3286-01-9

Usage

Uses

Used in Organic Synthesis:
2,7-Dimethylanthraquinone is used as a key intermediate in the synthesis of various organic compounds. Its application is primarily due to its unique molecular structure, which allows for the formation of a wide range of products through different chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,7-Dimethylanthraquinone is used as a building block for the development of new drugs. Its chemical properties make it suitable for the creation of molecules with potential therapeutic applications.
Used in Dye Industry:
2,7-Dimethylanthraquinone is also utilized in the dye industry, where it serves as a starting material for the production of various dyes and pigments. Its yellow color and chemical stability contribute to its use in this application.
Used in Chemical Research:
In the field of chemical research, 2,7-Dimethylanthraquinone is employed as a model compound for studying various chemical reactions and mechanisms. Its unique structure allows researchers to gain insights into the behavior of similar compounds and develop new synthetic strategies.
Overall, 2,7-Dimethylanthraquinone is a versatile compound with a wide range of applications across different industries, including organic synthesis, pharmaceuticals, dyes, and chemical research. Its unique properties and chemical stability make it a valuable asset in the development of new products and the advancement of scientific knowledge.

InChI:InChI=1/C16H14O2/c1-9-3-5-11-13(7-9)16(18)14-8-10(2)4-6-12(14)15(11)17/h3-8,11,13H,1-2H3

Upstream product

• 782-23-0 2,7-dimethylanthracene 
• 42527-76-4 (+/-)-2,7-dimethyl-(4arH.8atH.9acH.10atH)-1,4,4a,5,8,8a,9a,10a-octahydro-anthraquinone 
• 54159-95-4 3,6-dimethyl-anthrone 
• 56218-49-6 1-((1E,3E)-3,7-Dimethyl-octa-1,3,6-trienyl)-piperidine 
• 605-93-6 6-methyl-1,4-naphthoquinone 
• 106-51-4 p-benzoquinone 
• 78-79-5 isoprene 
• 67-66-3 chloroform 
• 10028-15-6 ozone 
• 860531-10-8 4-(3,6-dimethyl-[9]anthryl)-butyric acid 
• 42527-76-4 bis-isoprene-quinone A 
• 42527-76-4 bis-isoprene-quinone A' 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 201230-82-2 carbon monoxide 

Downstream Products

• 782-23-0 2,7-dimethylanthracene 
• 1412499-96-7 2,7-bis[2-(4-cyanophenyl)vinyl]-9,10-dipentyloxy-anthracene 
• 1412937-49-5 C₆₂H₆₂O₂P₂⁽²⁺⁾ 
• 940910-86-1 2,7-bis[2-(4-dimethylamino-phenyl)vinyl]-9,10-dipentyloxy-anthracene 
• 1412499-95-6 2,7-bis-[2-(p-tolyl)-vinyl]-9,10-dipentyloxy-anthracene 
• 86329-22-8 1,8-diamino-2,7-bis-(phenylimino-methyl)-anthraquinone 

Relevant academic research and scientific papers

Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction

The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017

Rigid Core Anthracene and Anthraquinone Linked Nitronyl and Iminoyl Nitroxide Biradicals

The first syntheses of bis(nitronyl nitroxide) and bis(iminoyl nitroxide) (diNN, diIN) biradicals linked through rigid acene core conjugating anthracene (A) and anthraquinone (AQ) units are reported. Computational modeling predicts weak intramolecular exchange in AQ-linked systems, but A-linked biradicals to have ground state multiplicities consistent with the Borden-Davidson disjointness model. Solution electron spin resonance spectra showed inter-radical exchange-coupled triplet states, except for 2,6-AQ biradicals showing isolated spin spectra. Crystallography of the A-linked biradicals shows a key role for inter-radical contacts for molecular packing. DiINs showed lower-dimensional dyad packing with disorder at the radical units: the conformationally more symmetrical diNNs gave staircase one-dimensional or brickwork two-dimensional lattices. Core anthracene unit stacking was only seen in two systems with bromine on the central anthracene ring: the (large) bromine occupies alternate side placement in dyad stacks for the diIN, chain stacks for the diNN. Magnetism of 2,7-A-linked systems showed predominant ferromagnetic intramolecular triplet-singlet splitting of 24-28 K for diNNs and 8 K for diINs, plus weak antiferromagnetic (AFM) interactions from intermolecular contacts. The 2,6-A-linked biradicals showed AFM exchange between spins. Both A and AQ cores offer possibilities for electronic material development, with a combination of multiple radical spins and π-electron-rich acene cores.

Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

An efficient one-pot synthesis of anthraquinones and tetracenediones was achieved vial-proline catalyzed [4+2] cycloaddition of in situ generated azadiene from α,β-unsaturated aldehydes and 1,4-naphthoquinones or 1,4-anthracenedione in good to excellent yield. This protocol constitutes an unprecedented tandem benzannulation that allows one-pot construction of diverse anthraquinones and tetracenediones in the presence of organocatalysts. This methodology was applied successfully to the synthesis of naturally occurring molecules and photochemically interesting phenanthrenequinone derivatives.

Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives

G-quadruplex structures of DNA represent a potentially useful target for anticancer drugs. Stabilisation of this arrangement at the ends of chromosomes may inhibit the action of telomerase, an enzyme involved in immortalization of cancer cells. Appropriately substituted amido anthracenediones are effective G-quadruplex stabilizers, but no information is available as yet on the possible modulation of G-quadruplex recognition and telomerase inhibition produced by the direction of the amide bond. To understand the basis of amido anthracenedione selectivity, we have synthesized a number of derivatives bearing the -CO-NH- or -NH-CO- group linked to the planar anthraquinone (AQ) moiety at 2,6 and 2,7 positions. The various isomers were tested in terms of telomerase inhibition, determined by the TRAP assay, G-quadruplex stabilisation measured by the increase in melting temperature of the appropriately folded oligonucleotide using FRET, and conformational and G4 binding properties examined by molecular modelling techniques. In all cases, enzymatic inhibition and G-quadruplex stabilization were directly related, which strongly supports the proposed molecular mechanism of telomerase interference. Interestingly, the AQ-NH-CO- arrangement performs invariantly better than the AQ-CO-NH- arrangement, showing a clear preference among isomeric derivatives. Theoretical calculations suggest that the former amide arrangement is co-planar with the aromatic system, whereas the latter is tilted by about 30° when considering the most stable conformation. A more extended planar surface would allow more efficient stacking interactions with the quadruplex structure, hence more effective telomerase inhibition.

Remote aromatic stabilization in radical reactions

The rates of free radical reduction of a series of anthracene derivatives and 1-phenyl-4-bromodecane with tributyltin hydride are mediated by the remote aromatic substituent in an apparent through-space interaction. Density functional calculations suggest that this enhancement is not due to direct stabilization of the free radical intermediate, and is likely to be achieved through the interaction of the aromatic moiety with the polarized transition state leading to the intermediate.

Unsymmetrically substituted 2,7-dimethyl-1,8-diarylanthracenes

A synthesis has been developed for 2,7-dimethyl-1,8-di-o-tolylanthracene 4. The cis 4a and trans 4b isomers of this hydrocarbon can be separated and are stable to interconversion at temperatures below 200 °C. The two enantiomers of the trans isomer 4b have chiral cavities and are expected to be useful precursors for chiral reagents or chiral catalysts.

N.M.R. Study of Bond Orders in o- and p-Quinones

The 4J(Me-CC-H) coupling constsnt, previously established as a probe of bond order,1-3 was used to examine bond orders in a number of quinones.It was found that the presence of a quinone moiety does not cause bond localization in aromatic rings adjacent to the quinone ring.

Cycloaddition Reactions of Citral Dienamines with 1,4-Quinones

Cycloaddition reactions of citral dienamines (Ia and Ib) with different 1,4-quinones have been investigated and the products formed are characterized.The unusual elimination of isopentenyl side chain during the Diels-Alder reaction of dienamine (Ia or Ib) with quinones, has been found to be consistent.Aromatisation seems to be the driving force for the elimination which involves cleavage of C - C bond under relatively mild condition.Results obtained in the attempted total synthesis of Va, a regioisomer of compound (V), one of the products obtained in the reaction of Ia with p-benzoquinone, are also presented.

Cycloarenes, a New Class of Aromatic Compounds, IV. - Attempts to Synthesize Cyclononakisbenzene and Cyclodecakisbenzene

With the aim to synthesize 3 the dithiaphane 5 was prepared from which via 6 the anthracenobenzophenanthrenophane 10 was obtained.The corresponding phane-diene 11 was prepared from 5 via 12 and 13.The conformations of 5, 10, and 11 are discussed on the basis of 1H NMR spectra. - Nonoxidative photocyclisation of 11 yielded 14 which was dehydrogenated to yield the new aromatic system 15.The second internal ring closure to 3 so far did not succeed. - As precursors for the synthesis of 4 the dibenzoanthracenophenanthrenophanes 19 and 20 as well as the corresponding phane-dienes 23 and 24 were prepared via 18.Attempts to cyclodehydrogenate to 4 failed.In this context the conformations of 19, 20, 23, and 24 are discussed based on 1H NMR spectra.