712-50-5

Usage

Uses

Used in Research and Development:
Benzoylcyclohexane is used as a research compound for investigating the crosslinked cyclohexyl phenyl compounds under thermal and aquathermal conditions. This helps in understanding the molecular changes and their effects on the properties of the compounds.
Used in Photochemistry:
In the field of photochemistry, benzoylcyclohexane is used as a study subject to examine the effects of molecular changes in the benzophenone molecule on phototoxic behavior. This research can contribute to the development of new compounds with specific phototoxic properties for various applications, such as in the pharmaceutical or chemical industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 4792, 1985 DOI: 10.1021/ja00302a039The Journal of Organic Chemistry, 58, p. 2483, 1993 DOI: 10.1021/jo00061a023Tetrahedron Letters, 28, p. 6229, 1987 DOI: 10.1016/S0040-4039(00)61854-3

Biochem/physiol Actions

Cyclohexyl phenyl ketone induces photohaemolysis after exposure to ultraviolet A-rich irradiation in human erythrocytes.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES

InChI:InChI=1/C13H16O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8,12H,2,5-6,9-10H2

Upstream product

• 4848-85-5 Dicyclohexylquecksilber 
• 98-88-4 benzoyl chloride 
• 110-83-8 cyclohexene 
• 100-47-0 benzonitrile 
• 931-50-0 cyclohexylmagnesium bromide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 71-43-2 benzene 
• 766-66-5 2-chlorocycloheptanone 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 626-62-0 Cyclohexyl iodide 
• 57848-81-4 2-cyclohexyl-2-phenyl-benzo[1,3]oxathiole 
• 17040-65-2 1-cyclohexenyl(phenyl)methanone 
• 3893-23-0 cyclohexyl phenyl acetonitrile 

Downstream Products

• 63334-00-9 1-cyclohexyl-1-phenyl-2-[2]pyridyl-ethanol 
• 102465-67-8 1-cyclohexyl-4-diethylamino-1-phenyl-but-2-yn-1-ol 
• 3954-12-9 phenyl cyclohexanecarboxylate 
• 2412-73-9 benzoic acid cyclohexyl ester 
• 945-49-3 cyclohexylphenylmethanol 
• 87839-87-0 α,α-Dicyclohexylbenzolmethanol 
• 7468-34-0 5-bromomethyl-2-cyclohexyl-5-methyl-2-phenyl-[1,3]dioxane 
• 4404-61-9 cyclohexyldiphenylmethanol 
• 827-52-1 1-phenyl-1-cyclohexane 
• 4410-75-7 (cyclohexylmethyl)benzene 
• 7500-66-5 (1-bromocyclohexyl)(phenyl)methanone 
• 2891-42-1 (1-ethyl-cyclohexyl)-phenyl ketone 
• 834-41-3 1-cyclohexyl-1-hydroxy-1-phenyl-2-propyne 
• 1135-71-3 (1-chlorocyclohexyl)(phenyl)methanone 

Relevant academic research and scientific papers

Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides

We report the Pd-catalyzed Suzuki-Miyaura cross-coupling of aliphatic amides. Although tremendous advances have been made in the cross-coupling of aromatic amides, C-C bond formation from aliphatic amides by selective N-C(O) cleavage has remained a major challenge. This longstanding problem in Pd catalysis has been addressed herein by a combination of (1) the discovery of N,N-pym/Boc amides as a class of readily accessible amide-based reagents for cross-coupling and (2) steric tuning of well-defined Pd(II)-NHC catalysts for cross-coupling. The methodology is effective for the cross-coupling of an array of 3°, 2°, and 1° aliphatic amide derivatives. The catalyst system is user-friendly, since the catalysts are readily available and are air- and bench-stable. Mechanistic studies strongly support an amide bond twist and external nN → π*C═O/Ar delocalization as a unified enabling feature of N,N-pym/Boc amides in selective N-C(O) bond activation. The method provides a rare example of Pd-NHC-catalyzed cross-coupling of aliphatic acyl amide electrophiles.

Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process

A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety of ketones as major products. The reaction proceeds at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibits several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). (Figure presented.).

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Rapid and Direct Photocatalytic C(sp3)?H Acylation and Arylation in Flow

Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)?C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.

Preparation method of photoinitiator

The invention discloses a preparation method of a photoinitiator. The preparation method comprises the following steps: acid chloride required for Fries reaction, aluminum trichloride and a solvent are mixed and then subjected to a Fourier reaction with benzene. Fries reaction intermediate purification method The Fourier reaction intermediate is mixed with chlorine for chlorination reaction, and the product of the chlorination reaction is subjected to gas-liquid separation to separate the gas. Reaction Section Step and The product purification step results in a photoinitiator finished product. To the technical scheme of the invention, the advantages of the traditional process of producing the photoinitiator are combined with the characteristics of the microchannel reactor to realize continuous preparation, the productivity can be improved, the production risk is reduced, the manpower and equipment investment are reduced, and the cost is further reduced.

o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

Ano-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation. The characteristics of thiso-QM enable the operation of dehydridative catalysis in the oxidation of benzylic secondary alcohols under aerobic photoirradiation conditions. An experimental analysis and density functional theory calculations provide mechanistic insights; the ground-state zwitterionic intermediate abstracts a hydride and proton simultaneously, and the active oxygen species facilitate catalyst regeneration.

Catalytic alcohol oxidation using cationic Schiff base manganeseIII complexes with flexible diamino bridge

Four Schiff base manganese(III) complexes with derivatives of [(R,R)-N,N’-bis(salicy1idene)-1,2-cyclohexanediaminato)] including substituents on salicylaldehyde such as 3-methoxy, 3,5-di-tert-butyl and 3,5-chloro were synthesized and characterized using a combination of IR, UV–Vis, and HR ESI-MS techniques. The catalytic activity of these complexes was tested in the oxidation of 1-phenylethanol to acetophenone, revealing very good performances for all of the four manganese complexes. The catalytic reactions were carried out in the presence of tert-butyl hydroperoxide (TBHP) as oxidant and imidazole as co-catalyst. Complex Mn-4, bearing electron withdrawing [(R,R)-N,N’-bis(3,5-di-chloro-salicylidene)-1,2-cyclohexanediaminato)] ligand was found to be the most stable of the tested Mn(III) complexes and was selected for the oxidation of several primary and secondary alcohols.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.