Summary: Alicyclic hydrocarbons in which three or more of the carbon atoms in each molecule are united in a ring structure and each of the ring carbon atoms is joined to two hydrogen atoms or alkyl groups. The simplest members are cyclopropane (C3H6), cyclobutane (C4H8), cyclohexane (C6H12), and derivatives of these such as methylcyclohexane (C6H11CH3). (From Sax, et al., Hawley's Condensed Chemical Dictionary, 11th ed)

Top Publications

  1. Tummatorn J, Batsomboon P, Clark R, Alabugin I, Dudley G. Strain-promoted azide-alkyne cycloadditions of benzocyclononynes. J Org Chem. 2012;77:2093-7 pubmed publisher
    ..g., 1) provide valuable insight into the design of new cycloalkynes for strain-promoted azide-alkyne cycloaddition (SPAAC) couplings for applications in which side reactions and decomposition of the reagent must be kept to a minimum. ..
  2. Peter S, Kinne M, Ullrich R, Kayser G, Hofrichter M. Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase. Enzyme Microb Technol. 2013;52:370-6 pubmed publisher
    ..Stable and versatile peroxygenases as that of A. aegerita may form a promising biocatalytic platform for the development of such enzyme-based syntheses. ..
  3. Zhang J, Ma K, Li Y, Zhang Y, Wu L, Li X, et al. [Study on therapeutic effects of series of muskone on myocardial infarction canines]. Zhongguo Zhong Yao Za Zhi. 2006;31:1702-5 pubmed
    ..The series of Muskone has significant therapeutic effect on myocardial infarction. ..
  4. Lee K, Hoveyda A. Monodentate non-C(2)-symmetric chiral N-heterocyclic carbene complexes for enantioselective synthesis. Cu-catalyzed conjugate additions of aryl- and alkenylsilylfluorides to cyclic enones. J Org Chem. 2009;74:4455-62 pubmed publisher
    ..Toward this end, nearly 20 new chiral monodentate imidazolinium salts, most of which are non-C(2)-symmetric, have been prepared and fully characterized and their ability to serve as catalysts in the ECA reactions has been investigated. ..
  5. Okagbare P, Emory J, Datta P, Goettert J, Soper S. Fabrication of a cyclic olefin copolymer planar waveguide embedded in a multi-channel poly(methyl methacrylate) fluidic chip for evanescence excitation. Lab Chip. 2010;10:66-73 pubmed publisher
    ..1 x 10(-20) mol at a signal-to-noise ratio of 2. The waveguide was simple to manufacture and could be scaled to illuminate much higher channel numbers making it appropriate for high-throughput measurements using evanescent excitation. ..
  6. Mampreian D, Hoveyda A. Efficient Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to aromatic and aliphatic acyclic nitroalkenes. Org Lett. 2004;6:2829-32 pubmed
    ..C(6)H(6). Nitroalkenes bearing aromatic as well as aliphatic substituents readily undergo asymmetric additions. [reaction: see text] ..
  7. Tsukamoto H, Matsumoto T, Kondo Y. Microwave-assisted palladium(0)-catalyzed alkylative cyclization of allenyl aldehydes leading to 3-substituted 3-cycloalken-1-ols. J Am Chem Soc. 2008;130:388-9 pubmed
  8. Su D, Wang X, Shao C, Xu J, Zhu R, Hu Y. Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition. J Org Chem. 2011;76:188-94 pubmed publisher
    ..Thus, by using Fukuyama's oxime synthesis, a general method was developed for highly efficient conversion of 3-(N,N-dialkylamino)propanols into 3-(N,N-dialkylamino)propanal oximes without using the corresponding aldehydes. ..
  9. Fuchiwaki Y, Saito M, Wakida S, Tamiya E, Nagai H. A practical liquid plug flow-through polymerase chain-reaction system based on a heat-resistant resin chip. Anal Sci. 2011;27:225-30 pubmed
    ..Thus, this liquid plug flow-through PCR system, based on our novel PCR chip, excelled in a practical applications compared to other devices. ..

More Information


  1. Jana D, Wodrich M, Corminboeuf C. Structure-correlation principles connecting ground state properties and reaction barrier heights for the Cope rearrangement of semibullvalenes. J Org Chem. 2012;77:2548-52 pubmed publisher
    ..Examination of electron density distribution, geometrical parameters, and J-coupling constant differences between canonical and Lewis structures deliver quantitative evidence for the structure-correlation principle. ..
