or additional 1 equivalent of Pd. These differences in coordination behaviour between DPPHex and 1,2- bis(diphenylphosphanyl)ethane (DPPE) cause the differences of the catalytic activity in the first step. The phosphine coordination to Pd center slightly decreases the activity of second hydrolysis step but which was compensated by the increasing of the stability of Pd. On the whole, the optimized Ru/Pd dual catalyst system exhibited good performances on the irreversible hydrolysis of allyl esters.

A new variant of Reformatsky-Claisen rearrangement mediated by indium chloride

A new variant of Reformatsky - Claisen rearrangement is described. The reaction of an allyl a-bromo ester in the presence of indium(I) chloride provides a general entry into the functionalized synthon. Georg Thieme Verlag Stuttgart.

THE SYNTHESIS, CHARACTERISATION AND REACTIVITY OF SOME LEAD(IV) CARBOXYLATES

A detailed examination of the preparation, characterisation and reactivity of a range of lead(IV) carboxylates is reported.The replacement of the acetate ligands of lead(IV) tetraacetate by other carboxylates gives the lead(IV) tetracarboxylates 1-16, which have usually been found to be more stable than lead tetraacetate with respect to hydrolysis.These compounds react with allyltributylstannane to give high yields of the corresponding allyl esters 20-34 under mild conditions.