• Title/Summary/Keyword: epoxide

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Cobalt(III) Complexes of Various Salen-Type Ligand Bearing Four Quaternary Ammonium Salts and Their Reactivity for CO2/Epoxide Copolymerization

  • Kim, Bo-Eun;Varghese, Jobi Kodiyan;Han, Yong-Gyu;Lee, Bun-Yeoul
    • Bulletin of the Korean Chemical Society
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    • v.31 no.4
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    • pp.829-834
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    • 2010
  • Ligand variation was carried out on a cobalt(III) complex of Salen-type ligand comprised of 1,2-cyclohexenediamine and salicylaldehyde bearing a methyl substituent on 3-position and -[$CMe(CH_2CH_2CH_2N^+Bu_3)_2$] on 5-position, which is a highly active catalyst for $CO_2$/propylene oxide copolymerization. Replacement of the methyl substituent with bulky isopropyl group resulted in alteration of the binding mode, consequently lowering turnover frequency significantly. Replacement with an ethyl group preserved binding mode and activity. Replacement of the tributylammonium unit with trihexylammonium or trioctylammonium, or replacement of 1,2-cyclohexenediamino unit with -$NC(Me)_2CH_2N$- decreased activity, even though the binding mode was unaltered.

The Effect of Scoparone on the Hepatic Bromobenzene Metabolizing Enzyme System in Rats (간의 Bromobenzene 대사계에 미치는 Scoparone의 효과(I))

  • Kim, Eun-Ju;Lee, Chung-Kyu;Choi, Jong-Won
    • Korean Journal of Pharmacognosy
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    • v.23 no.2
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    • pp.81-88
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    • 1992
  • The effects of scoparone, one of coumarin derivative on the hepatic bromobenzene metabolizing enzyme system was estimated in rats. Scoparone pretreatment revealed dose-dependently the recovery of decrease in epoxide hydrolase activity due to the bromobenzene(310 mg/kg, i.p.) treatment. And also scoparone and scopoletin (each 5mg/kg, p.o.) pretreatments showed two times increase in the $V_{max}$ values compared to those of bromobenzene-treated group which were calculated from tripartite reciprocal plots. The mode of protective effect of scoparone against bromobenzene induced toxicity is considered to be due to the induction of microsomal enzyme activity by scopoletin, the intermediate metabolite of scoparone. The changes in cytochrome P-450 activity, aminopyrine N-demethylation, aniline hydroxylation and glutathione S-transferation in scoparone-treated group were not significantly different from those of the control group.

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Product Studies by HPLC on the Hydrolysis of the anti- and syn-Tetrahydrodiol Epoxides and the 1,2-Tetrahydro Epoxide of Naphthalene

  • 이용태;Jed F. Fisher
    • Bulletin of the Korean Chemical Society
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    • v.18 no.8
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    • pp.856-860
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    • 1997
  • The arene epoxides from naphthalene, 1β,2α-dihydroxy-3α,4α-epoxy- (1) and 1β,2α-dihydroxy-3β,4β-epoxy-1,2,3,4-tetrahydronaphthalene (2) (anti- and syn-diol epoxide), 1,2-epoxy-1,2,3,4-tetrahydronaphthalene (3), and 1,2-epoxy-l,2-dihydronaphthalene (4), are model compounds of the ultimate carcinogenic metabolites of polycyclic aromatic hydrocarbons, ubiquitous environmental pollutants which may be causal in several human cancers. The product distribution in the hydrolysis of 1-4 have been studied by HPLC analysis of reaction mixtures. The yields of the trans product from the hydronium-ion-catalyzed and pH-independent hydrolysis in 9 : 1 (v/v) 20 mM buffer-dioxane at 25 ℃, respectively, were; 1: 98, 100; 2: 74, 87, 3: 95, 97, 4:100, 100. The results were rationalized by conformational equilibria of the epoxides and the carbocationic and zwitterionic intermediates from the epoxides.

Formal Synthesis of Sex Pheromone of Gypsy Moth (+)-Disparlure from L-(+)-Tartaric Acid

  • Gi Baek Gwon;Hang Soo Kim;Jae Won Park;Jong Soo Choi;Kyung Oh Doh;Kyung Jin Kim;Young Bae, Seu
    • Journal of the Korean Chemical Society
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    • v.68 no.3
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    • pp.131-134
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    • 2024
  • A simple strategy for the formal synthesis of the sex pheromone of gypsy moth (+)-disparlure from L-(+)-tartaric acid is described herein. The key steps include the mono-esterification and regioselective ring-opening of an epoxide using a Grignard reagent. The strategy of conferring asymmetry using 2-butanone enables mono-esterification in high yield and reduces the number of steps. Subsequently, (+)-disparlure is synthesized via the regioselective ring opening of the epoxide.