10264-57-0

Basic information

• Product Name: Cyclopentanone, 3-cyclohexyl-
• CAS NO: 10264-57-0
• Molecular Formula: C11H18O
• Molecular Weight: 166.263
• Mol File: 10264-57-0.mol

Chemical Properties

• CAS DataBase Reference: Cyclopentanone, 3-cyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanone, 3-cyclohexyl-(10264-57-0)
• EPA Substance Registry System: Cyclopentanone, 3-cyclohexyl-(10264-57-0)

Safety Data

• Hazardous Substances Data: 10264-57-0(Hazardous Substances Data)

Upstream product

• 930-30-3 cyclopent-2-enone 
• 110-82-7 cyclohexane 
• 931-50-0 cyclohexylmagnesium bromide 
• 108-85-0 1-bromocyclohexane 
• 15658-08-9 dicyclohexylzinc(II) 
• 626-62-0 Cyclohexyl iodide 
• 110604-56-3 1-diazo-5-cyclohexylpentan-2-one 
• 110-83-8 cyclohexene 
• 623-43-8 crotonic acid methyl ester 
• 2043-61-0 cyclohexanecarbaldehyde 
• 4441-63-8 4-cyclohexylbutanoic acid 
• 4441-67-2 4-cyclohexylbutyryl chloride 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 98-89-5 Cyclohexanecarboxylic acid 

Relevant articles and documents

Organocatalytic transfer hydrogenation of cyclic enones

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions. Copyright

Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes

(Chemical Equation Presented) With tungsten and lamp: Ketones were prepared by the photocatalytic generation of acyl radicals from aldehydes and trapping them with equimolar amounts of electrophilic alkenes. Photocatalysis with tetrabutylammonium decatungstate is effective also at low temperatures (-20 to -50°C), thus minimizing radical decarbonylation and allowing acylation by highly substituted aldehydes. EWG = electron-withdrawing group.

Photomediated synthesis of β-alkylketones from cycloalkanes

β-Cycloalkylketones are prepared through a photomediated radical addition reaction onto enones starting from the corresponding alkanes (i.e., cyclopentane, -hexane, -heptane, -dodecane and adamantane). The alkyl radicals are generated via hydrogen abstrac

Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis

A simple generation method of carbon radicals via 1e-oxidation of organotrifluoroborates and carboxylic acids by the action of an organophotoredox catalyst, 9-mesityl-10-methylacridinium perchlorate ([Acr+-Mes]ClO4), has been developed. This organophotocatalytic protocol is amenable to radical C-C bond formation with electron-deficient olefins.

Acridine Photocatalysis: Insights into the Mechanism and Development of a Dual-Catalytic Direct Decarboxylative Conjugate Addition

Conjugate addition is one of the most synthetically useful carbon-carbon bond-forming reactions; however, reactive carbon nucleophiles are typically required to effect the addition. Radical conjugate addition provides an avenue for replacing reactive nucleophiles with convenient radical precursors. Carboxylic acids can serve as simple and stable radical precursors by way of decarboxylation, but activation to reactive esters is typically necessary to facilitate the challenging decarboxylation. Here, we report a direct, dual-catalytic decarboxylative radical conjugate addition of a wide range of carboxylic acids that does not require acid preactivation and is enabled by the visible light-driven acridine photocatalysis interfaced with an efficient copper catalytic cycle. Mechanistic and computational studies provide insights into the roles of the ligands and metal species in the dual-catalytic process and the photocatalytic activity of substituted acridines.

Ultrasound in Organic Synthesis. 7. Preparation of Organozinc Reagents and Their Nickel-Catalyzed Reactions with α,β-Unsaturated Carbonyl Compounds

Diorganozinc compounds can be prepared with great ease and efficiency in a one-pot process, by sonication of lithium, an organic halide, and a zinc halide in THF or toluene mixtures.The reagents thus obtained give rise to clean and selective conjugate additions to α,β-unsaturated aldehydes and ketones in the presence of catalytic amounts of nickel acetylacetonate.

Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents

Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.

Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis

All-carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing α-quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent-allylic alcohol complex, which enables the first alkyl boronate addition and semi-pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an α-quaternary center in one step.

Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds

This works introduces hypervalent bis-catecholato silicon compounds as versatile sources of alkyl radicals upon visible-light photocatalysis. Using Ir[(dF(CF3)ppy)2(bpy)](PF6) (dF(CF3)ppy=2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy=bipyridine) as catalytic photooxidant, a series of alkyl radicals, including highly reactive primary ones can be generated and engaged in various intermolecular homolytic reactions. Based on cyclic voltammetry, Stern-Volmer studies, and supported by calculations, a mechanism involving a single-electron transfer from the silicate to the photoactivated iridium complex has been proposed. This oxidative photocatalyzed process can be efficiently merged with nickel-catalyzed Csp2-Csp3 cross-coupling reactions.

Catalytic enantioselective conjugate addition of Grignard reagents to cyclic enones using C1-1,1′-bisisoquinoline-based chiral ligands

New highly constrained chiral C1-1,1′-bisisoquinoline ligands were examined in the enantioselective conjugate addition of Grignard reagents to cyclohexenone and cyclopentenone. The desired 1,4-adducts were obtained in excellent yield and moderate enantiomeric excess (up to 35%). Copyright Taylor & Francis Group, LLC.