• Title/Summary/Keyword: Cyclopentanone

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Studies on the Synthesis of Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione (Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione의 합성)

  • Ui Chun Chong;Sae Hee Chang;K.V. Scherer, Jr.
    • Journal of the Korean Chemical Society
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    • v.18 no.6
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    • pp.437-442
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    • 1974
  • Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione was synthesized from the cyclopentanone in good overall yield(60%). Cyclopentanone ethylene ketal(Ⅰ) was brominated with pyridinium bromide perbromide, and the brominated ketal(Ⅱ) was converted to the dimer of cyclopentadienone ethylene ketal(Ⅲ). The ethylene ketal(Ⅲ) was again converted to the dicyclopentadiene-1,8-dione(Ⅳ). Finally, the pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione(Ⅴ) was synthesized from the dicyclopentadilene-1,8-dione(Ⅳ) by photochemical cyclization.

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Synthesis and Absorption Spectral Properties of Bis-methine Dyes Exemplified by 2,5-Bis-arylidene-1-dicyanomethylene-cyclopentanes

  • Asiri, Abdullah Mohamed
    • Bulletin of the Korean Chemical Society
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    • v.24 no.4
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    • pp.426-430
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    • 2003
  • A range of methine dyes has been synthesized by condensation of highly electronegative active methylene compound dicyanomethylenecyclopentane derived from cyclopentanone with the formyl group of substituted benzaldehydes. The electronic absorption spectroscopic properties of the dyes were investigated. In general, substituents on the aromatic aldehyde moiety have a significant effect on the visible absorption maxima of the dyes; increasing the solvent polarity also showed a pronounced effect on the absorption maxima.

Palladium Dichloro Complex Catalysed Oxidation of Cyclopentene by Dioxygen in Tetralin$^\dag$

  • Takehira, Katsuomi;Hayakawa, Takashi;Orita, Hideo;Shimizu, Masao;Oh, In-Hwan
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.254-257
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    • 1987
  • Palladium dichloro complexes catalysed the oxidation of cyclopentene by dioxygen in tetralin solvent at ambient temperature. Cyclopentanone formed mainly together with autoxidation products from both cyclopentene and tetralin. The oxidation seems to proceed by co-oxidation mechanism, where tetralin was first oxidized to its hydroperoxide which then oxidized cyclopentene to cyclopentanone. Mechanism of the other by-products formations has been discussed.

Studies on the Semicarbazone Formation of Aliphatic and Alicyclic Ketones. (Aliphatic Ketone과 Alicyclic Ketone의 Semicarbazone 생성반응에 관한 연구)

  • Lim, Nag-Bin;Oh, Yang-Hwan;Kim, Yong-In
    • Journal of the Korean Applied Science and Technology
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    • v.8 no.1
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    • pp.59-67
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    • 1991
  • The reactions of semicarbazide hydrochloride with aliphatic and alicyclic ketones were studied kinetically at 15, 25, 35 and 45$^{\circ}C$ in 20% ethanol solution buffered at pH 2.9. The rate of cyclohexanone semicarbazone formation is 5.5 times as fast as that of cyclopentanone semicarbazone, while 3-pentanone semicarbazone is 4.7 times as slow as that of 2-pentanone, The activation energy of cyclohexanone, 2-pentanone, 2 hexanone, cyclopentanone, 4-methyl-2-pentanone and 3-pentanone semicarbazone formation are calculated 5.08, 7.52, 8.79, 9.59, 9.49, 11.59, respectively. It is concluded from the effect of ionic strength that the reaction is affected by not ion but neutral molecules being progressed hydrogen bond between oxygen atom of carbonyl group and hydrogen atom of acid-catalyst and concerted nucleophilic attack of free base on the carbonly compound. Dependence on pH of the rate of 2-pentanone semicarbozone formation is linear relationship below pH 4.60 and above pH 5.60. As a result of studing citric acid catalysis, second order constants increase linearly with citric acid concentration. As the catalyst concentration is varied from 0.025 to 0.10 mol/1 at pH 2.90, the rate constants increase 1.4 times, but slight increase is observed at pH 5.60. Conclusively, the rate-determining step is formation of tetrahedral interemediate below pH 4.65 and dehydration between pH 5.60 and pH 7.11. It is concluded that the formation reaction of cyclohexanone semicarbazone is faster than cyclopentanone semicarbazone due to the steric strain in the process of forming tetrahedral intermediate.

Electric Field Induced Anisotropic Nonlinear Refractive Index of Organic Solution (전기장에 의한 유기용액의 비등방 비선형 굴절율)

  • 원영희;김용기;이종하;이현곤
    • Korean Journal of Optics and Photonics
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    • v.5 no.4
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    • pp.481-486
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    • 1994
  • We demonstrate z-scan method as a tool for investigating the molecular orientational order in organic solution when high static electric field is applied. Experiments are performed for the solution of 0.5% (by weight) 4-dimethylamino-4'-nitrostilbene in cyclopentanone and nonlinear refractive index $n_{2}$, is measured to be $-0.905\times10^{-8}\textrm{cm}^2/MW$ at $1.064{\mu}m$. When static electric field of 3.45 KV fmm is applied, the anisotropy ratio of n, is measured to be 1.34 and the molecular orientational order parameters $

    _2 and

    _4$ are found to be 0.092 and -0.128, respectively. ively.

