16294-32-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 809, 1981 DOI: 10.1021/jo00317a034

Upstream product

• 512-56-1 trimethyl phosphite 
• 79015-49-9 anthracene-1,5-diamine 
• 6448-90-4 1,5-dimethoxy-anthraquinone 
• 75829-87-7 1,5-dimethoxy-9,10-dihydro-9,10-anthracenediol 
• 75829-91-3 1,5-dimethoxy-9,10-dihydro-anthracene 
• 67-56-1 methanol 
• 607-62-5 anthracene-1,5-diol 
• 82-46-2 1,5-Dichloroanthraquinone 
• 117-12-4 1,5-dihydroxyanthraquinone 
• 121564-40-7 1,5-bis(methoxymethoxy)-9,10-anthraquinone 

Downstream Products

• 100466-92-0 9,10-Dihydro-3,13-dimethoxy-9,10-<1',2'>benzenoanthracen-1,4-diol 

Relevant academic research and scientific papers

COMPOUNDS AND METHODS OF TREATING RNA-MEDIATED DISEASES

The present invention provides compounds, compositions thereof, and methods of using the same.

A New Convenient Synthesis of Alkoxyanthracenes from Alkoxy-9,10- anthraquinones

Methoxy-9,10-anthraquinones with mono-, di- and tetraether groups at different positions 1a-h can be directly reduced to the corresponding methoxyanthracenes 3a-h in moderate to good yields by zinc in refluxing acetic acid. Under similar conditions, ethyl 1′-anthracenoxyacetate (3i) with the ester group unaffected and 1,8-oxybis(ethyleneoxyethyleneoxy)anthracene (5) were also conveniently synthesized in 65 and 70% yields, respectively.

A BIFUNCTIONAL ANTHRAQUINONE SYNTHON

Commercially available antrarufin has been converted into a bifunctional reagent which will be useful for the preparation of anthraquinone C-glycosides.

ESR Spectroscopic Detection of Intramolecular Interactions in Radical Cations of Poly(α-methoxy)triptycenes

-Cycloaddition of 1,4-benzoquinone to the di- and tetra(α-methoxy)anthracenes 11 yields the diketones 12 which undergo an acid-catalyzed rearrangement to the triptycene hydroquinones 13.Methylation of 13 affords the poly(α-methoxy)triptycenes 4.Aluminium chloride in nitromethane oxidizes the triptycenes 4 to the radical cations 4+* having one 1,4-dialkoxybenzene ring (4b+*, 4c+*, 4e+*) or two (4a+*) or three (4d+*), respectively, of such potential radical centers.The protons of the radical center give rise to hyperfine splittings which are very similar to those found in the ESR spectra of simple cis-1,4-dialkoxybenzene radical cations.The other aromatic protons, but not the bridgehead protons, exhibit a long range hyperfine coupling of 0.011 mT.Selective line broadening in the ESR spectrum of the radical cation 4a+* indicates that intramolecular electron transfer between the 1,4-dimethoxybenzene moieties occurs at a moderate rate.The deceleration of the exchange rate compared to the rate expected for a free radical cation is interpreted in terms of ion pairing.