  2. Zhang M, Tang W. Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition. Org Lett. 2012;14:3756-9 pubmed publisher
    ..A pentasubstituted cyclopropane was prepared successfully by a Rh(II)-catalyzed intramolecular cyclopropanation of alkenes with chlorodiazoacetates. ..
  3. Kerber W, Koh J, GAGNE M. Platinum(II)-catalyzed 1,6-diene cycloisomerizations: turnover in the absence of beta-hydride elimination. Org Lett. 2004;6:3013-5 pubmed
    ..PPP ligands lead to cyclopropane products, while PNP ligands provide cyclohexene products; mechanistic issues are also discussed. ..
  4. Zou L, Lin J, Hu H, Wang Y, Wang P, Zhao G, et al. [Effect of borneol on intestinal absorption of muscone in rats]. Zhongguo Zhong Yao Za Zhi. 2012;37:3490-3 pubmed
    ..05); and so did in jejunum (Ka, P < 0.05; T1/2, P < 0.05); in ileum, there was no significant statistical difference between LBMG and MG. Borneol can promote the intestinal absorption of muscone in rats to some extent. ..
  5. Suárez Moreno G, González Zamora E, Méndez F. Oxazole as an electron-deficient diene in the Diels-Alder reaction. Org Lett. 2011;13:6358-61 pubmed publisher
    ..The efficacy consists of stabilizing the transition state, lowering the activation barrier and the HOMO(dienophile)-LUMO(diene) gap, and increasing the reaction exothermicity. ..
  6. Fuchiwaki Y, Nagai H, Saito M, Tamiya E. Ultra-rapid flow-through polymerase chain reaction microfluidics using vapor pressure. Biosens Bioelectron. 2011;27:88-94 pubmed publisher
    ..The PCR chip had sufficient sensitivity for anthrax identification. The fastest time from aerosol sampling to detection was theoretically estimated as 8 min. ..
  7. Wei G, Chen D, Lai X, Liu D, Deng R, Zhou J, et al. Muscone exerts neuroprotection in an experimental model of stroke via inhibition of the fas pathway. Nat Prod Commun. 2012;7:1069-74 pubmed
    ..These findings suggest a potential therapeutic role for muscone in the treatment of stroke. ..
  8. Sung D, Yang S, Park J, Jon S. High-density immobilization of antibodies onto nanobead-coated cyclic olefin copolymer plastic surfaces for application as a sensitive immunoassay chip. Biomed Microdevices. 2013;15:691-698 pubmed publisher
    ..1 ng/mL versus 10 ng/mL), indicating the potential value of the proposed immunoassay system in plastic-based portable biochip applications. ..
  9. Murahashi T, Inoue R, Usui K, Ogoshi S. Square tetrapalladium sheet sandwich complexes: cyclononatetraenyl as a versatile face-capping ligand. J Am Chem Soc. 2009;131:9888-9 pubmed publisher
    ..The coordinative unsaturation of the complex was revealed by phosphine titration experiments. ..
  10. Peng X, Zhao L, Du G, Wei X, Guo J, Wang X, et al. Charge tunable zwitterionic polyampholyte layers formed in cyclic olefin copolymer microchannels through photochemical graft polymerization. ACS Appl Mater Interfaces. 2013;5:1017-23 pubmed publisher
    ..The uniformity of the modified layers was verified through a comparison of electrophoresis inside the modified and native microchannels. A whole blood coagulation time measurement was performed to show its applicability. ..
  11. Wei X, Sun P, Yang S, Zhao L, Wu J, Li F, et al. Microchip electrophoresis with background electrolyte containing polyacrylic acid and high content organic solvent in cyclic olefin copolymer microchips for easily adsorbed dyes. J Chromatogr A. 2016;1457:144-50 pubmed publisher
    ..The limit of detection (S/N=3) was 0.1nmol/L for Rh6G. The proposed technique was applied in the determination of both Rh6G and RhB in chilli powder and lipstick samples with satisfactory recoveries of 81.3-103.7%. ..
  12. Balaban A, Mills D, Kodali V, Basak S. Complexity of chemical graphs in terms of size, branching, and cyclicity. SAR QSAR Environ Res. 2006;17:429-50 pubmed
    ..This comparison involved all possible chemical graphs (i.e. connected planar graphs with vertex degrees not higher than four) with four through six vertices, and all possible alkanes with four through nine carbon atoms. ..
