17104-31-3

Upstream product

• 86543-48-8 9-t-butyl-10-methyl-9,10-endotrioxy-9,10-dihydroanthracene 
• 917-64-6 methyl magnesium iodide 
• 1705-82-4 10-diazo-10H-anthracen-9-one 
• 659746-21-1 9,10-bis(1-hydroxymethyl)anthracene-9,10-endoperoxide 
• 7072-00-6 10-methyl-9-anthraldehyde 
• 86543-48-8 9-t-butyl-10-methyl-9,10-endotrioxy-9,10-dihydroanthracene 
• 779-02-2 9-methylanthracene 
• 127-09-3 sodium acetate 
• 98612-72-7 9-Methoxy-10-methyl-anthracen-9,10-ozonid 

Relevant academic research and scientific papers

Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone

A new and never before reported hetero-arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0 (±0.20) × 105 m–1], which is 10 × higher than that described for doxorubicin [Kb = 3.2 (±0.23) × 104 m–1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT-DNA system with a quenching constant (KSV) of 3.3 (±0.3) × 103 m–1 calculated by the Stern–Volmer equation.

REACTION OF 9-t-BUTYL-10-METHYL-9,10-ENDOTRIOXY-9,10-DIHYDROANTHRACENE WITH TRANSITION METAL COMPOUNDS

9-t-butyl-10-methyl-9,10-endotrioxy-9,10-dihydroanthracene underwent reductive decomposition readily with transition metal compounds having one-electron reducibility to result unexpectedly in the specific cleavage of the shorter O-O bond close to the t-butyl group in the trioxide finally giving rise to 10-methyloxanthrone and t-butyl alcohol.A plausible mechanism is discussed.

Endoperoxidation of 9,10-bis(1-hydroxyalkyl)-anthracenes and successive formation of 9,10-anthraquinone under Grignard reaction conditions

The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthr

Competition between nucleophilic addition and electron-transfer process in the reaction of 9-diazo-10-anthrone with Grignard reagents

9-diazo-10-anthrone reacts with RMgX (R = Me, Et, Bu(n), 5-hexenyl, Pr(i), benzyl, Bu(t)) essentially yielding 9-alkylazo-10-hydroxy derivatives, which are isolated in their tautomeric quinoid structure as alkylhydrazones of 9,10-anthraquinone. The yields of these compounds decrease as the oxidation potentials (E(OX) of the Grignards decrease: at the same time additional compounds, formed through a radical mechanism, are obtained in higher yields. The reaction has been interpreted as a competition between single electron transfer (SET) and nucleophilic attack, which occur with ratios varying with the oxidation potentials of the Grignard reagents. Evidences for the SET pathway have been found performing an experiment in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a scavenger of C-centered radicals.

Products and Mechanism of the Oxidation of 9-Methylanthracene by Peroxydisulfate. Proton Loss and Nucleophile Addition Reactions of the 9-Methylanthracene Radical Cation

The Cu(II)-S2O82- oxidation of 9-methylanthracene (1) was studied in refluxing CH3CN/acetic acid and aqueous CH3CN.Side-chain and nuclear oxidation products and the dimeric compound lepidopterene (7) were produced.The lepidopterene was determined to be formed by the reaction of intermediate anthracenylmethyl cation with 1.In CH3CN/H2O nuclear oxidation products, 10-hydroxy-10-methyl-9-anthrone (2) and 10-methylene-9-anthrone (3) and dimer 7 were produced, with the nuclear products predominating.In CH3CN/HOAc the dimer and side-chain substitution products, 1-OAc (5a) and 1-NHAc (5c), were predominant over the nuclear products, which consisted mainly of 3 and 10-acetoxy-9-methylanthracene (4a).A mechanism is proposed where the initially formed radical cation undergoes competing proton loss and reversible nucleophile addition reactions to form respectively the anthracenylmethyl radical and nucleophile adduct radicals.Oxidation of the radicals by Cu(II) or S2O82- yield the corresponding cations that react to form the products 4,5, and 7.Compounds 2 and 3 form by subsequent oxidation of the nuclear oxidation product, 10-methyl-9-anthrol.The results suggest that nucleophile addition is faster than proton loss and that it is more reversible in CH3CN/HOAc than in CH3CN/H2O

Transannular Ozonides of 9-Alkoxyanthracenes

Ozonation of 9-alkoxyanthracenes in methanol at -78 deg C leads to transannular ozonides 7, most of which can be isolated in crystalline form.On warming in CH2Cl2, ozonides 7 undergo around -30 deg C a decomposition with O2 release leading mainly to 10-alkoxy-9-anthrones 8.The radical character of this decomposition is established, in the case of 9-methoxy-10-methylanthracene ozonide (7e), by adding H donors such as 2,4,6-tri-tert-butylphenol or hydroquinone, which direct the process toward formation of 10-hydroperxy-10-methyl-9-anthrone (2a).