Dimere Naphthochinone, II. Einfache und regioselektive Synthese von Naphthohydrochinon‐monoalkylethern über 2,3‐Dihydronaphthochinone

Laatsch, Hartmut

doi:10.1002/jlac.198019800111

Cited by 46 publications

(28 citation statements)

References 22 publications

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“…[18][19][20] As reported by Kündig, [20] its 1 H (300 MHz, CDCl 3 ) spectrum contains three signals: 8.05-8.01 (m, 2H), 7.76-7.71 (m, 2H) and 3.08 ppm (s, 4H). In our case, interaction of I with 1-adamantanol in CF 3 COOH leads to formation of 2-(1-adamantyl)-2,3-dihydronaphthalene-1,4-dione (1).…”

Section: Resultsmentioning

confidence: 89%

Preparation of adamantyl derivatives of 1,4‐; 1,6‐ and 1,7‐dihydroxynaphthalenes and assignment of their NMR data

Peterson

Svirskaya

Kondrasenko

et al. 2013

Magnetic Reson in Chemistry

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Adamantylation of dihydroxynaphthalenes with the hydroxyl groups on the same or different rings leads to compounds that are convenient starting materials in target-oriented organic synthesis. Here, we report the (1)H and (13)C NMR assignments of eight 1-adamantyl substituted derivatives of 1,4-; 1,6- and 1,7-dihydroxynaphthalenes. The data acquired and peculiarities of their molecular structure are useful for extrapolation for prompt characterization of compounds containing adamantane, dihydroxynaphthalenes or naphthoquinone units.

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Section: Resultsmentioning

confidence: 89%

Preparation of adamantyl derivatives of 1,4‐; 1,6‐ and 1,7‐dihydroxynaphthalenes and assignment of their NMR data

Peterson

Svirskaya

Kondrasenko

et al. 2013

Magnetic Reson in Chemistry

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“…Therefore, meat extract medium was used for a 20 L culture at standard conditions [151] . After 10 days, the broth was extracted using XAD-16 for the super- (111) were recently described by us in detail [152] . A search with the discussed spectroscopic data and the molecular weight of 108…”

Section: Terrestrial Streptomyces Sp Bl 47/4455mentioning

confidence: 99%

“…Compound 71 was further synthesized by treatment of 1-hydroxy-4-methoxynaphthaline (71) with carbon dioxide/anhydrous potassium carbonate [110,111] . Based on NMR spectroscopy, both the synthetic and the natural acid differed in their 1 H and 13 C NMR shifts (Table 2).…”

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confidence: 99%

“…In accordance, a search in AntiBase referred to bafilomycin C 1 (112) as sole possible structure, which was further confirmed by a comparison with the literature [153,159] . Bafilomycin C 1 (112) was reported to exhibit higher [153] antibacterial activity than bafilomycins A 1 (108), A 2 (109), B 1 (110), and B 2 (111). Along with its insecticidal and immunosuppressive activity, bafilomycin C 1 (112) was reported as ATPase inhibitor.…”

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confidence: 99%

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A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…[13] The conversion of 1 into 2 can also be effected in neat CF 3 COOH. [14] The dione 8 has also been obtained by hydrogenation of naphthoquinone with Wilkinson's catalyst [15] and very recently by benzylic oxidation of tetrahydronaphthalene-I-one catalyzed by Rh 2 (cap) 4 . [16] The dione is kinetically stable at RT but rapidly converts to the phenolic form in the presence of base.…”

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confidence: 99%

Tetrahydronaphthalene-1,4-dione and its Chromiumtricarbonyl Complex

Garcia¹,

Kündig²,

Lomberget³

et al. 2007

Chimia

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The article gives a brief outline of the rediscovery of tetrahydronaphthalene-1,4-dione, a stable tautomer which has been known for over half a century but has not been applied in synthesis. Desymmetrization is readily achieved via enantioselective reduction. Synthetic potential apart, the dione and its chromiumtricarbonyl complex are of theoretical interest. Thus, whereas dihydroxynaphthalene requires quite harsh conditions and leads to a 1:1 mixture of the two tautomers, the chromiumtricarbonyl complex of dihydroxynaphthalene tautomerizes under very mild conditions to the tetrahydronaphthalene-1,4-dione complex. An earlier literature report showed that in trifluoroacetic acid, the dione tautomer is present exclusively. This has now been used to isolate multigram quantities of the compound

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Dimere Naphthochinone, II. Einfache und regioselektive Synthese von Naphthohydrochinon‐monoalkylethern über 2,3‐Dihydronaphthochinone

Cited by 46 publications

References 22 publications

Preparation of adamantyl derivatives of 1,4‐; 1,6‐ and 1,7‐dihydroxynaphthalenes and assignment of their NMR data

Preparation of adamantyl derivatives of 1,4‐; 1,6‐ and 1,7‐dihydroxynaphthalenes and assignment of their NMR data

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Tetrahydronaphthalene-1,4-dione and its Chromiumtricarbonyl Complex

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