  13. Choi T, Rutenberg I, Grubbs R. Synthesis of A,B-alternating copolymers by ring-opening-insertion-metathesis polymerization. Angew Chem Int Ed Engl. 2002;41:3839-41 pubmed
  14. Knopff O, Kuhne J, Fehr C. Enantioselective intramolecular aldol addition/dehydration reaction of a macrocyclic diketone: synthesis of the musk odorants (R)-muscone and (R,Z)-5-muscenone. Angew Chem Int Ed Engl. 2007;46:1307-10 pubmed
  15. Sidduri A, Tilley J, Hull K, Lou J, Kaplan G, Sheffron A, et al. N-Cycloalkanoyl-L-phenylalanine derivatives as VCAM/VLA-4 antagonists. Bioorg Med Chem Lett. 2002;12:2475-8 pubmed
    ..The data are consistent with a model of these compounds in which these alkanoylphenylalanines reside in a compact gauche (-) bioactive conformation. ..
  16. Cordero Vargas A, Quiclet Sire B, Zard S. Model studies towards the synthesis of gilvocarcin M. Org Biomol Chem. 2005;3:4432-43 pubmed
    ..In model studies towards the synthesis of gilvocarcin M, a convergent, xanthate-based free-radical strategy was tested in order to construct the key aromatic ring attached to the sugar unit. ..
  17. Gubala V, Gandhiraman R, Volcke C, Doyle C, Coyle C, James B, et al. Functionalization of cycloolefin polymer surfaces by plasma-enhanced chemical vapour deposition: comprehensive characterization and analysis of the contact surface and the bulk of aminosiloxane coatings. Analyst. 2010;135:1375-81 pubmed publisher
    ..The use of the techniques described in this article is aimed to set new standards for the characterization and analysis of the substrate surface of the future diagnostic devices. ..
  18. Staben S, Linghu X, Toste F. Enantioselective synthesis of gamma-hydroxyenones by chiral base-catalyzed Kornblum DeLaMare rearrangement. J Am Chem Soc. 2006;128:12658-9 pubmed
    ..Thus, enantioenriched 4-hydroxyenones are prepared from dienes by a two-step sequence involving photochemical dioxygenation and chiral base-catalyzed desymmetrization of the resulting endoperoxides. ..
  19. Tsvetkov N, Bayir A, Schneider S, Brewer M. A ring fragmentation approach to medium-sized cyclic 2-alkynones. Org Lett. 2012;14:264-7 pubmed publisher
    ..This method provides good to excellent yields of 10-, 11-, and 12-membered alkynone products. ..
  20. Rahman A, Ali R, Jahng Y, Kadi A. A facile solvent free Claisen-Schmidt reaction: synthesis of ?,?'-bis-(substituted-benzylidene)cycloalkanones and ?,?'-bis-(substituted-alkylidene)cycloalkanones. Molecules. 2012;17:571-83 pubmed publisher
    ..Using the same method, we could synthesize the corresponding bis-benzylidene- and mono-benzylideneacetone separately in 98% and 96% yields, respectively...
  21. Joubert J, Geldenhuys W, Van der Schyf C, Oliver D, Kruger H, Govender T, et al. Polycyclic cage structures as lipophilic scaffolds for neuroactive drugs. ChemMedChem. 2012;7:375-84 pubmed publisher
  22. Karabunarliev S, Dimitrov S, Pavlov T, Nedelcheva D, Mekenyan O. Simulation of chemical metabolism for fate and hazard assessment. IV. Computer-based derivation of metabolic simulators from documented metabolism maps. SAR QSAR Environ Res. 2012;23:371-87 pubmed publisher
    ..The approach and its results are illustrated for a metabolic map collection of 15 cycloalkanes. ..
  23. Elgemeie G, El Enany M, Ismail M, Ahmed E. Nucleic acid components and their analogues: a novel and efficient method for the synthesis of a new class of bipyridyl and biheterocyclic-nitrogen thioglycosides from pyridine-2(1H)-thiones. Nucleosides Nucleotides Nucleic Acids. 2002;21:477-93 pubmed
  24. Dounay A, Humphreys P, Overman L, Wrobleski A. Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization. J Am Chem Soc. 2008;130:5368-77 pubmed publisher
    ..A distinctive feature of this sequence is the use of palladium-catalyzed reactions to form all carbon-carbon bonds in the transformation of these simple precursors to (+)-minfiensine...
  25. Ladner Y, Crétier G, Faure K. Electrochromatography on acrylate-based monolith in cyclic olefin copolymer microchip: a cost-effective and easy-to-use technology. Electrophoresis. 2012;33:3087-94 pubmed publisher
    ..The detection limit of fluoranthene is decreased down to less than 1 ppb with a preconcentration of 4.5 h on the HA-filled PEGMA functionalized COC microchip. ..
