Metalloporphyrin-Catalyzed Oxidation of 2-Cycloalkyl-3-hydroxynaphthoquinones

Cunningham, Ian D.; Danks, Timothy N.; O'Connell, Keith.; Scott, Peter W.

doi:10.1021/jo990297n

Cited by 13 publications

(9 citation statements)

References 22 publications

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“…In the last two decades, oxidation of hydrocarbons catalyzed by metalloporphyrins under mild conditions has attracted much interest because of their potential application and the environmentally friendly conditions [21][22][23][24][25][26][27]. A large class of synthetic metalloporphyrins was used as catalysts for the oxidation of saturated C-H bond, C-C double bonds and aromatics [28][29][30][31][32][33][34][35]. Our group has reported that metalloporphyrins could catalyze effectively the oxidation of cyclohexane [36] and toluene [37] with air in the absence of any cocatalysts and reductant.…”

Section: Introductionmentioning

confidence: 99%

Catalysis of metalloporphyrins for selective hydroxylation of phenol by H₂O₂

Zeng

Jiang

Zhu

et al. 2006

J. Porphyrins Phthalocyanines

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Liquid phase catalytic selective hydroxylation of phenol to catechol and hydroquinone was carried out in the presence of metalloporphyrins using hydrogen peroxide as oxidant and water as solvent. Five kinds of metal tetra(p-chlorophenyl)porphrin (T(p-Cl)PPMCl, M = Fe, Co, Mn, Cu, Zn) were studied. It was found that T(p-Cl)PPFeCl had high catalytic activity and diphenol selectivity for the hydroxylation of phenol to catechol and hydroquinone. The influence of various reaction parameters, namely, reaction temperature, solvent, ratio of substrate and oxidant, substrate concentration, the amount of catalyst, reaction time and pH value were investigated systematically. When water was used as solvent (10 mL), the optimum conditions were following: pH = 7, the concentration of phenol was 0.3 g/mL, the molar ratio of phenol and H 2 O 2 was 1/2, the molar ratio of catalyst and phenol was 7/100000, the reaction temperature was 65 °C and the reaction time was 1.5 h. Under above optimum conditions, the phenol conversion was up to 55.1%, and the selectivity of diphenol was almost up to 99.9%, the molar turnover numbers of the catalyst was about 7500. A possible mechanism was also proposed.

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Section: Introductionmentioning

confidence: 99%

Catalysis of metalloporphyrins for selective hydroxylation of phenol by H₂O₂

Zeng

Jiang

Zhu

et al. 2006

J. Porphyrins Phthalocyanines

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“…[10] While the corresponding Gdm rearrangement is unprecedented, the analogous Hooker oxidation rearrangement of hydroxynaphthoquinones to indane carboxylic acids served as related precedent. [11] For this study, the synthesis of the Gdm model surrogate 2-hydroxyquinone 21 (Scheme 2) commenced with aryl lithiation–alkylation of benzyl methyl ether 12 . DDQ-mediated oxidation of 13 followed by hydroxy-directed iodination provided phenol 15 .…”

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confidence: 99%

Mccrearamycins A–D, Geldanamycin‐Derived Cyclopentenone Macrolactams from an Eastern Kentucky Abandoned Coal Mine Microbe

et al. 2017

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Four cyclopentenone-containing ansamycin polyketides (mccrearamycins A–D), and six new geldanamycins (Gdms B–G, including new linear and mycothiol conjugates), were characterized as metabolites of Streptomyces sp. AD-23-14 isolated from the Rock Creek underground coal mine acid drainage site. Biomimetic chemical conversion studies using both simple synthetic models and Gdm D confirmed that the mccrearamycin cyclopentenone derives from benzilic acid rearrangement of 19-hydroxy Gdm, and thereby provides a new synthetic derivatization strategy and implicates a potential unique biocatalyst in mccrearamycin cyclopentenone formation. In addition to standard Hsp90α binding and cell line cytotoxicity assays, this study also highlights the first assessment of Hsp90α modulators in a new axolotl embryo tail regeneration (ETR) assay as a potential new whole animal assay for Hsp90 modulator discovery.

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“…Stirring lawsone 1 with H 2 O 2 in MeOH/CH 2 Cl 2 (3:1) for 90 min at r.t. afforded 2,3‐dihydroxynaphthalen‐1,4‐dione ( 339 ) (Scheme ).…”

Section: Reactivity Of Lawsonementioning

confidence: 99%