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Synthesis of 2,5Bis(2'-piperidymethyl)piperidine and Related Compounds

  • Hammouda, Metwally;Kandeel, Ex-el-Din;Hamama, Wafaa;Afsah, Elsayed
    • Archives of Pharmacal Research
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    • v.16 no.1
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    • pp.68-70
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    • 1993
  • The triketones 3-6 were obtained by alkylation of cyclopentanone or cyclohexanone with the appropriate cycloalkanone bis-mannich base (1) or (2). Schmidt reaction of the tricketones 3-6 afforded the corresponding trcyclic lactames 7-10 respectively. reduction of 7 and 9 gave compounds 11 and 12 respectively.

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Two Phase Reduction of Carbonyl Compounds with Sodium Borohydride

  • Jin Soon Chong;Nung Min Yoon
    • Journal of the Korean Chemical Society
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    • v.15 no.3
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    • pp.117-120
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    • 1971
  • Possibility of two phase reduction of carbonyl compounds to the corresponding alcohols was studied. Thus the 0.5 M ether solutions of the representative carbonyl compounds were treated with alkaline stabilized sodium borohydride aqueous solution at room temperature. Butyraldehyde was reduced rapidly within one hr., whereas other aldehydes tested; heptaldehyde, benzaldehyde, and 1-naphthaldehyde were reduced in 6-12 hr. 2-Heptanone was reduced much slowly; 87% in 48 hr., however, acetophenone was reduced moderately; 92% in 12 hr. and cycloalkanones were reduced rapidly (cyclohexanone in 0.5 hr., and cyclopentanone in 3-6 hr.).

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Selective Reduction of Oximes to N-Monosubstituted Hydroxylamines with Lithium Borohydride

  • Cho, Byung-Tae;Seong, See-Yearl
    • Bulletin of the Korean Chemical Society
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    • v.9 no.5
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    • pp.322-324
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    • 1988
  • Selective reduction of aldoximes and ketoximes with lithium borohydride in tetrahydrofuran was investigated. Thus, aldoximes and cyclic ketoximes such as hexanaldoxime, heptanaldoxime, cyclopentanone oxime and cyclohexanone oxime were reduced smoothly to the corresponding N-monosubstituted hydroxylamines at room temperature in 65-93% yield. The reduction of alicyclic ketoxime was very slow, requiring somewhat high reaction temperature ($65^{\circ}C$) for the complete reduction to give the hydroxnylamines. The reduction of aromatic oximes such as benzaldoxime and acetophenone oxime was very sluggish, giving a mixture of the corresponding hydroxylamines and amines at $65^{\circ}C$.

The Synthesis of Chlorin-based Photosensitizers for using in Photodynamics Therapy by Modification of Methyl Pyropheophorbide-a

  • Wang, Jin-Jun;Han, Guang-Fan;Shim, Young-Key
    • Journal of Photoscience
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    • v.8 no.2
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    • pp.75-77
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    • 2001
  • The Grignard reaction of methyl pyropheophorbide-a (MPP-a) was performed to introduce lengthy alkyl chain for improving lipophilicity. After the introduction of alkyl chain to the both of carbonyls, peripheral aldehyde and cyclopentanone, the obtained diol 3 was subjected to dehydration to give monodehydrate product 4 selectively. The Qy band of prepared compounds were affected by the substituents on the Qy axis (N$\sub$21/-N$\sub$23/).

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Isolation and Characterization of Cyclohexanol-utilizing Bacteria (Cyclohexanol 이용성 세균의 분리 및 특성)

  • 김태강;이인구
    • Microbiology and Biotechnology Letters
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    • v.27 no.2
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    • pp.107-112
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    • 1999
  • A bacterium, which can utilize cyclohexanol as a sole source of carbon and energy, was isolated from sludge in sewage of Ulsan Industrial Complex for Petrochemicals, Korea and identified as Rhodococcus sp. TK6. The growth conditions of the bacteria were investigated in cyclohexanol containing media. The bacteria utilized cyclohexanol, cyclohexanone, cyclohexane-1,2=diol, cyclopentanol, cyclopentanone, and $\varepsilon$-caprolactone but not cyclohexane, cyclohexane-1,2-dione, and cyclooctanone. The bacteria were able to utilize alcohols such as ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-methyl-1-propanol, 3-methyl-1-butanol, 2-propanol, and 2-butanol as well as cyclohexanol, organic acids such as adipate, propionate, butyrate, valerate, n-caproate, and 6-hydroxycaproate, and aromatic compounds such as phenol, salicylate, p-hydroxbenzoate, and benzoate as a sole source of carbon and energy. Cyclohexanone as a degradation product of cyclohexanol by Rhodococcus sp. TK6 was determined with gas chromatography.

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