  26. Wang Q, Zhang Y, Ding H, Wu J, Wang L, Zhou L, et al. The use of ethylene glycol solution as the running buffer for highly efficient microchip-based electrophoresis in unmodified cyclic olefin copolymer microchips. J Chromatogr A. 2011;1218:9422-7 pubmed publisher
    ..4% and 0.7%, respectively. Furthermore, the system was successfully applied to elucidate these five amino acids in human saliva. ..
  27. Mizuno N, Yamaguchi K. Polyoxometalate catalysts: toward the development of green H2O2-based epoxidation systems. Chem Rec. 2006;6:12-22 pubmed
    ..Furthermore, the heterogenization of the mentioned polyoxometalates can be achieved by using ionic liquid-modified SiO(2) as a support without loss of catalytic performance. ..
  28. Doerr A. A synthetic classic reinvented. Nat Methods. 2006;3:77 pubmed
  29. Kumar P, Li P, Korboukh I, Wang T, Yennawar H, Weinreb S. Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems. J Org Chem. 2011;76:2094-101 pubmed publisher
    ..A sulfonamide anion has also been found to be an effective nucleophile in this type of reaction, leading to formation of a 6-azabicyclo[3.2.1]octane. ..
  30. Wu X, Lu Y, Hirao H, Zhou J. Achieving vinylic selectivity in Mizoroki-Heck reaction of cyclic olefins. Chemistry. 2013;19:6014-20 pubmed publisher
    ..The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. ..
  31. Jeon J, Chung S, Kamm R, Charest J. Hot embossing for fabrication of a microfluidic 3D cell culture platform. Biomed Microdevices. 2011;13:325-33 pubmed publisher
    ..The results demonstrate a methodology to transition microfluidic devices for 3D cell culture from scientific research to high-volume applications with broad clinical impact. ..
  32. Cook C, Barrett A, Roach E, Bowman J, Picker M. Sex-related differences in the antinociceptive effects of opioids: importance of rat genotype, nociceptive stimulus intensity, and efficacy at the mu opioid receptor. Psychopharmacology (Berl). 2000;150:430-42 pubmed
  33. Sirjean B, Glaude P, Ruiz Lòpez M, Fournet R. Theoretical kinetic study of the reactions of cycloalkylperoxy radicals. J Phys Chem A. 2009;113:6924-35 pubmed publisher
  34. Raj J, Herzog G, Manning M, Volcke C, MacCraith B, Ballantyne S, et al. Surface immobilisation of antibody on cyclic olefin copolymer for sandwich immunoassay. Biosens Bioelectron. 2009;24:2654-8 pubmed publisher
    ..Non-specific binding effects were also assessed. The method and supporting data demonstrate that simple approaches to surface functionalisation can be adapted to plastic-based devices. ..
  35. Jahn U, Galano J, Durand T. Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids. Angew Chem Int Ed Engl. 2008;47:5894-955 pubmed publisher
    ..In a relatively short time, the structural variety, properties, and applications of the autoxidatively formed cyclic PUFA derivatives have been uncovered. ..
  36. Paquette L, Dong S, Parker G. Pestalotiopsin A. Side chain installation and exhaustive probing of olefin metathesis as a possible tool for elaborating the cyclononene ring. J Org Chem. 2007;72:7135-47 pubmed
    ..Cross-metathesis experiments involving 59 and 65 with the functionalized heptene 60 revealed a marked difference in the inability to engage interaction with the ruthenium catalyst. This awkwardness could not be skirted. ..
  37. Armstrong J, Greenberg S. Evaluation of extended-life pheromone formulations used with and without dichlorvos for boll weevil (Coleoptera: Curculionidae) trapping. J Econ Entomol. 2008;101:399-403 pubmed
  38. Ross A, Townsend S, Danishefsky S. Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns. J Org Chem. 2013;78:204-10 pubmed publisher
    ..A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cyclopropyl functional handles is described. ..
  39. Lee K, Lee T, Jeong S, Choi H, Heo N, Park J, et al. Development of a plastic-based microfluidic immunosensor chip for detection of H1N1 influenza. Sensors (Basel). 2012;12:10810-9 pubmed publisher
    ..This protocol could be applied to the diagnosis of other infectious diseases in a microfluidic device. ..
  40. Wu Z, Lifka J, Ondruschka B. Benzene formation during aquasonolysis of selected cyclic C6Hx hydrocarbons. Ultrason Sonochem. 2005;12:133-6 pubmed
    ..During the aquasonolysis of 1,3-cyclohexadiene and cyclohexene, other C6 species except benzene were also found. It was suggested that benzene could directly be generated by formal dehydrogenation of cyclic C6Hx hydrocarbons. ..
