Relevant bibliographies by topics / Carvone selectivity

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Academic literature on the topic 'Carvone selectivity'

Author: Grafiati
Published: 4 June 2025
Last updated: 23 June 2025

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Journal articles on the topic "Carvone selectivity"

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Nikitin, K., T. Osadchaya, A. Afineevskiy, А. Meledin, N. Salnikova, and E. Smirnov. "SELECTIVE LIQUID PHASE REDUCTION OF CARVONE TO CARVEOL ON Pd/Al2O3." Transaction Kola Science Centre 15, no. 1 (2024): 314–18. https://doi.org/10.37614/2949-1215.2024.15.1.052.

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Carveol is used in many different industries, some as an ingredient in flavors or pharmaceuticals. A method for obtaining carveol through the hydrogenation of carvones is considered. Various catalyst loading values, temperatures, and the nature of the solvent are considered. The optimal conditions for the hydrogenation of carvones under mild conditions, in various solvents and at various temperatures were determined. Conditions have been found under which complete conversion of carvones is achieved, and the maximum selectivity of the catalysts for carveol is also achieved. It has been established that selective hydrogenation of the carbonyl group of carvone is an alternative route, however, research is limited by the low yield of the target compound, so it is relevant to study the route of selective reduction of carvone to carveol.
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2

Vrbková, Eva, Adéla Šímová, Eliška Vyskočilová, Miloslav Lhotka, and Libor Červený. "Acid Treated Montmorillonite—Eco-Friendly Clay as Catalyst in Carvone Isomerization to Carvacrol." Reactions 2, no. 4 (2021): 486–98. http://dx.doi.org/10.3390/reactions2040031.

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Acid-treated montmorillonites (MMT) were used as catalysts of carvone isomerization to carvacrol. Mineral acids—sulfuric, hydrochloric, nitric acids and organic acids (acetic and chloroacetic)—were used for the acid treatment. Prepared materials were characterized by available characterization methods, namely XRD, EA, TPD, TPO, UV-Vis, laser light scattering and nitrogen physisorption. The structure of montmorillonite remained intact after treatment. However, TPD proved the increase of acidity of acid-treated materials comparing pure montmorillonite. All materials were tested in the isomerization of carvone, producing carvacrol as the desired product. The initial reaction rate increased using the materials in the row MMT-COOH < MMT-HNO3 < MMT-ClCOOH < MMT-H2SO4 < MMT-HCl, which is in accordance with the pKa of acids used for the treatment. The number of weak acid sites strongly influenced the selectivity to carvacrol. The optimal solvent for the reaction was toluene. Total conversion of carvone and the selectivity to carvacrol 95.5% was achieved within 24 h under 80 °C, with toluene as solvent and montmorillonite treated by chloroacetic acid as catalyst. The catalyst may be reused after calcination with only a low loss of activity.
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3

Dr., Tuğba Gürmen Özçelik. "Selective Oxidation of Limonene over γ-Al2O3 Supported Metal Catalyst with H2O2". International Journal of Engineering and Management Research 8, № 4 (2018): 208–12. https://doi.org/10.31033/ijemr.v8i4.13243.

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Liquid phase oxidation of limonene by hydrogen peroxide over the CeO2 and Fe2O3 catalysts supported by γ- Al2O3 was reported. Etly acetate and acetone were used as solvent to investigate the effect of the solvent on the oxidation reaction. The experiments were carried out at 80 °C The conversion of limonene and the selectivities of the carvone were calculated during the 10h reaction time. According to experimental results, maximum conversion of limonene and product selectivity of carvone were obtained with CeO2-γAl2O3 catalyst as 85% and 41%, respectively end of the 10 h reaction. The XRD analysis of the CeO2- γAl2O3 catalyst were performed.
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4

Morrison, Christopher F., Jamie P. Vaters, David O. Miller, and D. Jean Burnell. "Facial selectivity in the 4 + 2 reactions of a diene derived from carvone." Organic & Biomolecular Chemistry 4, no. 6 (2006): 1160. http://dx.doi.org/10.1039/b516675f.

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5

Kelly, Lawrence F., and Geoffrey J. Deeble. "Selectivity in organic synthesis: chemo- and regiospecific reductions of carvone: An undergraduate experiment." Journal of Chemical Education 63, no. 12 (1986): 1107. http://dx.doi.org/10.1021/ed063p1107.

