75171-67-4

Usage

Structure

Fused polycyclic aromatic ring system with an epoxy group and a ketone group

Type

Synthetic derivative of anthracene, a tricyclic aromatic hydrocarbon

Applications

Research and laboratory applications

Potential Applications

Pharmaceuticals and materials science

Safety

Handle with caution and follow proper safety protocols due to potential hazards

Functional Groups

Epoxy and ketone groups

Reactivity

Unique structure and reactive functional groups

Hazards

Potential hazards associated with handling and use

Precautions

Proper safety protocols and handling procedures should be followed

Upstream product

• 32740-61-7 1,4-Ethano-1,4-dihydro-9,10-anthraquinone 
• 75102-25-9 C₁₈H₁₈O₄ 
• 132016-30-9 endo-tetracyclo[10.2.2.0^2,11.0^4.9]hexadeca-4,6,8,13-tetraene-3,10-dione 
• 130-15-4 [1,4]naphthoquinone 
• 55431-77-1 (1R,4S)-1,4,4a,9a-Tetrahydro-1,4-ethano-anthraquinone 

Relevant academic research and scientific papers

Studies on quinones. Part 40: Synthesis and cytotoxicity evaluation of anthraquinone epoxides and isomerization products

Aerobic oxidation of 1,4,4a,10a-tetrahydro-1,4-alkano-5,10-anthraquinones and thiophene-analogues in dichloromethane-DBU yielded the corresponding dihydroalkanoquinones which, depending on their structures, react with in situ generated hydroperoxide anion to give quinone epoxides and/or hydroperoxides. The calcium hydroxide-induced rearrangement of quinone epoxides yielded furan-containing angular quinones. The cytotoxic activities of quinone epoxides and their isomerization products were evaluated in vitro against normal human lung fibroblasts (MRC-5) and human cancer gastric epithelial cells (AGS).

Electronic Control of Stereoselectivity. 6. Directionality of Singlet Oxygen Addition to 1,4-Dimethoxynaphthalenes Laterally Fused to Bridged Bicyclic Systems

The photooxygenation in methanol solution of 1,4-dimethoxynaphthalene derivatives having bridged bicyclic systems fused at C2, C3 with rose bengal as sensitizer leads to formation of stereoisomeric epoxynaphthoquinone monoketals.These products, which are readily hydrolyzed in acid solution to the epoxynaphthoquinones, possess an epoxide oxygen which serves as a stereochemical marker for the directionality of singlet oxygen addition.For the norbornyl and norbornenyl cases, endo bonding by 1O2 is preferred; the reverse is true for the pair of bicyclooctenyl derivatives studied.This contrasting stereoselection was compared to the stereochemical consequences of alkaline hydroperoxidation of the corresponding naphthoquinones.In each instance, the reaction course was opposite to that observed with singlet oxygenation.Both processes are analyzed from the theoretical viewpoint, use being made of the photoelectron spectra of the substrate molecules, detailed evaluation of frontier orbital effects, and prevailing ?/? interactions.While the alkaline hydroperoxidation results can be interpreted in terms of standard kinetic and steric control, an understanding of the directionality of 1O2 capture appears dependent on our appreciation of the contributions made by the ? electrons of the bicyclic moieties upon the aromatic ? orbitals.The tilting caused by such interactions is thought to be source of the experimentally observed exo/endo ratios.