18690-79-4

Upstream product

• 58-27-5 menadione 
• 94-36-0 dibenzoyl peroxide 
• 17015-99-5 2-methyl-3-chloronaphthoquinone 
• 98-80-6 phenylboronic acid 
• 673-32-5 1-Phenylprop-1-yne 
• 423-39-2 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane 
• 107-18-6 allyl alcohol 
• 591-51-5 phenyllithium 
• 483-55-6 phthiocol 
• 2348-77-8 2-phenyl[1,4]naphthoquinone 
• 75-65-0 tert-butyl alcohol 
• 869476-53-9 3-methyl-4H-spiro[naphthalene-1,2′-[1,3]dioxolan]-4-one 
• 100-58-3 phenylmagnesium bromide 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine-Urea Bifunctional Organocatalyst

An organocatalytic enantioselective epoxidation of 2,3-disubstituted naphthoquinones with tert-butyl hydroperoxide as an oxidant was developed using a guanidine-urea bifunctional catalyst lacking C2 symmetry, which was designed based upon the insights obtained from the DFT calculation model for our previous C2 symmetric catalyst. The present organocatalytic reaction provides access to a variety of optically active naphthoquinone epoxides bearing aryl and methyl substituents at C2 and C3 in high yields with high enantioselectivities (up to 97:3 er).

New, simple and selective synthesis of perfluoroalkylquinones by perfluoroalkyl radicals - Enthalpic and polar effects

Perfluoroalkyl radicals (Rf), generated by iodine abstraction from perfluoroalkyl iodides by phenyl radicals, react selectively with quinone rings in spite of their electrophilic character. In the presence of electron-rich alkenes, Rf/sub

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

Iron-Catalyzed Radical Methylation of Activated Alkenes with tert -Butanol as the Methyl Source

A free-radical-initiated methylation/addition/cyclization of N -arylacrylamides and a methylation/addition/elimination of quinines have been developed in which t -BuOH is used as a methyl source. These reactions provide effective and selective methods for the synthesis of various methylated oxindoles and quinones in moderate to good yields.

NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.

Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent

Oxidative stress due to the overproduction of reactive oxygen species plays an important role in the pathogenesis of various diseases. In the present study, we comprehensively evaluated the antioxidant activities of 147 oral formulations of Japanese traditional herbal medicines (Kampo medicines), representing the entire panel of oral Kampo medicines listed in the Japanese National Health Insurance Drug List, using in vitro radical scavenging assays, including the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity assay, the superoxide anion scavenging activity assay, and the oxygen radical absorption capacity assay. Three of the formulations tested, namely, Tsudosan, Daisaikoto, and Masiningan, showed the most potent in vitro antioxidant activities and were selected for further investigation of their intracellular and in vivo antioxidant effects. The results of the 2′,7′-dichlorodihydrofluorescin diacetate assay demonstrated that all three Kampo medicines significantly inhibited hydrogen peroxide-induced oxidative stress in human hepatocellular liver carcinoma HepG2 cells. In addition, Tsudosan significantly increased the serum biological antioxidant potential values when orally administrated to mice, indicating that it also had in vivo antioxidant activity. The potent antioxidant activity of Tsudosan may be one of the mechanisms closely correlated to its clinical usage against blood stasis.

Synthetic method for 2-substituted-1,4-naphthoquinone derivatives

The invention discloses a synthetic method for 2-substituted-1,4-naphthoquinone derivatives. The method comprises the following steps: with 2-alkynylacetophenone compounds as shown in a formula I which is described in the specification as a raw material and dimethyl sulfoxide as an oxidizing agent and a solvent, carrying out a reaction at 80 to 140 DEG C under stirring and the action of a copper catalyst for 2 to 10 h; and subjecting a reaction solution obtained after completion of the reaction to post-treatment so as to obtain the 2-substituted-1,4-naphthoquinone derivatives as shown in a formula II which is described in the specification, wherein the copper catalyst is a mixture of bis(copper trifluoromethanesulfonate) and an inorganic cuprous salt, and the inorganic cuprous salt is one selected from a group consisting of cuprous iodide, cuprous chloride, cuprous bromide and cuprous cyanide. The method has the advantages that the raw materials are variable; the number of the prepared derivatives is great; the catalyst is cheap and easily available; cost is substantially reduced; no pollution is produced; no extra oxidizing agent is needed; dimethyl sulfoxide both functions as the oxygen source and the solvent, so cost is saved; and the method has the characteristics of high reaction yield, good substrate applicability, simple operation, etc.

Method for synthesizing 2-substituted-1,4-naphthoquinone compound

The invention discloses a method for synthesizing a 2-substituted-1,4-naphthoquinone compound. The method comprises the following steps: by taking a 2-alkynyl acetophenone compound of a formula I as shown in the specification as a raw material, in the presence of a copper catalyst, by taking Selectfluor as an oxidant, adding an alkali substance, performing a stirring reaction for 10-24 hours at 70 DEG C in a mixed solvent of acetonitrile and water, and after the reaction is completed, and performing aftertreatment on reaction liquid, thereby obtaining the 2-substituted-1,4-naphthoquinone compound of a formula II as shown in the specification. By adopting the method disclosed by the invention, the raw materials are variable, a great amount of derivatives can be generated, the catalyst is cheap and easy to obtain, the cost can be greatly lowered, and no pollution can be caused; oxygen sources used in the method are water and Selectfluor; the reaction condition is gentle, and energy consumption can be reduced; in addition, the method has the characteristics of being high in yield, good in substrate universality, simple and convenient in aftertreatment operation, and the like.

Tuning the redox potential of Vitamin K3 derivatives by oxidative functionalization using a Ag(i)/GO catalyst

We propose herein initial results to develop optimum redox mediators by the combination of computational simulation and catalytic functionalization of the core structure of vitamin K3. We aim to correlate the calculated energy value of the LUMO

Microwave-assisted solid-phase D?tz benzannulation reaction: A facile synthesis of 2,3-disubstituted-1,4-naphthoquinones

A microwave-assisted solid-supported D?tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1, 4-naphthoquinone derivatives in good to moderate yields with high purities.