• Title/Summary/Keyword: cyclohexene

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Catalytic Oxidation of Cyclohexene with Hydrogen Peroxide over Cu(II)-Cyclam-SBA-16 Catalyst

  • Prasetyanto, Eko Adi;Park, Sang-Eon
    • Bulletin of the Korean Chemical Society
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    • v.29 no.5
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    • pp.1033-1037
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    • 2008
  • A copper cyclam-type complex was successfully immobilized onto mesoporous silica SBA-16. Characterization by NIR spectroscopy and TGA analysis confirmed that copper cyclam complex is immobilized onto mesoporous SBA-16. The Cu(II)-Cyclam-SBA-16 was proven to be a good catalyst for oxidation reaction of cyclohexene with conversion up to 77.8% after 13 h reaction and providing a high selectivity to cyclohexenol and 3-hydroperoxycyclohex-1-ene. The results suggest that the copper species play a major role as catalyst via reversible redox cycles as proven by cyclic voltammetry analysis.

Synthesis and Exploratory Photochemistry of ${\beta},\;{\gamma}$-unsaturated Carboxylic Acid, Carboxamide and Nitrile Derivatives (${\beta},\;{\gamma}$-불포화카르복시산, 카르복시아미드와 니트릴 유도체의 합성과 이들의 광화학적 반응에 관한 연구)

  • Givens Richard S.;Woo Ki Chae
    • Journal of the Korean Chemical Society
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    • v.26 no.2
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    • pp.99-106
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    • 1982
  • The ketone chromophore of 1-Acetyl-1-methyl-2-cyclopentene (1) was replaced by nitrile, carboxylic acid and acetamide group, and their photochemical reactions were investigated. While the ${\beta},\;{\gamma}$-unsaturated ketone 1 afforded 1,2 ar 1,3-Acyl shift product, these replaced chromophores did not afford any monomeric rearranged products. 1-Cyano-1-methyl-2-cyclohexene also afforded no product anology of the 1,2-acyl shift reaction. The replacement of the ketone chromophore by nitrile, carboxylic acid and carboxamide has greatly altered the photochemistry of ${\beta},\;{\gamma}$-unsaturated ketones.

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Cytotoxic C-Benzylated Chalcone and Other Constituents of Ellipeiopsis cherrevensis

  • Wirasathien, Lalita;Pengsuparp, Thitima;Moriyasu, Masataka;Kawanishi, Kazuko;Suttisri, Rutt
    • Archives of Pharmacal Research
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    • v.29 no.6
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    • pp.497-502
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    • 2006
  • A new natural C-benzylated chalcone, $2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6{\c}-methoxychalcone$ (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCl-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with $IC_{50}$ values of 1.40, 5.31 and $13.92\;{\mu}g/mL$, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an $IC_{50}$ value of $7.1\;{\mu}g/mL$ as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.

Novel Syntheses of Isomers of Damascenone from Ethyl 2,6,6-Trimethyl-4-oxo-2-cyclohexene-1-carboxylate

  • Lee, Woo-Young;Jang, Se-Young;Lee, Jun-Gu;Chae, Woo-Ki
    • Bulletin of the Korean Chemical Society
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    • v.12 no.1
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    • pp.31-35
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    • 1991
  • Three isomers of damascenone, odorous terpenic ketones, have been synthesized conveniently from a same starting material, ethyl 2,6,6-trimethyl-4-oxo-2-cyclohexene-1-carboxylate(1), which was easily available by the acid-catalyzed condensation of mesityl oxide or acetone with ethyl acetoacetate. ${\alpha}$-Damascenone(7) was prepared by converting the enone ester 1 into the corresponding tosylhydrazone(4), followed by treating with 4 molar equiv of allyllithium. ${\beta}$-Damascenone(12) was synthesized by chemoselective reduction of 1 with sodium borohydride/cerium chloride to give corresponding allylic alcohol 8, conversion of 8 into acetate 9, and thermal decomposition of 9 with DBU to afford ethyl ${\beta}$-safranate(10), followed by reaction with an excess amount of allyllithium. ${\gamma}$-Damascenone(15) was obtained by dehydration of 8 with boric acid to furnish ${\gamma}$-safranate(13), followed by treatment with 2 molar equiv of allyllithium.

