1785-65-5

Usage

Uses

Used in Pesticide Synthesis:
Acetic acid 1,4-dioxo-1,4-dihydronaphthalene-2-yl ester is used as an intermediate in the synthesis of Acequinocyl-d25 (A130602), a compound that acts as an inhibitor of mitochondrial electron transport in complex III. This makes it a valuable component in the development of pesticides to control phytophagous mites.
Used in Pesticide Detection:
Due to its role in the synthesis of Acequinocyl-d25, Acetic acid 1,4-dioxo-1,4-dihydronaphthalene-2-yl ester is also utilized in the detection and analysis of pesticides. This application helps in monitoring and ensuring the quality and safety of pesticide products in the agricultural industry.

InChI:InChI=1/C12H8O4/c1-7(13)16-11-6-10(14)8-4-2-3-5-9(8)12(11)15/h2-6H,1H3

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 108-24-7 acetic anhydride 
• 91-20-3 naphthalene 
• 90-15-3 α-naphthol 
• 75-36-5 acetyl chloride 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 524-42-5 1,2-naphthoquinone 
• 13302-67-5 naphthalene-1,2,4-triol 
• 58851-76-6 4-acetyloxy-5,8-dihydronaphthalen-1-yl acetate 

Downstream Products

• 111273-82-6 2-acetoxy-3-p-tolylsulfanyl-[1,4]naphthoquinone 
• 129700-44-3 3-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate 
• 1080645-02-8 2-[4-(p-chlorophenyl)cyclohexyl]-3-acetoxy-1,4-naphthoquinone 
• 6091-04-9 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate 
• 84-79-7 Lapachol 
• 483-55-6 phthiocol 
• 76309-65-4 Acetic acid 3-cyclohexylmethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl ester 
• 1015-97-0 (1,4)-Naphthoquinono<3,2-c>-1H-pyrazole 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 57620-99-2 2-acetyllapachol 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and correlation of cytotoxicity versus redox potential of 1,4-naphthoquinone derivatives

A series of 1,4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoqui

Site-selectivity control in hetero-Diels-Alder reactions of methylidene derivatives of lawsone through modification of the reactive carbonyl group: An experimental and theoretical study

A new perspective on the reactivity of hydroxyquinones was revealed as an acetal derivative of lawsone was synthesized, isolated, and used in tandem Knoevenagel/hetero-Diels-Alder reactions catalyzed by S-proline. The intermediate alkylidene-1,3-diones that were formed in situ reacted with electron rich alkenes to predominantly afford pyrano-1,2-naphthoquinone (β-lapachone) derivatives along with the isomeric pyrano-1,4-naphthoquinone (α-lapachone) derivatives in high to excellent total yields. Interestingly, the highly reactive arylidene-1,3-dione derivatives were found to be stable and isolable. DFT calculations suggest that these hetero-Diels-Alder reactions have a high polar character, taking place through a two-stage one-step mechanism. An analysis of the conceptual DFT indices allows explaining the remarkable site-selectivity observed.

Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides

To explore further the practical uses of highly active manganese (Mn?), a variety of alcohols were treated with Mn?, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.

Process for the preparation of trans-2,3-disubstituted naphthoquinones

The invention concerns a new process for the preparation of naphthoquinones, in particular an improved process for the preparation of 2,3-disubstituted 1,4-naphthoquinones, in the trans configuration.

PROCESS FOR THE PREPARATION OFTRANS-2,3-DISUBSTITUTED NAPHTHOQUINONES

The invention concerns a new process for the preparation of naphthoquinones, in particular an improved process for the preparation of 2,3-disubstituted 1,4- naphthoquinones, in the trans configuration.

Molecular anchors - Mimicking metabolic processes in thiol analysis

The interaction between various novel naphthoquinones and glutathione was explored using a variety of electrochemical techniques. An adamantane derivatised quinone was found to adsorb strongly to carbon surfaces providing a robust film possessing a distin

Oxidation of 1-Naphthols by Lead Tetraacetate in Acetic Acid

A detailed study of the lead tetraacetate-acetic acid oxidation of 1-naphthol, 4-acetoxy-1-naphthol, 2-methyl-1-naphthol, 2,3-dimethyl-1-naphthol and 1,2,3,4-tetrahydro-9-anthrol (17) has been carried out.In the case of 1-naphthol the major product was 4-acetoxy-1-naphthol (4), with 2,2-diacetoxynaphthalen-1(2H)-one (2) being the only other product formed in significant yield.Attack at C4 was again the main reaction with 4-acetoxy-1-naphthol, which gave 1,4-naphthoquinone as the major product.Acetoxylation occurred predominantly at C2 with 2-methyl-1-naphthol and 2,3-dimethyl-1-naphthol to give the naphthalen-1(2H)-ones (11) and (12) respectively.In both cases minor amounts of 4-acetoxylated derivatives and quinones were also produced. 1,2,3,4-Tetrahydro-9-anthrol (17) gave an analogous set of products, the yields of which showed as unusual concentration dependence.In dilute solution 10-acetoxy-1,2,3,4-tetrahydro-9-anthrol (19) was produced in high yield, whereas with a high substrate concentration a good yield of 9a-acetoxy-1,2,3,4-tetrahydroanthracen-9(9aH)-one (18) was obtained.

OXYGENATION OF AROMATIC AND ALIPHATIC HYDROCARBONS BY A NEW REAGENT SYSTEM, Fe(CH3CN)6(2+)-H2O2-Ac2O: AN EFFECTIVE MODEL REAGENT FOR MONO-OXYGENASE

Reactions of aromatic and aliphatic hydrocarbons with a new system, Fe(CH3CN)6(2+) - H2O2 - Ac2O in CH3CN, gave oxygenation products with fairly high reaction efficiency ( Tables I and II )compared to known to reagent systems used as enzyme models for mono-oxygenases.Investigations of the mechanism of these reactions indicated the involvement of either complex C.FeIV(OH)(OAc)(2+), or complex D, FeIV(OAc)(2+), dependig on the organic substrate.Keywords-oxygenation; aromatic hydrocarbon; aliphatic hydrocarbon; hexakisacetonitrile iron(II) perchlorate; hydrogen peroxide; enzyme model; mono-oxygenase