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Journal articles on the topic 'Cyclohexenones'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Okoth, Dorothy A., and Neil A. Koorbanally. "Cardanols, Long Chain Cyclohexenones and Cyclohexenols from Lannea schimperi (Anacardiaceae)." Natural Product Communications 10, no. 1 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000126.

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Alkenyl cyclohexenones (1a-d), alkenyl cyclohexenols (2a-c and 3b-d) and cardanols (4a-d) were isolated from the stem bark and root of Lannea schimperi. The alkenyl cyclohexenones (1a and 1d) and cardanols (4a and 4d) have side chains which have not been reported previously, in combination with the core skeletal structures. In addition, compounds 2a-c and 3b-d are all new cyclohexenols. Also isolated were the triterpenes, taraxerone and taraxerol, and sitosterol. The suite of compounds isolated (cyclohexenones and cyclohexenols) make up a nice biosynthetic pathway to the cardanols. The 5-[alke

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2

Hylden, Anne T., Eric J. Uzelac, Zeljko Ostojic, et al. "Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones." Beilstein Journal of Organic Chemistry 7 (September 23, 2011): 1323–26. http://dx.doi.org/10.3762/bjoc.7.155.

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The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

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3

Davis, BR, MG Hinds, and SJ Johnson. "Diterpene Synthesis. III. Acid-Catalyzed Cyclization of Methoxyphenylethyltrimethyl-Cyclohexanols, Cyclohexenols and Cyclohexenones." Australian Journal of Chemistry 38, no. 12 (1985): 1815. http://dx.doi.org/10.1071/ch9851815.

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Cyclization of the methoxyphenylethyltrimethylcyclohexanols (3), (4) and (5), the cyclohexenols (6) and (7) and the cyclohexenones (20) and (21), in the presence of a variety of acids, has been studied and the products analysed by chromatographic and spectroscopic techniques. Both cis - and trans-podocarpa-8,11,13-trienes are formed, along with the rearranged compounds (16), (17) and (30). These results parallel our earlier findings and contrast with some reports in the literature.

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4

Schuster, David I., Jie-Min Yang, Jan Woning, Timothy A. Rhodes, and Anton W. Jensen. "Mechanism of acid-catalyzed photoaddition of methanol to 3-alkyl2-cyclohexenones." Canadian Journal of Chemistry 73, no. 11 (1995): 2004–10. http://dx.doi.org/10.1139/v95-247.

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Contrary to a previous report, it is concluded that formation of methanol adducts to 3-methyl-2-cyclohexenones and of deconjugated enones on irradiation of the enones in acidified solutions proceeds via protonation of the intermediate enone π,π* triplet excited state and not by protonation of a relatively long-lived ground state trans-cyclohexenone. A rate constant for protonation of the triplet state of 3-methyl-2-cyclohexenone by sulfuric acid of 1.7 × 109 M−1 s−1 was determined by laser flash photolysis in ethyl acetate. Based on quantum efficiencies of product formation, a rate constant of

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5

Weir, D., J. C. Scaiano, and D. I. Schuster. "A reinvestigation of the interaction between triplet states of cyclohexenones and amines." Canadian Journal of Chemistry 66, no. 10 (1988): 2595–600. http://dx.doi.org/10.1139/v88-407.

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Laser flash photolysis studies lead to the conclusion that the short-lived triplet states of cyclohexenones are readily quenched by amines. For example, in the case of 2-cyclohexen-1-one (1) its triplet state (τT = 40 ns in acetonitrile) is quenched by triethylamine with a rate constant of (9.0 ± 0.8) × 107 M−1 s−1. Cyclohexenone triplets are also quenched efficiently by DABCO and by triphenylamine leading to the formation of the corresponding amine radical cations. The new evidence reported rules out the involvement of long-lived detectable exciplexes.

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6

Helmchen, G., G. Franck, and K. Brödner. "Enantioselective Synthesis of Cyclohexenones." Synfacts 2010, no. 10 (2010): 1166. http://dx.doi.org/10.1055/s-0030-1258649.

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7

Weldetsadik, Ermias Tamiru, Na Li, Jingjuan Li, Jiahuan Shang, Hongtao Zhu, and Yingjun Zhang. "Undescribed Cyclohexene and Benzofuran Alkenyl Derivatives from Choerospondias axillaris, a Potential Hypoglycemic Fruit." Foods 13, no. 10 (2024): 1495. http://dx.doi.org/10.3390/foods13101495.

