56423-45-1

Upstream product

• 99-49-0 Carvone 
• 6485-40-1 (R)-Carvone 
• 2244-16-8 (-)-Carvone 
• 6485-40-1 (+)-carvone 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 70412-40-7 5-(1-(bromomethyl)-1-hydroxyethyl)-2-methylcyclohex-2-en-1-one 

Downstream Products

• 81679-68-7 8,9-Dihydroxycarvotanaceton-dinitrophenylhydrazon 
• 99-49-0 Carvone 
• 7712-46-1 5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone 
• 7712-37-0 8-hydroxy-p-menthan-2-one 
• 135895-62-4 5-(1-Chloro-2-hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone 
• 135895-61-3 5-(2-chloro-1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 81679-70-1 5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 70412-40-7 5-(1-(bromomethyl)-1-hydroxyethyl)-2-methylcyclohex-2-en-1-one 
• 454-77-3 5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 32226-54-3 trans-sobrerol 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 111323-96-7 C₁₇H₂₄N₂O₃S 
• 83994-34-7 α,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid 

Relevant academic research and scientific papers

Catalytic Performance of Zr-Based Metal–Organic Frameworks Zr-abtc and MIP-200 in Selective Oxidations with H2O2

The catalytic performance of Zr-abtc and MIP-200 metal–organic frameworks consisting of 8-connected Zr6 clusters and tetratopic linkers was investigated in H2O2-based selective oxidations and compared with that of 12-coordinated UiO-66 and UiO-67. Zr-abtc demonstrated advantages in both substrate conversion and product selectivity for epoxidation of electron-deficient C=C bonds in α,β-unsaturated ketones. The significant predominance of 1,2-epoxide in carvone epoxidation, coupled with high sulfone selectivity in thioether oxidation, points to a nucleophilic oxidation mechanism over Zr-abtc. The superior catalytic performance in the epoxidation of unsaturated ketones correlates with a larger amount of weak basic sites in Zr-abtc. Electrophilic activation of H2O2 can also be realized, as evidenced by the high activity of Zr-abtc in epoxidation of the electron-rich C=C bond in caryophyllene. XRD and FTIR studies confirmed the retention of the Zr-abtc structure after the catalysis. The low activity of MIP-200 in H2O2-based oxidations is most likely related to its specific hydrophilicity, which disfavors adsorption of organic substrates and H2O2.

Activation of H2O2over Zr(IV). Insights from Model Studies on Zr-Monosubstituted Lindqvist Tungstates

Zr-monosubstituted Lindqvist-type polyoxometalates (Zr-POMs), (Bu4N)2[W5O18Zr(H2O)3] (1) and (Bu4N)6[{W5O18Zr(μ-OH)}2] (2), have been employed as molecular models to unravel the mechanism of hydrogen peroxide activation over Zr(IV) sites. Compounds 1 and 2 are hydrolytically stable and catalyze the epoxidation of C?C bonds in unfunctionalized alkenes and α,β-unsaturated ketones, as well as sulfoxidation of thioethers. Monomer 1 is more active than dimer 2. Acid additives greatly accelerate the oxygenation reactions and increase oxidant utilization efficiency up to >99%. Product distributions are indicative of a heterolytic oxygen transfer mechanism that involves electrophilic oxidizing species formed upon the interaction of Zr-POM and H2O2. The interaction of 1 and 2 with H2O2 and the resulting peroxo derivatives have been investigated by UV-vis, FTIR, Raman spectroscopy, HR-ESI-MS, and combined HPLC-ICP-atomic emission spectroscopy techniques. The interaction between an 17O-enriched dimer, (Bu4N)6[{W5O18Zr(μ-OCH3)}2] (2′), and H2O2 was also analyzed by 17O NMR spectroscopy. Combining these experimental studies with DFT calculations suggested the existence of dimeric peroxo species [(μ-?2:?2-O2){ZrW5O18}2]6- as well as monomeric Zr-hydroperoxo [W5O18Zr(?2-OOH)]3- and Zr-peroxo [HW5O18Zr(?2-O2)]3- species. Reactivity studies revealed that the dimeric peroxo is inert toward alkenes but is able to transfer oxygen atoms to thioethers, while the monomeric peroxo intermediate is capable of epoxidizing C?C bonds. DFT analysis of the reaction mechanism identifies the monomeric Zr-hydroperoxo intermediate as the real epoxidizing species and the corresponding α-oxygen transfer to the substrate as the rate-determining step. The calculations also showed that protonation of Zr-POM significantly reduces the free-energy barrier of the key oxygen-transfer step because of the greater electrophilicity of the catalyst and that dimeric species hampers the approach of alkene substrates due to steric repulsions reducing its reactivity. The improved performance of the Zr(IV) catalyst relative to Ti(IV) and Nb(V) catalysts is respectively due to a flexible coordination environment and a low tendency to form energy deep-well and low-reactive Zr-peroxo intermediates.

