32745-55-4

Usage

Type

Chemical compound

Derivative of

Anthracene

Physical state

Yellow crystalline solid

Melting point

Around 346 degrees Celsius

Stability

Stable under normal conditions

Reactivity

Can react violently with strong oxidizing agents

Applications

a. Organic synthesis
b. Building block in organic electronic materials
c. Dye
d. Intermediate in pharmaceuticals and agrochemicals production
e. Potential use in organic electronic devices (e.g., organic field-effect transistors and organic light-emitting diodes)

InChI:InChI=1/C15H10O2/c16-14-10-3-1-2-4-11(10)15(17)13-9-6-5-8(7-9)12(13)14/h1-6,8-9H,7H2

Upstream product

• 52457-24-6 1,4-dihydro-1,4-methanoanthracene-9,10-diol 
• 33741-23-0 endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone 
• 127709-12-0 exo tetracyclo<10.2.1.0^2,11.0^4,9>pentadeca-4,5,7,13-tetraene-3,10-dione 
• 24402-95-7 1,4,4a,9a-Tetrahydro-1,4-endomethylen-anthrachinon 
• 106-94-5 propyl bromide 
• 542-92-7 cyclopenta-1,3-diene 
• 134281-84-8 (+)-(SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone 
• 24402-95-7 1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 75171-64-1 C₁₅H₁₂O₃ 
• 75171-66-3 C₁₅H₁₂O₃ 

Relevant academic research and scientific papers

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.

Oxidative dehydrogenation and the aromatization of polycycles using o-iodoxybenzoic acid (IBX)

An efficient and convenient method for the dehydrogenation and aromatization of various polycycles using o-iodoxybenzoic acid (IBX) is described.

Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes

Acid promoted ring opening of 1α,4α,4aα,9aα-tetrahydro-2β-3β- epoxy-l,4-methanoanthracene-9,10-dione and the corresponding 2-methyl derivative (i.e., 3a and 3b, respectively) afforded 4a and 4b in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 4b along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of 1α,4α-dihydro-4aα,9aα-epoxy- 1,4-methanoanthracene-9,10-dione (12) resulted in extensive skeltal rearrangement of the substrate, thereby affording 14 in low yield.

Formation of tetracyclo[10.2.n.02,11.04,9]pentadeca-2,4,5,7,13-pentaene-3,10 -diones and related systems induced by samarium diiodide

The reaction of either endo or exo tetracyclo[10.2.n.02,11.04,9]penta deca-4,5,7,13-tetraene-3,10-diones with SmI2 led to efficient formation of oxidized title quinones.

Asymmetric Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-naphthoquinones

The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored.The high ? facial diastereoselectivity observed can be reversed in the presence of ZnBr2.Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group.The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

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.