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The fruit of Choerospondias axillaris (Anacardiaceae), known as south wild jujube in China, has been consumed widely in several regions of the world to produce fruit pastille and leathers, juice, jam, and candy. A comprehensive chemical study on the fresh fruits led to the isolation and identification of 18 compounds, including 7 new (1–7) and 11 known (8–18) comprised of 5 alkenyl (cyclohexenols and cyclohexenones) derivatives (1–5), 3 benzofuran derivatives (6–8), 6 flavonoids (9–14) and 4 lignans (15–18). Their structures were elucidated by extensive spectroscopic analysis. The known lignan

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8

VERHE, R. "ChemInform Abstract: 3-Isobutoxy-2-cyclohexenone: A Versatile Synthon for the Regiospecific Alkylation of Cyclohexenones." ChemInform 24, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199352309.

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9

Clot-Almenara, Lidia, Carles Rodríguez-Escrich, and Miquel A. Pericàs. "Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst." RSC Advances 8, no. 13 (2018): 6910–14. http://dx.doi.org/10.1039/c7ra13471a.

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10

Samser, Shaikh, Priyabrata Biswal, Sushanta Kumar Meher, and Krishnan Venkatasubbaiah. "Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones." Organic & Biomolecular Chemistry 19, no. 6 (2021): 1386–94. http://dx.doi.org/10.1039/d0ob02515a.

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11

Das, Manik, and Kuntal Manna. "Bioactive Cyclohexenones: A Mini Review." Current Bioactive Compounds 11, no. 4 (2015): 239–48. http://dx.doi.org/10.2174/157340721104151230104138.

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12

Holmes, Andrew B., and Nigel C. Madge. "Synthesis of 4,4-disubstituted cyclohexenones." Tetrahedron 45, no. 3 (1989): 789–802. http://dx.doi.org/10.1016/0040-4020(89)80110-3.

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13

Zaidlewicz, M., W. Sokól, A. Wolan, et al. "Enolboration of conjugated ketones and synthesis of beta-amino alcohols and boronated alpha-amino acids." Pure and Applied Chemistry 75, no. 9 (2003): 1349–55. http://dx.doi.org/10.1351/pac200375091349.

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Enolization–aldolization of conjugated ketones, enantioselective synthesis of benzofuryl beta-amino alcohols, and synthesis of p-dihydroxyborylphenylalanine (BPA) and its analogs are described. Aldolization of benzaldehyde with lithium dienolates derived from unhindered conjugated cyclohexenones favored anti- selectivity, whereas syn selectivity was favored for hindered cyclohexenones. Anti-aldols were preferentially formed from dienolborinates derived from conjugated cyklohexenones, however,competing aldolization at the 2-position was observed for hindered ketones. Benzofuryl beta-amino alcoh

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14

Yang, Hongzhou, Qingqing Wang, Yuan Luo, et al. "Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1607–11. http://dx.doi.org/10.1039/d0ob00004c.

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15

Podraza, Kenneth F. "REGIOSPECIFIC ALKYLATION OF CYCLOHEXENONES. A REVIEW." Organic Preparations and Procedures International 23, no. 2 (1991): 217–35. http://dx.doi.org/10.1080/00304949109458319.

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16

Kündig, E., Manisankar Sau, and Alejandro Perez-Luna. "Synthesis of 4,5-trans-Substituted Cyclohexenones." Synlett 2006, no. 13 (2006): 2114–18. http://dx.doi.org/10.1055/s-2006-948187.

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17

MIYAOKA, Hiroaki, Shoichi SAGAWA, Tadamichi INOUE, Hiroto NAGAOKA, and Yasuji YAMADA. "Efficient synthesis of optically active cyclohexenones." CHEMICAL & PHARMACEUTICAL BULLETIN 42, no. 2 (1994): 405–7. http://dx.doi.org/10.1248/cpb.42.405.

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18

PODRAZA, K. F. "ChemInform Abstract: Regiospecific Alkylation of Cyclohexenones." ChemInform 22, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199145353.

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19

Meister, Anne C., Paul F. Sauter, and Stefan Bräse. "A Stereoselective Approach to Functionalized Cyclohexenones." European Journal of Organic Chemistry 2013, no. 31 (2013): 7110–16. http://dx.doi.org/10.1002/ejoc.201300752.

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20

Feigenbaum, Alexandre, Yves Fort, Jean Pierre Pete, and Denise Scholler. "Photochemical cyclization of 2-alkyl-3-aryl-2-cyclohexenones and 2-alkoxy-3-aryl-2-cyclohexenones." Journal of Organic Chemistry 51, no. 23 (1986): 4424–32. http://dx.doi.org/10.1021/jo00373a015.

