4894-75-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylcyclohexanone is used as a key intermediate in the synthesis of CCR2 antagonists, which are crucial for the treatment of various disease states such as rheumatoid arthritis and atherosclerosis. Its role in the synthesis process is to provide a structural framework that can be further modified to create the desired therapeutic agents.
Used in Chemical Industry:
4-Phenylcyclohexanone is used in the preparation of coumarins, which are important organic compounds with a wide range of applications, including pharmaceuticals, agrochemicals, and dyes. The synthesis involves dehydrogenation and Heck coupling reactions, showcasing the versatility of 4-Phenylcyclohexanone in various chemical transformations.
Used in Polymer Industry:
4-Phenylcyclohexanone was used in the preparation of a new cardo diamine monomer, 1,1-bis[4-(4-aminophenoxy)phenyl]-4-phenylcyclohexane bearing a 4-phenylcyclohexylidene unit. This monomer can be further utilized in the development of advanced polymer materials with specific properties and applications.
General Description:
4-Phenylcyclohexanone is known for its reactivity in various chemical reactions, such as the Ruthenium-catalyzed reaction with tributylamine, which yields 2-butyl-4-phenylcyclohexanone and 2,6-dibutyl-4-phenylcyclohexanone. Additionally, the Wittig reaction of 4-Phenylcyclohexanone with (carbethoxymethylene)triphenylphosphorane under microwave irradiation has been investigated, further demonstrating its potential in synthetic chemistry.

InChI:InChI=1/C12H14O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-5,11H,6-9H2

Upstream product

• 930-68-7 cyclohexenone 
• 25163-93-3 8-phenyl-1,4-dioxaspiro[4,5]decane 
• 827-52-1 1-phenyl-1-cyclohexane 
• 5769-13-1 4-phenyl-cyclohexanol 
• 1444-93-5 4-phenyl-1,2-cyclohexanedicarboxylic acid 
• 108164-51-8 1,1-diethylthio-4-phenylcyclohexane 
• 128881-92-5 C₂₄H₂₄S₂ 
• 29916-50-5 C₁₂H₁₄NO₂^(1-) 
• 139021-96-8 9-phenyl-1,5-dithia-spiro[5.5]undecane 
• 92-69-3 4-Phenylphenol 
• 86724-17-6 4-methyl-N’-(4-phenylcyclohexylidene)benzenesulfono hydrazide 
• 27070-24-2 (3-bromo-1-(2-bromoethyl)-propyl)benzene 
• 250293-45-9 4-Phenylcyclohexanone N-phenylhydrazone 
• 106592-05-6 8-phenyl-1,4-dithia-spiro[4.5]decane 

Downstream Products

• 1079-68-1 (+/-)-trans-2-bromo-4-phenyl-cyclohexanone 
• 109337-60-2 4-phenylcyclohexan-1-d-1-ol 
• 102162-15-2 1-(2-Methoxy-phenyl)-4-phenyl-cyclohexanol 
• 5977-10-6 Biligen 
• 33384-15-5 1-(2,2'-Dimethyl-4-biphenylyl)-4-phenylcyclohexen 
• 37416-23-2 2-(4-Phenyl-cyclohex-1-enyl)-propionic acid ethyl ester 
• 28125-94-2 1-(4-phenyl-cyclohex-1-enyl)-pyrrolidine 
• 2862-92-2 1-methyl-4-phenylcyclohexan-1-ol 
• 152387-04-7 (R)-(4-Phenylcyclohexen-1-enyloxy)trimethylsilane 
• 115880-04-1 ethyl 2-(4-phenylcyclohexylidene)acetate 
• 87996-26-7 1-tert-Butoxymethyl-4-phenyl-cyclohexanol 
• 122948-47-4 4-phenylcyclohex-1-enyl trifluoromethanesulfonate 
• 113035-72-6 1-<1-(Methylthio)ethyliden>-4-phenylcyclohexan 
• 138956-44-2 hexahydro-5-phenyl-1-benzyl-2H-azepin-2-one 

Relevant academic research and scientific papers

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Deciphering Reactivity and Selectivity Patterns in Aliphatic C-H Bond Oxygenation of Cyclopentane and Cyclohexane Derivatives

