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Search Results (6)

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Keywords = cycloketone

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12 pages, 1615 KB  
Article
Synthesis of Thermal-Stable Aviation Fuel Additives with 4-Hydroxy-2-butanone and Cycloketones
by Anran Zhu, Zhufan Zou, Yu Cong, Yinghua Yin and Ning Li
Catalysts 2025, 15(9), 826; https://doi.org/10.3390/catal15090826 - 1 Sep 2025
Viewed by 1933
Abstract
A novel two-step strategy was developed for the efficient synthesis of decalin and octahydroindene from lignocellulose-derived platform compounds. In the first step, bicyclic intermediates were directly generated via a cascade dehydration/Robinson annulation of 4-hydroxy-2-butanone with cyclohexanone (or cyclopentanone). Among the evaluated catalysts, CaO [...] Read more.
A novel two-step strategy was developed for the efficient synthesis of decalin and octahydroindene from lignocellulose-derived platform compounds. In the first step, bicyclic intermediates were directly generated via a cascade dehydration/Robinson annulation of 4-hydroxy-2-butanone with cyclohexanone (or cyclopentanone). Among the evaluated catalysts, CaO demonstrated the highest activity and selectivity. Based on CO2-TPD results, the excellent performance of CaO can be rationalized by its proper basicity. In the second step, these intermediates were selectively hydrodeoxygenated to decalin (or octahydroindene) over Ni/H-ZSM-5 catalyst. Under the investigated reaction conditions, ~90% overall yields of decalin and octahydroindene were achieved. This work provides a viable strategy for the selective conversion of lignocellulose-derived platform compounds to the additives for improving the thermal stability of aviation fuel. Full article
(This article belongs to the Special Issue Back to the Future: Advances in Porous and Nanoscale Catalysts for Biomass Conversion to Value-Added Products)
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10 pages, 3405 KB  
Article
Green Synthesis of Spirooxindoles via Lipase-Catalyzed One-Pot Tandem Reaction in Aqueous Media
by Yong Tang, Ciduo Wang, Hanqing Xie, Yuelin Xu, Chunyu Wang, Chuang Du, Zhi Wang and Lei Wang
Catalysts 2023, 13(1), 143; https://doi.org/10.3390/catal13010143 - 7 Jan 2023
Cited by 11 | Viewed by 3608
Abstract
The development of non-natural enzymatic catalysis is important for multicomponent tandem organic transformations. However, the delicate acting environments of biological enzymes still present some challenges in the synthesis of spirooxindole skeleton via enzymatic catalysis. To address these issues, a lipase-catalyzed method was developed [...] Read more.
The development of non-natural enzymatic catalysis is important for multicomponent tandem organic transformations. However, the delicate acting environments of biological enzymes still present some challenges in the synthesis of spirooxindole skeleton via enzymatic catalysis. To address these issues, a lipase-catalyzed method was developed for the synthesis of spirooxindole frameworks. Using easily available isatins, cycloketones, and malononitriles as substrates, mild reaction conditions, and a reasonable reaction time, moderate to good yields (67–92%) and excellent functional group tolerance were accomplished via this protocol. The related mechanism explanation is also speculated in this paper. Full article
(This article belongs to the Special Issue Biocatalytic Cascade Reactions)
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18 pages, 13687 KB  
Review
The Baeyer–Villiger Oxidation of Cycloketones Using Hydrogen Peroxide as an Oxidant
by Qingguo Ma, Yanfeng Xue, Jiaming Guo and Xinhua Peng
Catalysts 2023, 13(1), 21; https://doi.org/10.3390/catal13010021 - 23 Dec 2022
Cited by 12 | Viewed by 8665
Abstract
Baeyer–Villiger oxidation can synthesize a series of esters or lactones that have essential application value but are difficult to be synthesized by other methods. Cycloketones can be oxidized to lactones using molecular oxygen, peroxy acids, or hydrogen peroxide as an oxidant. Hydrogen peroxide [...] Read more.
Baeyer–Villiger oxidation can synthesize a series of esters or lactones that have essential application value but are difficult to be synthesized by other methods. Cycloketones can be oxidized to lactones using molecular oxygen, peroxy acids, or hydrogen peroxide as an oxidant. Hydrogen peroxide is one of the environmental oxidants. Because of the weak oxidation ability of hydrogen peroxide, Bronsted acids and Lewis acids are used as catalysts to activate hydrogen peroxide or the carbonyl of ketones to increase the nucleophilic performance of hydrogen peroxide. The catalytic mechanisms of Bronsted acids and Lewis acids differ in the Baeyer–Villiger oxidation of cyclohexanone with an aqueous solution of hydrogen peroxide as an oxidant. Full article
(This article belongs to the Section Catalytic Reaction Engineering)
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16 pages, 4827 KB  
Article
Catalytic and Stoichiometric Baeyer–Villiger Oxidation Mediated by Nonheme Peroxo-Diiron(III), Acylperoxo, and Iodosylbenzene Iron(III) Intermediates
by Dóra Lakk-Bogáth, Miklós István Szávuly, Patrik Török and József Kaizer
Molecules 2022, 27(9), 2814; https://doi.org/10.3390/molecules27092814 - 28 Apr 2022
Cited by 9 | Viewed by 2742
Abstract
In this paper we describe a detailed mechanistic studies on the [FeII(PBO)2(CF3SO3)2] (1), [FeII(PBT)2(CF3SO3)2] (2), and [FeII(PBI) [...] Read more.