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21

Liang, Yu-Feng, Song Song, Lingsheng Ai, Xinwei Li, and Ning Jiao. "A highly efficient metal-free approach to meta- and multiple-substituted phenols via a simple oxidation of cyclohexenones." Green Chemistry 18, no. 24 (2016): 6462–67. http://dx.doi.org/10.1039/c6gc02674e.

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The simple and readily available I<sub>2</sub> catalyst, and a cheap and common DMSO oxidant could be employed for the transformation of cyclohexenones to meta- and multiple-substituted phenols with significant tolerance to various functional substituents.

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22

Liu, Cheng-Hang, and Zhi-Xiang Yu. "Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (−)-galanthamine." Organic & Biomolecular Chemistry 14, no. 25 (2016): 5945–50. http://dx.doi.org/10.1039/c6ob00660d.

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A Rh-catalyzed [5 + 1] cycloaddition of allenylcyclopropanes and CO has been developed to synthesize functionalized 2-methylidene-3,4-cyclohexenones. This cycloaddition reaction has been utilized as a key step in the formal synthesis of natural product (−)-galanthamine.

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23

Wen, Zhen-Kang, Xiao-Xue Wu, Wen-Kai Bao, Jing-Jing Xiao та Jian-Bin Chao. "Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications". Organic Letters 22, № 12 (2020): 4898–902. http://dx.doi.org/10.1021/acs.orglett.0c01763.

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24

Zhang, Jingwu, Qiangqiang Jiang, Dejun Yang, Xiaomei Zhao, Yanli Dong, and Renhua Liu. "Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors." Chemical Science 6, no. 8 (2015): 4674–80. http://dx.doi.org/10.1039/c5sc01044f.

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A combination of Pd/C and H<sub>2</sub> is found to dehydrogenate a wide range of substituted cyclohexanones and 2-cyclohexenones to their corresponding phenols with high isolated yields, with H<sub>2</sub> as the only byproduct.

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25

Piovano, Marisa, Juan Garbarino, Lamberto Tomassini, and Marcello Nicoletti. "Cyclohexanones from Mimulus glabratus and M. luteus." Natural Product Communications 4, no. 12 (2009): 1934578X0900401. http://dx.doi.org/10.1177/1934578x0900401204.

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The phytochemical study of Mimulus glabratus A. Gray allowed the isolation of two cyclohexenones: the new compound 6-chlorohalleridone 1 and halleridone 2. Halleridone was also identified in Mimulus luteus L., together with dihydroalleridone 3, the naphtoquinone α-dunnione 4, ursolic acid and β-sitosterol.

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26

Adembri, Giorgio, Mirella Scotton, and Alessandro Sega. "The crystal structure and stereochemistry of 2-acetyl-3,5,6-trihydroxy-5,6-dimethyl-2-cyclohexenones." Canadian Journal of Chemistry 66, no. 2 (1988): 246–48. http://dx.doi.org/10.1139/v88-041.

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The stereochemistry of 3a, one of the 2-acetyl-3,5,6-trihydroxy-5,6-dimethylcyclohexenones, obtained by rearrangement of 2,3-diacetyl-4-hydroxy-4-methylcyclopentenone, 2a, under basic conditions, was determined by an X-ray crystal structure analysis. An ORTEP plot shows the configuration of (5RS,6RS)-2-acetyl-3,5,6-trihydroxy-5,6-dimethylcyclohexenone and the presence of a conjugated chelated system involving the H-bonding between O(3)… H(31) and H(31)… O(2).Crystals of 3a are triclinic, a = 10.979(4), b = 7.766(3), c = 6.382(3) Å, α = 86.23(2), β = 72.86(1), γ = 88.23(2)°, Z = 2, space group

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27

Liu, Xueli, Jun Chen, and Tianlin Ma. "Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones." Organic & Biomolecular Chemistry 16, no. 45 (2018): 8662–76. http://dx.doi.org/10.1039/c8ob02351d.

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Prompted by the scant attention paid by published literature reviews to the comprehensive catalytic dehydrogenative aromatization of cyclohexa(e)nones, this review describes recent methods developed to-date involving transition-metal-catalyzed oxidative aromatization and metal-free strategies for the transformation of cyclohexa(e)nones to substituted phenols.

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28

Roy, Joyeeta, Tanushree Mal, Supriti Jana, and Dipakranjan Mal. "Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins." Beilstein Journal of Organic Chemistry 12 (March 16, 2016): 531–36. http://dx.doi.org/10.3762/bjoc.12.52.

