82864-14-0

Upstream product

• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 91-57-6 2-Methylnaphthalene 
• 7469-77-4 2-methylnaphthalen-1-ol 
• 58-27-5 menadione 

Downstream Products

• 483-55-6 phthiocol 
• 59147-84-1 2-(2-hydroxyethyl)thio-3-methyl-1,4-naphthoquinone 
• 70691-68-8 3-methyl-2-(phenylthio)-1,4-naphthoquinone 
• 58-27-5 menadione 
• 91345-20-9 (2-lactoyl-phenyl)-glyoxylic acid 
• 53948-68-8 2-Hydroxy-2-methyl-2,3-dihydro-[1,4]naphthoquinone 
• 55464-54-5 2,3,4-Trihydro-5-methyl-benzochinoxalin-6-on 
• 1246635-51-7 2-methyl-3-(4-bromophenylthio)-1,4-naphthalenedione 

Relevant academic research and scientific papers

Mesostructured vanadia-alumina catalysts for the synthesis of vitamin K3

Liquid-phase selective oxidation of 2-methylnaphtalene to the vitamin K3 was investigated on a series of mesostructured vanadia-alumina catalysts with different V/Al ratios (0.1-1). They were prepared by the co-precipitation of ammonium metavanadate and aluminum nitrate at pH 5 and characterized by XRD, Raman, TG-DTA, elemental analysis and adsorption-desorption isotherms of nitrogen at -196 °C. The influence of the catalyst composition and calcination temperature upon the physico-chemical properties were closely investigated in relation with the catalytic performances. The result of this investigation indicated the catalysts containing a higher vanadium loading and calcined at 300 °C as the most active. Thus, the VAl07 catalyst led to a selectivity in vitamin K3 of 54% for a conversion of 2-methylnaphtalene of 76%. Such an activity corresponded to mixtures where metavanadate (Raman line at 940 cm-1) and decavanadate (Raman line at 990 cm-1) species were the most abundant. No lines of V2O5 (around 705 cm-1) were detected in the catalysts calcined below 600 °C.

Fabrication, characterization and structure activity relationship of Co and Mn encapsulated on magnetic nanocomposite and its application in one-pot tandem synthesis of various tetrazoles and vitamin K3

Considering the importance of vitamin K3 in commercial pet foods, veterinary medicines, poultry, and some swine feed and also tetrazole derivatives in pharmacy, medicine, chemistry, petroleum, and military industry, design efficient catalytic systems are desirable. Herein, four magnetic nanocomposites (MNCs) of cobalt and manganese using metformin, 3-aminopropyltrimethoxysilane (L1) and 2-aminoethyl-3-aminopropyltrimethoxysilane (L2) were designed and constructed as an efficient and controllable catalytic system. The synthesized nanocomposites fully characterized by FT-IR, AAS, ICP-OES, BET, CHN elemental analysis, SEM, TEM, DLS, EDX, TGA, VSM, and XPS spectroscopy. The well-prepared magnetically recoverable nanocomposites were used in the synthesis of a wide derivatives of α-hydrazino tetrazoles (α-HyT), ferrocenyltetrazoles (FcT), arylaminotetrazoles (ArAT) and also vitamin K3. Besides, the effect of operating parameters, such as the amount of catalyst, nature of solvent, temperature and reaction time, metal nature, chain length and hydrophobicity properties of linkers, was studied in the catalytic efficiency of synthesized nanocatalysts. The best catalytic results were obtained in the following order: FS-L2-Met@Co(II) > FS-L2-Met@Mn(II) > FS-L1-Met@Co(II) > FS-L1-Met@Mn(II) due to their structural characteristics. In addition to high TOF, these magnetic nanocomposites are superior in easy, inexpensive, and commercially preparation, keeping the structural and magnetic characteristics, easy magnetically separation from the reaction medium, short reaction time, mild reaction condition, easy work-up, and reusability without any metal leaching in six runs. Graphical abstract: [Figure not available: see fulltext.]

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.

Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies

A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.

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.

Heterogeneous epoxidation of menadione with hydrogen peroxide over the zeolite imidazolate framework ZIF-8

The zeolite imidazolate framework ZIF-8 exhibits superior catalytic performance in the epoxidation of the electron-deficient CC bond in menadione using aqueous hydrogen peroxide as the oxidant. The catalysis has a truly heterogeneous nature and the framework structure remains intact. This is the first example of oxidation catalysis with ZIF-8.

Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values.

Novel phthiocol-based organometallics with tridentate coordination motif and their unexpected cytotoxic behaviour

Novel phthiocol-based organometallics with in situ formed tridentate N,O,O-coordination motif were established via three-component microwave assisted one-pot reaction. These complexes exhibited enhanced stability in aqueous solution compared to the parental compound KP2048 and showed unexpected cytotoxic behaviour and selectivity in 2D and 3D cell cultures.

Method for preparing epoxide by one-pot olefin aerobic epoxidation

The invention relates to a method for preparing an epoxide by one-pot olefin aerobic epoxidation, and belongs to the technical field of organic synthesis. An olefin, an alkyl aromatic compound and analkali are added into a solvent, or an olefin, an alkyl aromatic compound and an alkali are directly mixed; the temperature is raised to 70-160 DEG C in an air or oxygen atmosphere; reacting is carried out for 1-48 hours; and the olefin is directly oxidized into the corresponding epoxide in the presence of the alkyl aromatic compound, the alkali and air (or oxygen), wherein the yield is up to 99%.In the reaction process, the generated alkyl peroxide is generated in situ and consumed in situ, so that the concentration of the alkyl peroxide is kept at a lower level; and generated alkyl peroxy free radicals can also react with the olefin to further generate the peroxide, and efficiency is improved. The method has the advantages of simple operation, mild conditions, low raw material cost andno need of special complex equipment, and has a good industrial application prospect.

Method for synthesizing vitamin K3 epoxy derivatives

The invention discloses a method for synthesizing vitamin K3 epoxy derivatives. The method comprises the following steps: taking a 2-methyl-1,4-naphthoquinone (vitamin K3) derivative (I) as a raw material, taking tetrabutylammonium iodide (TBAI) as a cata