  41. Huang S, Lohman J, Huang T, Shen B. A new member of the 4-methylideneimidazole-5-one-containing aminomutase family from the enediyne kedarcidin biosynthetic pathway. Proc Natl Acad Sci U S A. 2013;110:8069-74 pubmed publisher
  42. Trost B, Rudd M. Ruthenium-catalyzed cycloisomerizations of diynols. J Am Chem Soc. 2005;127:4763-76 pubmed
    ..Primary diynols undergo a cycloisomerization as well as a hydrative cyclization process. The utility of primary diynol cycloisomerization is demonstrated in a synthesis of (+)-alpha-kainic acid...
  43. Pellizzari E, Clayton C, Rodes C, Mason R, Piper L, Fort B, et al. Particulate matter and manganese exposures in Indianapolis, Indiana. J Expo Anal Environ Epidemiol. 2001;11:423-40 pubmed
    ..5) Mn concentrations. Comparisons of the particulate distributions between PTEAM (Riverside, CA) and the Indianapolis and Toronto studies were also made. ..
  44. Liu J, Chen C, Yang S, Chang C, DeVoe D. Mixed-mode electrokinetic and chromatographic peptide separations in a microvalve-integrated polymer chip. Lab Chip. 2010;10:2122-9 pubmed publisher
    ..The reusable system is shown to provide efficient 2-D separations together with facile interfacing with MALDI-MS, suggesting a new path towards effective peptide analysis from complex samples. ..
  45. Tandon V, Kirby B. Ambient pressure effects on the electrokinetic potential of Zeonor-water interfaces. J Colloid Interface Sci. 2011;361:381-7 pubmed publisher
    ..This can be described as a type of hysteresis of the electrokinetic potential with dissolved gas concentration. No time or pressure dependence was observed for the electrokinetic potential of hydrophilic (silica) substrates. ..
  46. Lehmann J, Alzieu T, Martin R, Britton R. The Kondrat'eva reaction in flow: direct access to annulated pyridines. Org Lett. 2013;15:3550-3 pubmed publisher
    ..Annulated pyridines obtained by this one-step process are valuable scaffolds for medicinal chemistry. ..
  47. Grunewald G, Grindel J, Patil P, Salman K. Importance of the aromatic ring in adrenergic amines. 2. Synthesis and adrenergic activity of some nonaromatic six- and eight-membered ring analogs of beta-phenylethanolamine. J Med Chem. 1976;19:10-6 pubmed
  48. Carrillo Marquez T, Caggiano L, Jackson R, Grabowska U, Rae A, Tozer M. New routes to beta-cycloalkylalanine derivatives using serine-derived organozinc reagents. Org Biomol Chem. 2005;3:4117-23 pubmed
    ..The corresponding cyclopentyl derivative may be prepared by reaction of the same zinc-copper reagent 2 with diethyl geranylphosphate, followed by ring-closing metathesis and hydrogenation. ..
  49. Gu P, Liu K, Chen H, Nishida T, Fan Z. Chemical-assisted bonding of thermoplastics/elastomer for fabricating microfluidic valves. Anal Chem. 2011;83:446-52 pubmed publisher
    ..The valve-containing devices withstood 100 psi (?689 KPa) without delamination. Further, we integrated such valve arrays in a device for protein separation and demonstrated isoelectric focusing in the presence of valves. ..
  50. Tuttle J, Ouellet S, MacMillan D. Organocatalytic transfer hydrogenation of cyclic enones. J Am Chem Soc. 2006;128:12662-3 pubmed
    ..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. ..
  51. Chini M, Riccio R, Bifulco G. DFT/NMR integrated approach: a valid support to the total synthesis of chiral molecules. Magn Reson Chem. 2008;46:962-8 pubmed publisher
  52. Wang M, Wong M, Che C. Gold(I)-catalyzed intermolecular hydroarylation of alkenes with indoles under thermal and microwave-assisted conditions. Chemistry. 2008;14:8353-64 pubmed publisher
    ..On the basis of deuterium-labeling experiments, a reaction mechanism involving nucleophilic attack of Au(I)-coordinated alkenes by indoles is proposed. ..
  53. Young I, Kerr M. Total synthesis of (+)-nakadomarin A. J Am Chem Soc. 2007;129:1465-9 pubmed
    ..Overall, the synthesis required 23 linear steps from the cyclopropane, which in turn is available (six steps) in optically pure form from commercially available d-mannitol. ..