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Dibromobenzoisofuranone 12, synthesized in six steps, was regiospecifically annulated with 5-substituted cyclohexenones 13/36 in the presence of LiOt-Bu to give brominated anthraquinones 14/38 in good yields. Darzens condensation of 30 was shown to give chain-elongated anthraquinone 32. Alkaline hydrolysis of 38 furnished 39 representing desulfoproisocrinin F.

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29

Usami, Hisanao, Katsuhiko Takagi, and Yasuhiko Sawaki. "Regioselective Photocyclodimerization of Cyclohexenones Intercalated on Clay Layers." Chemistry Letters 21, no. 8 (1992): 1405–8. http://dx.doi.org/10.1246/cl.1992.1405.

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30

Hexum, Joseph K., Rodolfo Tello-Aburto, Nicholas B. Struntz, Andrew M. Harned та Daniel A. Harki. "Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling". ACS Medicinal Chemistry Letters 3, № 6 (2012): 459–64. http://dx.doi.org/10.1021/ml300034a.

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31

Chong, Byong-Don, Yong-Il Ji, Seong-Soo Oh, Jae-Deuk Yang, Woonphil Baik, and Sangho Koo. "Highly Efficient Synthesis of Methyl-Substituted Conjugate Cyclohexenones." Journal of Organic Chemistry 62, no. 26 (1997): 9323–25. http://dx.doi.org/10.1021/jo970145x.

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32

Tian, Jie-Feng, Ru-Jian Yu, Xiao-Xia Li, et al. "Cyclohexenones and isocoumarins from an endophytic fungus ofSarcosomataceaesp." Journal of Asian Natural Products Research 17, no. 5 (2015): 550–58. http://dx.doi.org/10.1080/10286020.2015.1043904.

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33

Kraus, George, and Junwon Kim. "A Direct Preparation of 6-Methylene-2-cyclohexenones." Synthesis 2004, no. 11 (2004): 1737–38. http://dx.doi.org/10.1055/s-2004-829162.

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34

Barluenga, J., M. Suero, R. De la Campa, and J. Flórez. "Synthesis of Chiral Cyclohexenones Using a Multicomponent Reaction." Synfacts 2011, no. 02 (2011): 0179. http://dx.doi.org/10.1055/s-0030-1259345.

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35

Houjeiry, Tania I., Sarah L. Poe, and D. Tyler McQuade. "Synthesis of Optically Active 4-Substituted 2-Cyclohexenones." Organic Letters 14, no. 17 (2012): 4394–97. http://dx.doi.org/10.1021/ol301874x.

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36

Meister, Anne C., Paul E. Sauter, and Stefan Braese. "ChemInform Abstract: A Stereoselective Approach to Functionalized Cyclohexenones." ChemInform 45, no. 12 (2014): no. http://dx.doi.org/10.1002/chin.201412055.

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37

MIYAOKA, H., S. SAGAWA, T. INOUE, H. NAGAOKA, and Y. YAMADA. "ChemInform Abstract: Efficient Synthesis of Optically Active Cyclohexenones." ChemInform 25, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199437030.

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38

Jaladhi, A., Vasavada, and H. Parekh H. "Synthesis and antimicrobial screening of cyclohexenones and oxazines." Journal of Indian Chemical Society Vol. 80, Jan 2003 (2003): 55–56. https://doi.org/10.5281/zenodo.5835846.

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Department of Chemistry. Saurashtra University. Rajkot-360 005, India <em>E-mail:</em> hhparekh@yahoo.com Fax : 91-0281-78512 <em>Manuscript received 1 February 2002. accepted 21 August 2002</em> 4-Cinnamoyloxybenzylidene (1) on condensation with various ketones yielded 1-aryl-3-(4'-cinnamoyloxypheny1)-2-propene-1-ones (2), which on cyclization with ethyl acetoacetate in acetone and urea in alcoholic KOH furnished 6-carbethoxy-5-(4'-cinnamoyloxypheny1)- 3-aryl-1-cyclohexenones (3a-h) and 2-imino-4-aryl-6-(4'-cinnamoyloxyphenyl)-6<em>H</em>-2,3-dihydro-1,3-oxazines (4a-h), respectiv

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39

Ren, Hong-Xia, Xiang-Jia Song, Lin Wu, et al. "Substituted (E )-2-Methylene-3,4-cyclohexenones through Direct and Convenient Synthesis from Cyclohexenone-MBH Alcohol in the Presence of DMAP." European Journal of Organic Chemistry 2019, no. 4 (2018): 715–19. http://dx.doi.org/10.1002/ejoc.201801301.