A kinetic, product, and computational study on the reactions of the cumyloxyl radical with monosubstituted cyclopentanes and cyclohexanes has been carried out. HAT rates, site-selectivities for C-H bond oxidation, and DFT computations provide quantitative information and theoretical models to explain the observed patterns. Cyclopentanes functionalize predominantly at C-1, and tertiary C-H bond activation barriers decrease on going from methyl- and tert-butylcyclopentane to phenylcyclopentane, in line with the computed C-H BDEs. With cyclohexanes, the relative importance of HAT from C-1 decreases on going from methyl- and phenylcyclohexane to ethyl-, isopropyl-, and tert-butylcyclohexane. Deactivation is also observed at C-2 with site-selectivity that progressively shifts to C-3 and C-4 with increasing substituent steric bulk. The site-selectivities observed in the corresponding oxidations promoted by ethyl(trifluoromethyl)dioxirane support this mechanistic picture. Comparison of these results with those obtained previously for C-H bond azidation and functionalizations promoted by the PINO radical of phenyl and tert-butylcyclohexane, together with new calculations, provides a mechanistic framework for understanding C-H bond functionalization of cycloalkanes. The nature of the HAT reagent, C-H bond strengths, and torsional effects are important determinants of site-selectivity, with the latter effects that play a major role in the reactions of oxygen-centered HAT reagents with monosubstituted cyclohexanes.

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides

As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.

Zinc substituted Keggin-type polyoxometalate on Dowex: a green heterogeneous catalyst for oxidation of alcohols in water

In this work, homogeneous and heterogeneous oxidation of alcohols by H2O2 in the presence of [(n-C4H9)4?N]5[PW11ZnO39].3H2O and [PW11ZnO39]5? supported on Dowex 22 as catalysts have been investigated. Using water as a green solvent, different alcohols were converted into the corresponding aldehydes and ketones in high to excellent yields. Dowex 22 supported polyoxometalate, PW11Zn@Dowex, was also catalyzed highly robust and selective oxidation of unsaturated alcohols. Leaching and recycling experiments on supported catalyst revealed the excellent stability and reusability of this catalytic system.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes

The use of chiral enol silanes in fundamental transformations such as Mukaiyama aldol, Michael, and Mannich reactions as well as Saegusa-Ito dehydrogenations has enabled the chemical synthesis of enantiopure natural products and valuable pharmaceuticals. However, accessing these intermediates in high enantiopurity has generally required the use of either stoichiometric chiral precursors or stoichiometric chiral reagents. We now describe a catalytic approach in which strongly acidic and confined imidodiphosphorimidates (IDPi) catalyze highly enantioselective interconversions of ketones and enol silanes. These "silicon-hydrogen exchange reactions"enable access to enantiopure enol silanes via tautomerizing σ-bond metatheses, either in a deprotosilylative desymmetrization of ketones with allyl silanes as the silicon source or in a protodesilylative kinetic resolution of racemic enol silanes with a carboxylic acid as the silyl acceptor.

Improved Process for the Palladium-Catalyzed C-O Cross-Coupling of Secondary Alcohols

An improved protocol for the Pd-catalyzed C-O cross-coupling of secondary alcohols is described. The use of biaryl phosphine L2 as the ligand was key to achieving efficient cross-coupling of (hetero)aryl chlorides with only a 20percent molar excess of the alcohol. Additionally, we observed an unusual reactivity difference between an electron-rich aryl bromide and the analogous aryl chloride, and deuterium-labeling suggested that currently unidentified pathways for reduction play an important role in explaining this disparity.

PdBr2-Catalyzed Acetal Formation of Carbonyl Compounds Using Diazophenanthrenequinone: Utility of 9,10-Phenanthrenedioxyacetal

We developed a new acetalization method of ketones and aldehydes under non-acidic conditions using diazophenanthrenequinone and PdBr2. The formed acetals that have a phenanthrene skeleton withstand under mild acidic conditions. Removal of acetals was successfully proceeded under strong acidic or oxidation conditions using aqueous ceric ammonium nitrate (CAN) to afford corresponding ketones and aldehydes.