• Title/Summary/Keyword: 2,5-Dihydrofuran

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Stereoselective Synthesis of Farnesol (Farnesol의 입체선택적 합성)

  • Dong-Soo Shin
    • Journal of the Korean Chemical Society
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    • v.36 no.4
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    • pp.579-583
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    • 1992
  • Stereoselective synthesis of farnesol, (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-tiren-1-ol(1), was carried out using 5-bromo-2-methylpent-2-ene(2) as a starting material. After conversion of 5-bromo-2-methylpent-2-ene(2) to the corresponding iodide compound, 5-(4-methylpent-3-enyl)-2,3-dihydrofuran(4) was obtained by alkylation of 5-lithio-2,3-dihydrofuran with 5-iodo-2-methylpent-2-ene. Ni(0)-catalyzed coupling reaction of the dihydrofuran 4 with MeMgI was proceeded to give (3E)-4,8-dimethylnona-3,7-dien-1-ol(5) in 72% yield. The resultant homoallylic alcohol 5 was converted to the (5E)-6,10-dimethylundeca-5,9-dien-2-one(8) in 4 steps. Compound 8 was condensed with dimethylmethoxycarbonylmethylphosponate in benzene follwed by $NaBH_4$ reduction in EtOH to yield (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol(1). Ni(0)-catalyzed coupling reaction of MeMgI with dihydrofuran 4 was a key step in this synthesis of farnesol(1).

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Component Analysis of Softwood Vinegar (침엽수 목초액의 성분분석)

  • ;;;Sano Yoshihiro
    • Journal of Korea Foresty Energy
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    • v.20 no.1
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    • pp.28-34
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    • 2001
  • To analyze chemical compositions of softwood vinegar prepared with continuous carbonized kiln, the chemical compositions were analyzed by GC-MS spectrometry. The results were summarized as follow : 1. The amounts of methylalcohol and acetic acid and of vinegar were 0.12% and 0.8% respectively, and acidity was 0.85 2. Perfume components of vinegar were frufual, 5-meayl-2-furancarboxyaldehyde, 2,3-pentanedione, 2-butanol, 2,3-dihydrofuran, 1-(2-furanyl)-etanone, benzaldehyde, 2-furan carboxyaldehyde and acetic acid. 3 Vinegar prepared from softwood, so that murk amount of guaiacyl compound and phenol derivetives are produced from lignin and extractives was analγzed. 4 The yield of 4-methyl-di-tert-butylphenol was the highest in the nutural and carbonyl and acetic acid in the acid fractions, 3-ethylpentane in the basic fraction, and guaiacol in the phenolic fraction.

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AgBF4/[Bmim]BF4-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans

  • Xia, Likai;Lee, Yong-Rok;Kim, Sung-Hong;Lyoo, Won-Seok
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1554-1558
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    • 2011
  • A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF$_4$/[Bmim]BF$_4$-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.

Synthesis of 1,2,3,4-Tetrahydroquinolines Using AlCl3 in Aqua Mediated

  • Behbahani, Farahnaz K.;Ziaei, Parisa
    • Journal of the Korean Chemical Society
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    • v.58 no.1
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    • pp.44-48
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    • 2014
  • Catalytic performance of Lewis acids have been investigated in the synthesis of 1,2,3,4-tetrahydroquinolines via cyclocondensation reaction of aniline derivatives with cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran. The catalytic activity of various of these catalysts in different solvents was compared with other classical catalysts such as KSF clay (1.5 g), $InCl_3$ (10-20 mol%), $ZrOCl_2$ (10 mol%), $Sc(OTf)_3$ (3 mol%), PANI-$InCl_3$ (10 mol%), $I_2$ (20 mol%), $InCl_3$ (5 mol%), 4-npa (25 mol%) and Cellulose-$SO_3H$ (0.03 g).

Inhibitory Activity of Diacylglycerol Acyltransferase by Tanshinones from the Root of Salvia miltiorrhiza

  • Ko, Jeong-Suk;Ryu, Shi-Young;Kim, Young-Sup;Chung, Mi-Yeon;Kang, Jong-Seong;Rho, Mun-Chual;Lee, Hyun-Sun;Kim, Young-Kook
    • Archives of Pharmacal Research
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    • v.25 no.4
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    • pp.446-448
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    • 2002
  • The inhibitory activity of tanshinones from Salvia miltiorrhiza was tested on rat liver diacylglycerol acyltransferase (DGAT). Cryptotanshinone (1) and 15,16-dihydrotanshinone I (3) exhibited potent DGAT inhibitory activities dose-dependently with $IC_{50}$ values of $10.5 {\;}{\mu\textrm{g}}/ml{\;}and{\;}11.1{\;}{\mu\textrm{g}}/ml$. However, tanshinone IIA (2) and tanshinone I (4) showed very weak inhibition ($IC_{50}{\;}value:{\;}>{\;}250{\;}{\mu\textrm{g}}/ml$). A dihydrofuran moiety was seemed to be responsible for the stronger inhibitory activity

Heterocyclic Nonlinear Optical Chromophores Composed of Phenothiazine or Carbazole Donor and 2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran Acceptor

  • Cho, Min-Ju;Kim, Ja-Youn;Kim, Jae-Hong;Lee, Seung-Hwan;Dalton, Larry R.;Choi, Dong-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.26 no.1
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    • pp.77-84
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    • 2005
  • We prepared the new nonlinear optical chromophores that show fairly high microscopic nonlinearity through intramolecular charge transfer. Phenothiazine and carbazole units played an important role to contribute high electron donability and connect the resonance pathway via conjugative effect in the cyclized ring beside the aromatic ring. Theoretical calculation, electrochemical analysis, and absorption spectroscopic study gave us useful information about the energy states and microscopic nonlinearities of two serial chromophores. We compared the microscopic nonlinearities of four chromophores with the conjugation length and electron donability in the push-pull type NLO chromophores. The effect of gradient donability and lengthening the conjugation were investigated on the electronic state and microscopic nonlinearity.

Theoretical Study of Solvent Effect on Yield of Oxidative Addition Reaction (산화첨가반응의 수득률에 미치는 용매효과에 관한 이론적 연구)

  • Lee, Chul-Jae;Kim, Byung-So
    • Applied Chemistry for Engineering
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    • v.21 no.5
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    • pp.586-589
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    • 2010
  • In present work, oxidative addition reaction of 1,3-cycleohexandion (1,3-CHD) with ethyl vinyl ether (EVE) was attempted utilizing $Ag_2CO_3$/celite (SC) reagent. In order to optimize reaction conditions, we surveyed several solvents for the production of dihydrofuran with the (SC) system. The yield of the acetonitrile (AN), dimethyl sulfoxide (DMSO), benzene (BZ), and heptane (HT) are given 78, 40, 15, and 10%, respectively. Therefore, we studied the solvent effects on yields by using PM3 and ZINDO/1 parameter of semi-empirical method of HyperChem7.0 molecular modeling program.