53210-16-5

Basic information

• Product Name: (E)-(4-cyclohexylbut-3-en-2-yl)benzene
• Synonyms: (E)-(4-cyclohexylbut-3-en-2-yl)benzene
• CAS NO: 53210-16-5
• Molecular Weight: 214.351
• Mol File: 53210-16-5.mol

Chemical Properties

• CAS DataBase Reference: (E)-(4-cyclohexylbut-3-en-2-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(4-cyclohexylbut-3-en-2-yl)benzene(53210-16-5)
• EPA Substance Registry System: (E)-(4-cyclohexylbut-3-en-2-yl)benzene(53210-16-5)

Safety Data

• Hazardous Substances Data: 53210-16-5(Hazardous Substances Data)

Upstream product

• 1352656-39-3 (E)-tert-butyl 4-cyclohexylbut-3-en-2-yl carbonate 
• 98-80-6 phenylboronic acid 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 25203-83-2 (E)-1-cyclohexyl-1,3-butadiene 

Relevant articles and documents

Allyl-aryl coupling of allylic carbonates with arylboronic acids catalyzed by palladium nanoparticles in ionic liquid

A practical and greener process for the allyl-aryl coupling of allylic carbonates with arylboronic acids catalyzed by in situ generated palladium nanoparticles (PdNPs) in ionic liquid (IL) has been described. The PdNPs showed high catalytic activity for the coupling reaction in the IL to afford allyl-aryl coupling products in good to high yields with complete regio- and E/Z selectivities. The PdNPs were readily immobilized in the IL phase and the catalyst can be reused several times without significant loss of catalytic activity and stereospecificity.

Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles

The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated SN2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.

Pd-catalyzed regioselective and stereospecific Suzuki-Miyaura coupling of allylic carbonates with arylboronic acids

The Pd-catalyzed Suzuki-Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl-aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl-aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.

Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of π-Allyl palladium intermediates under oxidative conditions

A palladium-catalyzed reductive cross-coupling of 1,3-dienes with boronic esters in which a π-allyl Pd species is generated directly from a 1,3-diene via a Pd-catalyzed aerobic alcohol oxidation is reported. Both the scope of the process and the origin of a highly selective 1,2-addition are discussed.