Catalytic β-bromohydroxylation of natural terpenes: Useful intermediates for the synthesis of terpenic epoxides

In a one-step procedure, various β-bromoalcohols were synthesized from natural terpenes in good to excellent yields. Using different catalysts, the reaction was carried out at room temperature, with H2O as nucleophile and N-bromosuccinimide as a bromine source under mild reaction conditions. The synthesized β-bromoalcohols were subsequently converted in situ to the corresponding epoxides in good yields.

Biocidal Compounds from Mentha sp. Essential Oils and Their Structure–Activity Relationships

Essential oils from Greek Mentha species showed different chemical compositions for two populations of M.?pulegium, characterized by piperitone and pulegone. Mentha spicata essential oil was characterized by endocyclic piperitenone epoxide, piperitone epo

Selective catalytic oxidation of alcohols, aldehydes, alkanes and alkenes employing manganese catalysts and hydrogen peroxide

The manganese-containing catalytic system [MnIV,IV 2O3(tmtacn)2]2+ (1)/carboxylic acid (where tmtacn=N,N′,N′′-trimethyl-1,4,7-triazacyclononane), initially identified for the cis-dihydroxylation and epoxidation of alkenes, is applied for a wide range of oxidative transformations, including oxidation of alkanes, alcohols and aldehydes employing H2O2 as oxidant. The substrate classes examined include primary and secondary aliphatic and aromatic alcohols, aldehydes, and alkenes. The emphasis is not primarily on identifying optimum conditions for each individual substrate, but understanding the various factors that affect the reactivity of the Mn-tmtacn catalytic system and to explore which functional groups are oxidised preferentially. This catalytic system, of which the reactivity can be tuned by variation of the carboxylato ligands of the in situ formed [MnIII,III 2(O)(RCO2)2(tmtacn)2]2+ dimers, employs H2O2 in a highly atom efficient manner. In addition, several substrates containing more than one oxidation sensitive group could be oxidised selectively, in certain cases even in the absence of protecting groups. Copyright

Unique salt effect on highly selective synthesis of acid-labile terpene and styrene oxides with a tungsten/Hcatalytic system under acidic aqueous conditions

Acid-labile epoxides such as terpene and styrene oxides are effectively synthesized in high yields with good selectivities using tungsten-catalyzed hydrogen peroxide epoxidation in the presence of NaO The salt effect is thought to originate with the addition of a saturated amount of NaOto aqueous H this addition strongly inhibited the undesired hydrolysis of the acid-labile epoxy products, despite the biphasic conditions of substrate as oil phase and Has acidic aqueous phase.

An effective synthesis of acid-sensitive epoxides via oxidation of terpenes and styrenes using hydrogen peroxide under organic solvent-free conditions

An efficient epoxidation process for various terpenes and styrenes using a hydrogen peroxide-tungsten catalytic system with organic solvent-and halide-free conditions was developed. In the presence of the catalytic system, Na 2WO4, PhP(O)(OH)2, and [Me(n-C 8H17)3N]HSO4, and under weak acidic conditions, hydrogen peroxide successfully epoxidized -pinene to -pinene oxide in 95% selectivity at 91% conversion, while the previously published conditions utilizing NH2CH2P(O)(OH)2 as a promoter provided no epoxide. Georg Thieme Verlag Stuttgart.

Unique salt effect on the high yield synthesis of acid-labile terpene oxides using hydrogen peroxide under acidic aqueous conditions

Acid-labile epoxides such as -pinene oxide are (effectively) synthesized in high yield from the epoxidation of terpenes with aqueous H2O 2 catalyzed by Na2WO4, [Me(n-C 8H17)3N]HSO4, and PhP(O)(OH) 2 in the presence of Na2SO4 as an auxiliary additive under organic solvent-free conditions at ambient temperature. Origin of the salt effect is considered that the addition of a saturated amount of Na2SO4 to aqueous H2O2 strongly inhibited the undesired hydrolysis of the acid-labile epoxide products, despite the highly acidic reaction conditions. Georg Thieme Verlag Stuttgart · New York.

Olefin Epoxidation Using Elemental Fluorine

F2 reacts with water and CH3CN, apparently to produce the relatively stable complex HOF*CH3CN.This is probably the best known oxygen-transfer reagent and can epoxidize olefins quickly and efficiently.Various types of alkenes including aliphatic, benzylic, enones, dienones, maleates, and fumarates have been examined, and all react with the reagent to produce the corresponding mono- or diepoxides in good to excellent yields.This epoxidation is fully stereospecific, and the configuration of the starting olefin is fully retained in the resulting oxirane.In cases where exceptionally stable oxocarbocations can be formed as in 1,1-diphenylethene, the reaction produces vicinal glycols in good yields.Since the origin of the epoxides' oxygen is in the water, this method is very suitable for introducing the isotopes 17O and 18O in various molecules.

HIGHLY EFFICIENT EPOXIDATION OF OLEFINS WITH PYRIDINE N-OXIDES CATALYZED BY RUTHENIUM PORPHYRINS

Oxygen transfer reactions from 2,6-disubstituted pyridine N-oxides to olefins were efficiently catalyzed by ruthenium porphyrins under mild conditions, and various olefins were converted into their epoxides in high yield.