4994-16-5

Usage

Uses

Used in Pharmaceutical Industry:
4-PHENYL-1-CYCLOHEXENE is used as a pharmaceutical compound for its ability to reduce renal oxidative stress. This property makes it a potential candidate for the development of treatments targeting kidney-related conditions and diseases.
Used in Chemical Industry:
As a volatile organic compound, 4-PHENYL-1-CYCLOHEXENE can be utilized in various chemical processes and reactions, contributing to the synthesis of other compounds and materials. Its specific applications may vary depending on the requirements of the chemical industry.

InChI:InChI=1/C12H14/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-5,7-8,12H,6,9-10H2

Upstream product

• 100-42-5 styrene 
• 590-19-2 2,3-dimethylbutene 
• 1466-72-4 4-phenyl-1-bromocyclohexane 
• 106-99-0 buta-1,3-diene 
• 142-45-0 Acetylenedicarboxylic acid 
• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 591-50-4 iodobenzene 
• 110-83-8 cyclohexene 
• 114895-10-2 phenylazoxy phenyl sulphone 
• 5437-46-7 trans-4-phenylcyclohexanol 
• 17763-67-6 Phenyl triflate 
• 170800-47-2 C₁₄H₂₀O 
• 64422-96-4 trans-(4-methoxycyclohexyl)benzene 
• 64422-95-3 cis-4-Phenylcyclohexanolmethylether 

Downstream Products

• 38671-80-6 4-phenyl-1,2-cyclohexanediol 
• 56709-94-5 N-phenyl-2-phenyl-3-[(phenylamino)methylene]-1-cyclohexene-1-methanimine hydrochloride 
• 92-52-4 biphenyl 
• 56376-63-7 3-phenyl-adipic acid 

Relevant academic research and scientific papers

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

The effect of Al2O3 and ionic liquids in palladium catalyzed arylation of cyclohexene. Interaction of Hg(0) with immobilized palladium

Three-component systems containing Pd(OAc)2, Al2O3, and an IL (IL = ionic liquid) were applied in the Heck arylation of cyclohexene. The highest productivity and selectivity to 4-phenylcyclohexene was noted in reaction catalyzed by Pd/Al2O3 in the presence of a small amount of an IL, dimethyldidodecylammonium lactate (C). The addition of Al2O3 alone to the reaction catalyzed by soluble precursors, PdCl2(PhCN)2 or Pd(OAc)2 and IL, remarkably increased conversion to 4-phenylcyclohexene. Hg(0) inhibited the reaction catalyzed by Pd/Al2O3 by formation of Pd-Hg amalgam immobilized on Al2O3. SEM/EDX studies of Pd/Al2O3 performed after treatment with Hg(0) showed that the IL modified the surface properties of Pd/Al2O3.

Mechanistic insights into Br?nsted acid-induced nucleophilic substitution of aliphatic imidazole carbamate with halide ions

Herein we report interesting reactivity of imidazole carbamate towards nucleophilic substitution with halide ions under Br?nsted acidic conditions. Depending upon reaction conditions, halide ions could readily attack the carboxyl position and trigger decarboxylative alkyl halide formation. Alternatively, halide ions were also found to competitively undergo nucleophilic acyl substitution, which ultimately results in the generation of carbonate dimerization product.

A mild method for eliminating alkyl ethers to alkenes

A method for the conversion of methyl ethers into alkenes is described. In a one-step and mild procedure, both conjugated and isolated cyclic alkenes are accessible in mostly good yields using triflic anhydride in combination with triethylamine. This elimination procedure can also be applied to ethyl and benzyl ethers.

Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins

In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright

Copper-catalyzed alkene arylation with diaryliodonium salts

Alkenes and arenes represent two classes of feedstock compounds whose union has fundamental importance to synthetic organic chemistry. We report a new approach to alkene arylation using diaryliodonium salts and Cu catalysis. Using a range of simple alkenes, we have shown that the product outcomes differ significantly from those commonly obtained by the Heck reaction. We have used these insights to develop a number of new tandem and cascade reactions that transform readily available alkenes into complex arylated products that may have broad applications in chemical synthesis.

Selective heck arylation of cyclohexene with homogeneous and heterogeneous palladium catalysts

Palladium catalysts containing Pd(II) supported on Al2O 3 and alumina-based mixed oxides, Al2O3- ZrO2, Al2O3-CeO2, and Al 2O3-Fe2O3, are very effective in the Heck coupling of iodobenzene with cyclohexene in DMF solution. The best results, up to 81% of monoarylated products with a selectivity to 4-phenylcyclohexene (3) close to 90% were obtained with KOH as a base. The catalytic activity of palladium supported on aluminabased oxides was compared with that of homogeneous precursors, such as Pd(OAc)2 and PdCl 2(PhCN)2, used in [Bu4N]Br as the reaction medium. Under such conditions homogeneous systems were more selective and produced up to 60% of monoarylated products with a selectivity to 3 close to 60%. Copyright

Complete study of the pyrolysis and gasification of scrap tires in a pilot plant reactor

The pyrolysis and gasification of tires was investigated in a pilot plant reactor provided with a system for condensation of semivolatile matter. The study comprised experiments at 450°, 750°, and 1000°C both in nitrogen and 10% oxygen atmospheres. In the gas phase, only methane and benzene yields increased with temperature until 1000°C. In the liquids, the main components were styrene, limonene, and isoprene. The solid fraction (including soot) increased with temperature. Zinc content of the char decreased with increasing temperature. Analysis of the surface area of the solids showed that the area was similar in all cases to that of a commercial carbon black. The higher surface of the soot with respect to the chars was observed. The results coincided with published findings, i.e., kinetic severity function values would produce 0.2% of methane at 450°C and 4.5% at 750°-1000°C.

Oxygen-promoted Pd(II) catalysis for the coupling of organoboron compounds and olefins

(Matrix presented) Reported herein is a mild and efficient Pd(ll) catalysis, leading to the formation of carbon-carbon bonds between a broad spectrum of organoboron compounds and alkenes. Molecular oxygen was employed to reoxidize the resultant Pd(0) species back to Pd(ll) during catalytic cycles. This oxygen protocol promoted the desired Pd(ll) catalysis, whereas it retarded competing Pd(0) catalytic pathways such as Heck or Suzuki couplings.

Heck reactions in hydrothermal, sub-critical water: Water density as an important reaction variable

Heck coupling reactions of iodobenzene and cyclohexene in sub-critical water illustrate the importance of water density as a reaction variable. Altering the water density from 0.03 to 0.84 g/mL and the reaction pressure from 30 to greater than 213 bar at 225°C changed both product and isomer yields. The multiple physical effects of water density were also explored by the addition of ionic salts. Changing the isothermal state of the liquid water, measurably altered coupling reaction pathways suggesting that changes in solvent-solute interactions can influence transition states favoring some configurations and disfavoring others.