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6

Li, Yizhou, Yepeng Yang, Daomei Chen, et al. "Liquid-Phase Catalytic Oxidation of Limonene to Carvone over ZIF-67(Co)." Catalysts 9, no. 4 (2019): 374. http://dx.doi.org/10.3390/catal9040374.

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Liquid-phase catalytic oxidation of limonene was carried out under mild conditions, and carvone was produced in the presence of ZIF-67(Co), cobalt based zeolitic imidazolate framework, as catalyst, using t-butyl hydroperoxide (t-BHP) as oxidant and benzene as solvent. As a heterogeneous catalyst, the zeolitic imidazolate framework ZIF-67(Co) exhibited reasonable substrate–product selectivity (55.4%) and conversion (29.8%). Finally, the X-ray diffraction patterns of the catalyst before and after proved that ZIF-67(Co) acted as a heterogeneous catalyst, and can be reused without losing its activity to a great extent.
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7

Elizabeth, Niño-Arrieta, Luz Villa-Holguín Aída, Alexis Alarcón-Durango Edwin, Talavera-López Alfonso, Antonio Gómez-Torres Sergio, and Ariel Fuentes-Zurita Gustavo. "Limonene epoxidation in aqueous phase over Ti/KIT-6." Revista Facultad de Ingeniería -redin-, no. 88 (September 4, 2018): 74–79. https://doi.org/10.17533/udea.redin.n88a08.

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Limonene epoxidation was carried out in the liquid phase using Ti/KIT-6 as the catalyst and tert-butyl hydroperoxide as oxidant. The best selectivity (60%) was obtained at 50 °C after 7 h of reaction, and the conversion was 23%. The main side products were carvone, carveol, 1,2-epoxylimonene diol, perillyl alcohol and p-mentha-2,8-dien-1-ol. The catalyst does not leach under reaction conditions and it can be reused after calcination at 550 ºC. The catalyst was characterized by atomic absorption, XRD, UV-vis and N2 adsorption isotherms.
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8

Mekkaoui, Ayoub Abdelkader, Mouhsine Laayati, Hamza Orfi, Larbi El Firdoussi, and Soufiane El Houssame. "Catalytic Allylic Chlorination of Natural Terpenic Olefins Using Supported and Nonsupported Lewis Acid Catalysts." Journal of Chemistry 2020 (October 22, 2020): 1–8. http://dx.doi.org/10.1155/2020/2563634.

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A mild and convenient method for the allylic chlorination of naturally occurring terpenic olefins was investigated in the presence of different supported and non-supported Lewis acid catalysts. The reaction has been tested on carvone as a model substrate in the presence of sodium hypochlorite as chlorine donor. The scope and limitations of transition metal-based Lewis acid catalysts, stoichiometry, and substrate structure were evaluated. Among the iron precursors used, FeCl3 and FeCl2 provide the promise of a general approach to allylic or vinylic chlorination reaction. Various terpenic olefins were examined in the presence of FeCl3/NaOCl combination system. The catalytic chlorination proceeds under mild conditions with short reaction time and shows a high selectivity affording the corresponding chlorides in good to excellent yields.
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9

Mak, Kendrew K. W., Y. M. Lai, and Yuk-Hong Siu. "Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions." Journal of Chemical Education 83, no. 7 (2006): 1058. http://dx.doi.org/10.1021/ed083p1058.

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10

Moller, Alejandra Catalina, Carol Parra, Bastian Said, et al. "Antioxidant and Anti-Proliferative Activity of Essential Oil and Main Components from Leaves of Aloysia polystachya Harvested in Central Chile." Molecules 26, no. 1 (2020): 131. http://dx.doi.org/10.3390/molecules26010131.

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The aim of this study was to determine, first, the chemical composition of Aloysia polystachya (Griseb) Moldenke essential oil, from leaves harvested in central Chile; and second, its antioxidant and cytotoxic activity. Eight compounds were identified via gas chromatography–mass spectrometry (GC–MS) analyses, with the most representative being R-carvone (91.03%), R-limonene (4.10%), and dihydrocarvone (1.07%). For Aloysia polystachya essential oil, antioxidant assays (2,2-diphenyl-1-picrylhydrazyl (DPPH), H2O2, ferric reducing antioxidant power (FRAP), and total reactive antioxidant potential (TRAP)) showed good antioxidant activity compared to commercial antioxidant controls; and anti-proliferative assays against three human cancer cell lines (colon, HT-29; prostate, PC-3; and breast, MCF-7) determined an IC50 of 5.85, 6.74, and 9.53 µg/mL, and selectivity indices of 4.75, 4.12, and 2.92 for HT-29, PC-3, and MCF-7, respectively. We also report on assays with CCD 841 CoN (colon epithelial). Overall, results from this study may represent, in the near future, developments for natural-based cancer treatments.
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Book chapters on the topic "Carvone selectivity"

1

Taber, Douglass F. "The Overman Synthesis of Briarellin F." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0092.