Fermi Resonance and Solvent Dependence of the νC=O Frequency shifts of Raman Spectra: Cyclohecanone and 2-Cyclohexen-1-one

  • Nam, Sang Il;Min, Eun Seon;Jeong, Yeong Mi;Lee, Mu Sang
    • Bulletin of the Korean Chemical Society
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    • v.22 no.9
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    • pp.989-993
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    • 2001
  • The carbonyl stretching vibration, νC=O of 2-cyclohexene-1-one, is in Fermi resonance with a combination tone. The amount of Fermi resonance interaction between these two modes is dependent upon the amount of solute/solvent interaction due to hyd rogen bonding between the carbonyl oxygen and the solvent proton. The corrected νC=O frequency of 2-cyclohexene-1-one occurs at a lower frequency than the observed νC=O mode of cyclohexanone, possibly caused by expanded conjugation effects. The carbonyl stretching modes of cyclic ketones were also affected by interaction with the ROH/CCl4 mixed solvent system.

Cytotoxic constituents of Zingiber cassumunar

  • Han, Ah-Reum;Kim, Hyang-Rim;Min, Hye-Young;Windono, Tri;Jeohn, Gwang-Ho;Lee, Sang-Kook;Seo, Eun-Kyoung
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.66.2-66.2
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    • 2003
  • A new phenylbutenoid dimmer, ( )-trans-3-(3'-methoxy-4'-hydroxyphenyl)- 4- [(E)- 3',4'-dimethoxystyryl] cyclohexene (1), were isolated from the rhizomes of Zingiber cassumunar along with three known phenylbutenoids, ( )-trans-3-(3', 4'- dimethoxyphenyl)-4-[(E)-3'",4"'-dimethoxystyryl]cyclohexene (2), 4-(3' ,4'- dimethoxyphenyl)but-1,3-diene (3) , and 4-(2',4',5'-trimethoxy-phenyl)but-1,3-diene (4), and a known heptanoid, curcumin (7), as cytotoxic constituents against several human cancer cell lines. (omitted)

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Ring-Opening Polymerization of $\varepsilon$-Caprolactone and Cyclohexene Oxide Initiated by Aluminum $\beta$-Ketoamino Complexes: Steric and Electronic Effect of 3-Position Substituents of the Ligands

  • Liu, Binyuan;Li, Haiqing;Ha, Chang-Sik;Kim, Il;Yan, Weidong
    • Macromolecular Research
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    • v.16 no.5
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    • pp.441-445
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    • 2008
  • A series of aluminum complexes supported by $\beta$-ketoamino, ligand-bearing, 3-position substituents $LAlEt_2$ ($L=CH_3C(O)C(Cl)=C(CH_3)NAr\;(L_1)$, $L=CH_3C(O)C(H)=C(CH_3)NAr\;(L_2)$, $L=CH_3C(O)C(Ph)=C(CH_3)NAr\;(L_3)$, and $L=CH_3C(O)C(Me)=C(CH_3)NAr\;(L_4)$, $Ar=2,6-^iPr_2C6H_3$) were synthesized in situ and employed in the ring-opening polymerization (ROP) of $\varepsilon$-caprolactone ($\varepsilon$-CL) and cyclohexene oxide (CHO). The 3-position substituents on the $\beta$-ketoamino ligand backbone of the aluminum complexes influenced the catalyst activity remarkably for both ROP of $\varepsilon$-CL and CHO. Aluminum $\beta$-ketoamino complexes displayed different catalytic behavior in ROP of $\varepsilon$-CL and CHO. The order of the catalytic activity of $LAlEt_2$ was $L_1AlEt_2$>$L_2AlEt_2$>$L_3AlEt_2$>$L_4AlEt_2$ for ROP of $\varepsilon$-CL, being opposite to the electron-donating ability of the 3-position substituents on the $\beta$-ketoamino ligand, while the order of the catalytic activity for ROP of CHO was $L_1AlEt_2$>$L_3AlEt_2$>$L_4AlEt_2$>$L_2AlEt_2$. The effects of reaction temperature and time on the ROP were also investigated for both $\varepsilon$-CL and CHO.