In this paper we describe a detailed mechanistic studies on the [FeII(PBO)2(CF3SO3)2] (1), [FeII(PBT)2(CF3SO3)2] (2), and [FeII(PBI)3](CF3SO3)2 (3)-catalyzed (PBO = 2-(2′-pyridyl)benzoxazole, PBT = 2-(2′-pyridyl)benzthiazole, PBI = 2-(2′-pyridyl)benzimidazole) Baeyer–Villiger oxidation of cycloketones by dioxygen with cooxidation of aldehydes and peroxycarboxylic acids, including the kinetics on the reactivity of (μ-1,2-peroxo)diiron(III), acylperoxo- and iodosylbenzene-iron(III) species as key intermediates. Full article
(This article belongs to the Section Inorganic Chemistry)
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11 pages, 1717 KB  
Article
Seven Conformations of the Macrocycle Cyclododecanone Unveiled by Microwave Spectroscopy
by Ecaterina Burevschi and M. Eugenia Sanz
Molecules 2021, 26(17), 5162; https://doi.org/10.3390/molecules26175162 - 26 Aug 2021
Cited by 8 | Viewed by 4385
Abstract
The physicochemical properties and reactivity of macrocycles are critically shaped by their conformations. In this work, we have identified seven conformations of the macrocyclic ketone cyclododecanone using chirped-pulse Fourier transform microwave spectroscopy in combination with ab initio and density functional theory calculations. Cyclododecanone [...] Read more.
The physicochemical properties and reactivity of macrocycles are critically shaped by their conformations. In this work, we have identified seven conformations of the macrocyclic ketone cyclododecanone using chirped-pulse Fourier transform microwave spectroscopy in combination with ab initio and density functional theory calculations. Cyclododecanone is strongly biased towards adopting a square configuration of the heavy atom framework featuring three C–C bonds per side. The substitution and effective structures of this conformation have been determined through the observation of its 13C isotopologues. The minimisation of transannular interactions and, to a lesser extent, HCCH eclipsed configurations drive conformational preferences. Our results contribute to a better understanding of the intrinsic forces mediating structural choices in macrocycles. Full article
(This article belongs to the Special Issue Exclusive Papers of the Editorial Board Members (EBMs) of the Physical Chemistry Section of Molecules)
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10 pages, 1909 KB  
Article
Organocatalysis for the Asymmetric Michael Addition of Cycloketones and α, β-Unsaturated Nitroalkenes
by Jae Ho Shim, Byung Kook Ahn, Ji Yeon Lee, Hyeon Soo Kim and Deok-Chan Ha
Catalysts 2021, 11(8), 1004; https://doi.org/10.3390/catal11081004 - 20 Aug 2021
Cited by 9 | Viewed by 7280
Abstract
Michael addition is one of the most important carbon–carbon bond formation reactions. In this study, an (R, R)-1,2-diphenylethylenediamine (DPEN)-based thiourea organocatalyst was applied to the asymmetric Michael addition of nitroalkenes and cycloketones to produce a chiral product. The primary amine [...] Read more.
Michael addition is one of the most important carbon–carbon bond formation reactions. In this study, an (R, R)-1,2-diphenylethylenediamine (DPEN)-based thiourea organocatalyst was applied to the asymmetric Michael addition of nitroalkenes and cycloketones to produce a chiral product. The primary amine moiety in DPEN reacts with the ketone to form an enamine and is activated through the hydrogen bond formation between the nitro group in the α, β-unsaturated nitroalkene and thiourea. Here, the aim was to obtain an asymmetric Michael product through the 1,4-addition of the enamine to an alkene to form a new carbon–carbon bond. As a result, the primary amine of the chiral diamine was converted into an enamine. The reaction proceeded with a relatively high level of enantioselectivity achieved using double activation through the hydrogen bonding of the nitro group and thiourea. Michael products with high levels of enantioselectivity (76–99% syn ee) and diastereoselectivity (syn/anti = 9/1) were obtained with yields in the range of 88–99% depending on the ketone. Full article
(This article belongs to the Special Issue Organocatalysis: Mechanistic Investigations, Design, and Applications)
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