36040-03-6

Usage

Uses

Used in Organic Chemistry:
2,6-Dibenzylcyclohexanone is utilized as a reactant in various synthesis processes within the field of organic chemistry. Its structural properties make it a valuable component in creating a range of chemical products.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,6-Dibenzylcyclohexanone is employed as a building block in the development of new drugs. Its unique structure contributes to the creation of potential medicinal compounds.
Used in Agrochemical Production:
2,6-Dibenzylcyclohexanone also finds application in the agrochemical sector, where it is used in the synthesis of various agrochemicals, contributing to the development of products for agricultural use.
Used in Specialty Chemicals:
2,6-Dibenzylcyclohexanone is leveraged in the production of specialty chemicals, which are tailored for specific industries and applications, highlighting its versatility in chemical synthesis.
Used in the Food Industry as a Flavoring Agent:
Capitalizing on its aromatic properties, 2,6-Dibenzylcyclohexanone is used as a flavoring agent in the food industry, adding unique taste profiles to various food products.
Safety Note:
It is important to handle 2,6-Dibenzylcyclohexanone with caution due to its potential to cause skin and eye irritation. Moreover, it is harmful if ingested or inhaled, necessitating proper safety measures during its use and manipulation.

InChI:InChI=1/C20H22O/c21-20-18(14-16-8-3-1-4-9-16)12-7-13-19(20)15-17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15H2

Upstream product

• 64-17-5 ethanol 
• 897-78-9 2,6-bis(phenylmethylene)cyclohexanone 
• 7382-09-4 cis-2,6-bis(phenylmethyl)cyclohexanone 
• 67-56-1 methanol 
• 71-36-3 butan-1-ol 
• 7647-01-0 hydrogenchloride 
• 141-52-6 sodium ethanolate 
• 108-94-1 cyclohexanone 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 7664-93-9 sulfuric acid 
• 3849-14-7 (+/-)-2t,6c-Dibenzyl-cyclohexanol 
• 64-19-7 acetic acid 
• 71-43-2 benzene 

Downstream Products

• 7382-09-4 cis-2,6-bis(phenylmethyl)cyclohexanone 
• 3849-14-7 (+/-)-2t,6c-Dibenzyl-cyclohexanol 
• 7382-13-0 2,2,6,6-tetrabenzyl-cyclohexanone 
• 97156-81-5 2,2,6-tribenzyl-cyclohexanone 
• 3849-16-9 1r.3c-Dibenzyl-cyclohexanol-(2t) 
• 94961-40-7 (+/-)-trans-1.3-dibenzyl-cyclohexanone-⁽²⁾-semicarbazone 

Relevant academic research and scientific papers

Iron-Catalyzed Ligand Free α-Alkylation of Methylene Ketones and β-Alkylation of Secondary Alcohols Using Primary Alcohols

Herein, we demonstrate a general and broadly applicable catalytic cross coupling of methylene ketones and secondary alcohols with a series of primary alcohols to disubstituted branched ketones. A simple and nonprecious Fe2(CO)9 catalyst enables one-pot oxidations of both primary and secondary alcohols to a range of branched gem-bis(alkyl) ketones. A number of bond activations and formations selectively occurred in one pot to provide the ketone products. Coupling reactions can be performed in gram scale and successfully applied in the synthesis of an Alzehimer's drug. Alkylation of a steroid hormone can be achieved. A single catalyst enables sequential one-pot double alkylation to bis-hetero aryl ketones using two different alcohols. Preliminary mechanistic studies using an IR probe, deuterium labeling, and kinetic experiments established the participation of a borrowing-hydrogen process using Fe catalyst, and the reaction produces H2 and H2O as byproducts.