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40

Li, Lu, Na Li, Xiao-Tian Mo, Ming-Wei Yuan, Lin Jiang, and Ming-Long Yuan. "Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines." Beilstein Journal of Organic Chemistry 20 (July 2, 2024): 1468–75. http://dx.doi.org/10.3762/bjoc.20.130.

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A catalyst- and additive-free synthesis of 2-benzyl N-substituted anilines from (E)-2-arylidene-3-cyclohexenones and primary amines has been reported. The reaction proceeds smoothly through a sequential imine condensation–isoaromatization pathway, affording a series of synthetically useful aniline derivatives in acceptable to high yields. Mild reaction conditions, no requirement of metal catalysts, operational simplicity and the potential for scale-up production are some of the highlighted advantages of this transformation.

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41

Ayer, William A., Türkan Gökdemir, Shichang Miao, and Latchezar S. Trifonov. "Leptosphaerones A and B, New Cyclohexenones from Leptosphaeria herpotrichoides." Journal of Natural Products 56, no. 9 (1993): 1647–50. http://dx.doi.org/10.1021/np50099a034.

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42

Peña, Javier, Ana B. Antón, Rosalina F. Moro, Isidro S. Marcos, Narciso M. Garrido, and D. Díez. "Tandem catalysis for the synthesis of 2-alkylidene cyclohexenones." Tetrahedron 67, no. 43 (2011): 8331–37. http://dx.doi.org/10.1016/j.tet.2011.08.068.

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43

Differding, Edmond, Oscar Vandevelde, Bertrand Roekens, Tran Trieu Van, and Léon Ghosez. "A versatile method of synthesis of anilines and cyclohexenones." Tetrahedron Letters 28, no. 4 (1987): 397–400. http://dx.doi.org/10.1016/s0040-4039(00)95738-1.

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44

Lechuga-Eduardo, Harim, Eduardo Zarza-Acuña, and Moisés Romero-Ortega. "Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization." Tetrahedron Letters 58, no. 33 (2017): 3234–37. http://dx.doi.org/10.1016/j.tetlet.2017.07.007.

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45

Carlone, Armando, Mauro Marigo, Chris North, Aitor Landa, and Karl Anker Jørgensen. "A simple asymmetric organocatalytic approach to optically active cyclohexenones." Chem. Commun., no. 47 (2006): 4928–30. http://dx.doi.org/10.1039/b611366d.

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46

PATTERSON, J. W. "ChemInform Abstract: The Alkylation of 3-Chloro-2-cyclohexenones." ChemInform 23, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199241112.

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47

Gharpure, Santosh, P. Niranjana, and Suheel Porwal. "Cascade Radical Cyclization to Vinylogous Carbonates/Carbamates for the Synthesis of Oxa- and Aza-Angular Triquinanes: Diastereoselectivity Depends on the Ring Size of Radical Precursor." Synthesis 50, no. 15 (2018): 2954–67. http://dx.doi.org/10.1055/s-0036-1589541.

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An efficient strategy was developed for the stereoselective construction of oxa- and aza-angular triquinanes employing a cascade 5-exo-trig radical cyclization to vinylogous carbonates and carbamates. The radical precursors are readily prepared from 2-(hydroxymethyl)cyclopentenone/cyclohexenones. High diastereoselectivity is observed for the formation of angular oxa- and azatriquinanes. Diastereoselectivity drops when six-membered radical precursors are used. The strategy is found to be useful to incorporate synthetically challenging moieties such as spiroindoline, lactone-bearing, and uracil-

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48

ASAOKA, Morio, and Hisashi TAKEI. "The chemistry of (R)- and (S)-5-trimethylsilyl-2-cyclohexenones." Journal of Synthetic Organic Chemistry, Japan 48, no. 3 (1990): 216–28. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.216.

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49

Chênevert, Robert, and Daniel Chamberland. "INFLUENCE OF CYCLODEXTRINS ON THE SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES." Chemistry Letters 14, no. 8 (1985): 1117–18. http://dx.doi.org/10.1246/cl.1985.1117.

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50

Chêneverst, Robert, and Guy Ampleman. "SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES IN THE PRESENCE OF AMYLOSE." Chemistry Letters 14, no. 10 (1985): 1489–90. http://dx.doi.org/10.1246/cl.1985.1489.

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