79054-81-2

Upstream product

• 79054-78-7 trans-2-acetyl-1,4-dimethoxy-3-prop-1-enylnaphthalene 
• 79054-77-6 1-[3-(1-Bromo-propyl)-1,4-dimethoxy-naphthalen-2-yl]-ethanone 
• 79054-76-5 2-acetyl-1,4-dimethoxy-3-propylnaphthalene 
• 79054-75-4 2-acetyl-3-propyl-1,4-naphthoquinone 
• 5813-57-0 2-acetyl-1,4-naphthoquinone 
• 86137-26-0 (+/-)-(1R,3R,4S)-4-hydroxy-5,10-dimethoxy-1,3-dimethylnaphtho<2,3-c>pyran 
• 79054-79-8 trans-2-(1-hydroxyethyl)-1,4-dimethoxy-3-(1-propenyl)naphthalene 
• 86137-26-0 (+/-)-(1R,3R,4R)-4-hydroxy-5,10-dimethoxy-1,3-dimethylnaphtho<2,3-c>pyran 

Relevant academic research and scientific papers

Synthesis of the Aphin-related (+/-)-7.9-Dideoxyquinone A and (+/-)-7,9-Dideoxyquinone A'

The oxidative cyclisation of 3-(1-hydroxyethyl)-,1,4-dimethoxy-2-prop-1-enylnaphthalene with four equivalents of ceric ammonium nitrate to afford two 4-hydroxy-1,3-dimethylnaphthopyran-5,10-quinones with the same stereochemistry as quinones A and A', derivatives of the aphid pigments protoaphin-fb and protoaphin-sl, is described.Certain aspects of the mechanism have been established.

Naphthopyrans by Ring-closure of Substituted Naphthalenes using Potassium t-Butoxide in Dimethylformamide

Two 2-alkenyl-3-hydroxyalkyl-1,4-dimethoxynaphthalenes are cyclised with potassium t-butoxide in dimethylformamide to give 3-alkyl-3,4-dihydro-5,10-dimethoxynaphthopyrans under anaerobic conditions.One of these products is treated with the same solvent and base, but in air, to give the two possible 4-hydroxy derivatives.

Syntheses of Naphthopyran-5,10-quinones using Ceric Ammonium Nitrate

Two 2-(alk-1-enyl)-3-(1-hydroxyalkyl)-1,4-dimethoxynaphthalenes are oxidised with silver(II) oxide to the corresponding naphthoquinones, while oxidation with cerium(IV) ammonium nitrate affords derivatives of the title compounds.