Piano-stool Ru (II) arene complexes that contain ethylenediamine and application in alpha-alkylation reaction of ketones with alcohols

A series of piano-stool Ru (II) complexes (Ru1–7) bearing ethylenediamine with aryl and aliphatic groups were prepared and fully characterized by 1H, 13C, 19F and 31P NMR spectroscopy, FT-IR and elemental analysis. The crystal structures of Ru2–4 and Ru7 were determined by X-ray crystallography. They were successfully applied to the alpha(α)-alkylation of aliphatic and aromatic ketones with alcohols via the borrowing hydrogen strategy in mild reaction conditions within a short time. The catalytic system has a broad substrate scope, which allows the synthesis of alpha alkylated ketones with excellent yields. The electronic and steric effects of complexes on catalytic activity were analysed. The influence of the carbon chain length of the ligand on the alpha-alkylation reaction of ketones was also investigated. The catalytic cycle was also examined by 1H-NMR spectroscopy in d8-toluene.

Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts

The catalytic alkylation of ketones with alcohols via the hydrogen borrowing methodology (HB) has the potential to be a highly efficient approach for forming new carbon-carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity. Other factors-base, base loading, solvent and reaction temperature-were also investigated to tune the selectivity further. The optimised conditions were used to demonstrate the scope of the reaction across 17 ketones and 14 alcohols containing a variety of functional groups. A series of mechanistic investigations were performed to probe the reasons behind the product selectivity, including kinetic and deuterium studies.

Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From Mechanistic Understanding to Application

Cyclopentadienone iron dicarbonyl complexes were applied in the alkylation of ketones with various aliphatic and aromatic ketones and alcohols via the borrowing hydrogen strategy in mild reaction conditions. DFT calculations and experimental works highlight the role of the transition metal Lewis pairs and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended the scope of substrates.

Clean borrowing hydrogen methodology using hydrotalcite supported copper catalyst

The catalytic activity of Mg-Al hydrotalcite supported copper catalyst was investigated for clean CC and CN bond forming reactions using alcohols as alkylating agent via borrowing hydrogen methodology. The catalyst showed excellent conversion of ketone and amine substrates (71-99%) to alkylated products with high selectivity in alkylation reactions.

α-Benzylation of Ketones by Reaction with Benzylamine. Regioselective Reduction of C-C Double Bonds in Cohjugated Enones

Prolonged reaction of some ketones with benzylamine at reflux converts them into α-benzyl derivatives by a route involving Aldol condensation of the related ketimine with benzaldimine followed by exclusive reduction of the resultant C-C double bond.Reduction does not occur when pure benzylamine is used under oxygen-free nitrogen, however the inclusion of a trace of benzaldehyde restores the efficiency of the reaction.Treatment of several ketones in this manner established the scope of the process.When the reaction was extended to the reduction of α,β-unsaturated enones again using benzylamine, reaction times were shorter and the product yield greater.The possibility that the reductive step was an intramolecular 1,5-hydrogen transfer was studied.

SELECTIVE REDUCTION OF C-C DOUBLE BONDS IN CONJUGATED ENONES BY BENZYLAMINE. A VARIANT OF THE SOMMELET REACTION

Prolonged reaction of some ketones with benzylamine at reflux converts them into α-benzyl derivatives by a route involving aldol condensation of the related ketimine with benzaldimine followed by exclusive reduction of the resultant C-C double bond by hydride transfer from benzylamine.This efficient procedure is a variant of the Sommelet reaction for the synthesis of aldehydes.

Selective Bulk-Hydrogenation of α,β Unsaturated Ketones to Ketones with Homogeneous Ir and Ru Catalysts

α,β Unsaturated ketones are selectively hydrogenated to ketones in homogeneous bulk-catalysis under mild conditions by iridium- and ruthenium complexes.The range of mean turnover is from 6 to 196 depending on substrate, catalyst and reaction conditions.Selectivity ketone/alcohol depends on the degree of conversion and exceeds 100 on conversion of 90percent. - Keywords: Catalysis, Homogeneous, Selective, Hydrogenation, Unsaturated Ketones