33741-23-0

Basic information

• Product Name: endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone
• Synonyms: endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone
• CAS NO: 33741-23-0
• Molecular Weight: 224.259
• Mol File: 33741-23-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone(33741-23-0)
• EPA Substance Registry System: endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone(33741-23-0)

Safety Data

• Hazardous Substances Data: 33741-23-0(Hazardous Substances Data)

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 32745-55-4 1,4-Methano-1,4-dihydro-9,10-anthraquinone 
• 885-19-8 1,4-dihydro-9,10-anthraquinone 
• 52457-25-7 1,4-dihydro-9,10-dimethoxy-1,4-methanoanthracene 
• 542-92-7 cyclopenta-1,3-diene 
• 130-15-4 [1,4]naphthoquinone 
• 75171-64-1 C₁₅H₁₂O₃ 
• 75171-66-3 C₁₅H₁₂O₃ 
• 71155-61-8 (1RS,10SR,11SR,14RS)-15-oxapentacyclo[8.4.1.1^11,14.0^1,10.0^3,8]hexadeca-3⁽⁸⁾,4,6,12-tetraene-2,9-dione 
• 71127-62-3 C₁₅H₁₀O₃ 
• 32745-55-4 methanoanthraquinone 

Relevant articles and documents

4:2 Diels-Alder adduct of 1,3-cyclopentadiene with 1,4-naphthoquinone

The title compound, 1,4-methano-1,4,4a,9a-tetrahydro- anthracene-9,10-dione, C15H12O2, is a Diels-Alder adduct resulting from a [4+2] cycloaddition of 1,3-cyclopentadiene with p-naphthoquinone.

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.