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Briarellin F 4 is an elegant representative of the complex polycyclic ethers produced by soft corals such as Briareum abestinum. Larry E. Overman of the University of California, Irvine, developed (J. Org. Chem. 2009, 74, 5458) a triply convergent approach to 4, the central feature of which was the Prins-pinacol combination of 1 with 2 to give 3. The aldehyde 2 was assembled by Wittig homologation of the aldehyde 5 with the phosphorane 6, followed by metalation and formylation. The aldehyde 10 was prepared by opening the enantiomerically pure epoxide 8 with the acetylide 9. Hydroboration of carvone 11 could not be effected with sufficient diastereocontrol. As an alternative, the mixture of diols was oxidized to the lactone 12 . Kinetic quench of the derived silyl ketene acetal followed by reduction led to the diastereomerically pure crystalline diol 13. This key intermediate will have many other applications in target-directed synthesis. The ketone 14 was converted to the alkenyl iodide 15 by stannylation of the enol triflate, followed by exposure of the stannane to N-iodosuccinimide. Addition of the alkenyl iodide 15 to the aldehyde 10 gave the diol 1 as an inconsequential 3:1 mixture of diastereomers. This mixture was combined with the aldehyde 2 to give, via Lewis acid–mediated rearrangement of the initially prepared acetal, the aldehyde 3 . The aldehyde 3 was readily decarbonylated by irradiation in dioxane. Face-selective Al-mediated epoxidation of the derived homoallylic alcohol proceeded with 10:1 selectivity, and subsequent MCPBA epoxidation of the cyclohexene was also secured with 10:1 facial control. This set the stage for the triflic anhydride–mediated closure of the six-membered ring ether. The Nozaki-Hiyama-Kishi cyclization of 18 proceeded with remarkable selectivity, delivering briarellin E 19 as a single diastereomer. Dess-Martin oxidation converted 19 into briarellin F 4.
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2

Taber, Douglass F. "The Garg Synthesis of (–)-N-Methylwelwitindolinone C." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0089.

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Of the several welwitindolinones, (–)-N-methylwelwitindolinone C 3 uniquely reverses P-glycoprotein-mediated multiple drug resistance. The preparation of 3 reported (J. Am. Chem. Soc. 2011, 133, 15797) by Neil K. Garg of UCLA illustrates the power in complex target-directed synthesis of late stage C–H functionalization. The starting material 7 for this enantiospecific synthesis was prepared following the Natsume strategy (Chem. Pharm. Bull. 1994, 42, 1393) in the enantiomeric series. Commercial carvone 4 was reduced and protected, then oxidized and equilibrated to the dienone 6. The pivalate efficiently directed the Cu-catalyzed conjugate addition of vinyl magnesium bromide, delivering 7. Hydrolysis of 7 gave 8, to which the bromoindole 9 was added in a conjugate sense to give the adduct as a mixture of diastereomers, of which 1 was the more stable. Exposure of 1 to NaNH2 in t-BuOH presumably generated the benzyne [indolyne] 10, which cyclized to the ketone 2. The silyl ether 2 was deprotected and the alcohol was oxidized to give the diketone, which was selectively carried on to the enol triflate and thus to the stannane 11. The alkenyl chloride of the natural product was installed by the oxidation of 11 with CuCl2. Further oxidation with N-bromosuccinimide then delivered the oxindole 12. In the last stage of the synthesis, it was necessary to selectively aminate one of the bridgehead C–H’s of 12. To this end, the ketone was reduced and carried on to the carbamate 13. Attempts to oxidatively cyclize 13 with Rh catalysts failed, but Ag was successful, delivering 14. The final conversion of 15 to (–)-N-methylwelwitindolinone C 3 was achieved by exposure to the Kim reagent 16.
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