cas 13076-29-4, 1,4-DIMETHOXYANTHRACENE | Articles data

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Conversion of Alkoxy-9,10-anthraquinones to Alkoxyanthracenes
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Shyamasundar, Nagaraj,Caluwe, Paul
p. 809 - 811
(1981)
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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.
Lu, Lingang,Chen, Qiyin,Zhu, Xiaozhang,Chen, Chuanfeng
p. 2464 - 2466
(2003)
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Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines
A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]-benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3- [2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2] benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC50 values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 μM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 μM range.
Hua, Duy H.,Tamura, Masafumi,Huang, Xiaodong,Stephany, Heidi A.,Helfrich, Brian A.,Perchellet, Elisabeth M.,Sperfslage, Bonnie J.,Perchellet, Jean-Pierre,Jiang, Suping,Kyle, Dennis E.,Chiang, Peter K.
p. 2907 - 2912
(2002)
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Carbon-13 NMR Spectroscopic Study of Substituted Anthracene Dications
A series of substituted anthracenes (2-10 and 20-21) were oxidized by SbF5/SO2ClF at 0 to -30 deg C to their dications (11-19 and 22-23), which were observed by carbon-13 NMR spectroscopy.In the studied anthracene dications substantial positive charge was found to be localized at C9 and C10 positions.Methyl substitution in these dications was found to deshield the α-carbons as compared to their shielding effect in the corresponding monocations.The proportionality factor of (13)C chemical shift to electron density was found to be 174.1-217.0 ppm/e-, clearly proving the dicationic nature of the ions.
Olah, George A.,Singh, Brij P.
p. 4830 - 4835
(1983)
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Clip[5]arenes: A new family of molecular clips
Here we report the design and syntheses of two new triptycene-based rigid acyclic C-shaped hosts, clip[5]arenes C[5]OH and C[5]ME, and the strong host–guest complexation between C[5]OH and an electron-poor bipyridinium salt, paraquat G. The Ka value for the host–guest complex C[5]OH ? G was calculated to be (1.09 ± 0.36) × 105 M?1 in acetone by using a non-linear curve-fitting method based on the UV–vis absorption titration experiments. Furthermore, based on this new host–guest recognition motif, a novel pseudopolyrotaxane-like supramolecular structure was constructed with C[5]OH threaded on polyviologen polymer VP-10.
Shi, Bingbing,Li, Zhengtao,Liu, Yuezhou,Shangguan, Liqing,Zhu, Huangtianzhi,Ju, Huaqiang,Huang, Feihe
p. 3477 - 3480
(2018)
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Synthesis, isolation, and characterization of Diels-Alder adducts between 1,4-dialkoxyanthracenes and maleic anhydride
In the Diels-Alder reaction of 1,4-dialkoxyanthracenes and maleic anhydride, which can afford syn- and anti-cycloadducts, the bridgehead methine proton of the cycloadducts has proved to be a useful probe for determining syn/anti selectivity, as supported by isolation of diastereomers, 1H NMR spectroscopy, and X-ray analysis. In the case of methoxy and propoxy substituents, a slight anti-preference was observed, on the other hand, the reaction of 1,4-bis(benzyloxy)anthracene gave a small syn-preference. Theoretical calculations of transition states of 1,4-dimethoxyanthracene and maleic anhydride showed no stereochemical preference. From UV-vis spectra, the formation of charge transfer complexes of anthracenes and maleic anhydride is possible.
Kitamura, Chitoshi,Hasegawa, Munehiro,Ishikawa, Hiroshi,Fujimoto, Jun,Ouchi, Mikio,Yoneda, Akio
p. 1385 - 1393
(2007/10/03)

The reaction of triptycene haloquinones with alkoxides. An unusual route to pentiptycene quinones
Triptycene haloquinones 3 react with sodium alkoxides in refluxing alcohol to afford, besides the expected substitution products, pentiptycene quinone 4. This approach to 4 is compared with a Diels-Alder strategy to the same compound.
Spyroudis, Spyros,Xanthopoulou, Nikoletta
p. 3767 - 3770
(2007/10/03)

Triptycene analogs
This invention provides analogs of triptycene which are useful as anticancer drugs, as well as for other uses. The potency of these compounds is in a similar magnitude as daunomycin, a currently used anticancer drug. Each compound of the invention produces one or more desired effects (blocking nucleoside transport, inhibiting nucleic acid or protein syntheses, decreasing the proliferation and viability of cancer cells, inducing DNA fragmentation or retaining their effectiveness against multidrug-resistant tumor cells).
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(2008/06/13)

Intramolecular electron transfer between terminal 1,4-dimethoxybenzene units in radical cations with a [2.2](1,4)naphthalenophane, [2.2](1,4)anthracenophane, and pentacene skeleton
Various radical cations, in which two terminal 1,4-dimethoxybenzene units are anellated to [2.2]paracyclophane (2b?+, 3b?+), [2.2](1,4)naphthalenophane (4d?+), and anthracene bridges (5?+), have been studied by ESR and ENDOR spectroscopy. In the syn- and anti-naphthalenophane radical cations 2b?+ and 3b?+ the delocalization of the unpaired electron over both π-moieties and the distinct difference between the first and second oxidation potentials, ΔE = E20 - E10 are evidence for a substantial intramolecular electronic interaction between the two electrophores. Extension of the bridge in 4d?+ and 5 by benzo anellation results in a localized radical cation. Strong intramolecular electronic interaction between the two electrophores is found in the 1,4,8,11-tetramethoxy-pentacene radical cation (5?+). The syntheses of 4d are described.
Wartini, Alexander R.,Staab, Heinz A.,Neugebauer, Franz A.
p. 1161 - 1170
(2007/10/03)

Phase-transfer Catalysis under Reductive Conditions: Hydroquinone Dialkyl Ethers from Quinones
Hydroquinone ethers with alternant and nonalternant topology are prepared in one-pot reactions from the corresponding quinones by using sodium dithionite, sodium hydroxide, and alkylating reagents under phase-transfer conditions (Adogen 464).The use of allyl bromide leads to O- and C-allylation.
Seitz, Ulrich,Daub, Joerg
p. 686 - 689
(2007/10/02)

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.
Quast, Helmut,Fuchsbauer, Hans-Lothar
p. 1016 - 1038
(2007/10/02)

N.M.R. Spectra and Conformations of 9,10-Dihydroanthracenes
The preparation of a series of substituted 9,10-dihydroanthracenes is described and their proton n.m.r. spectra are dicussed.It is suggested that the trans-isomers of 9,10-dialkyl-9,10-dihydroanthracenes, substituted in the 9,10- or peri-positions adopt a polar ring conformation with the 9,10-dialkyl substituents placed over the ring.It is further suggested that the highfield signal of the β-protons of the 9,10-dialkyl substituents is due to partly to the magnetic anisotropy of the aromatic rings, and partly to the magnetic anisotropy of the carbon-carbon bonds from the alkyl groups to the 9- and 10-positions in the central ring.
Ahmad, Naseer-ud-din,Cloke, Christopher,Hatton, Ian K.,Lewis, Norman J.,MacMillan, Jake
p. 1849 - 1858
(2007/10/02)

Dimeric naphthoquinones, III. - Note on the monoalkylation of 1,4-anthracenediol; Synthesis of quinizarine monoalkyl ethers
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Laatsch
p. 814 - 818
(2007/10/02)