• Title/Summary/Keyword: vinyl ketones

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A Practical Synthesis of Morita-Baylis-Hillman Adducts of Aryl Vinyl Ketones Catalyzed by a Proton Donor

  • Kim, Sung-Hwan;Kim, Se-Hee;Lim, Cheol-Hee;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.6
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    • pp.2023-2027
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    • 2012
  • An efficient and practical synthesis of MBH adducts of aryl vinyl ketones was developed using DABCO and 4-nitrophenol as a proton donor. Addition of a proton donor and the use of excess amounts (3.0 equiv) of aldehydes were highly beneficial for the yields of MBH adducts of aryl vinyl ketones.

Palladium Catalyzed Carbonylative Vinylation of Aryl Halides with Olefins and Carbon Monoxide

  • Kim, Jin-Il;Ryu, Cheol-Mo
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.246-250
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    • 1987
  • The reaction of aryl iodides or bromides with olefins in the presence of 1 mol % of $PdCl_2(PPh_3)_2$ and 3 equiv. of $n-Bu_3N\; at\; 100^{\circ}C$ in carbon monoxide atmosphere gave the corresponding aryl vinyl ketones in good yields with small amount of vinylated 1-aryl olefins. But, when the reaction was proceeded under the 10 atm of carbon monoxide, aryl vinyl ${\alpha}$-diketones and aryl vinyl ketones were obtained in moderate to good yields. The reaction was tolerant of a wide variety of functional groups on either the aryl halides or olefin compounds. Reactivity of aryl halide decrease in the order; aryl iodide > aryl bromide ${\gg}$aryl chloride. In general, the reaction proceeded well and gave good yields of aryl vinyl ketones and aryl vinyl ${\alpha}$-diketones when reactants are substituted with electron withdrawing groups.

Mechanism and regulation of body malodor generation (2) -Development of a novel deodorant powder and application as an antiperspirant-

  • Miyazaki, M.;Fujihira, K.;Sadaie, M.;Nishikawa, N.;Kon, R.;Sugiyama, K.
    • Proceedings of the SCSK Conference
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    • 2003.09b
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    • pp.110-116
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    • 2003
  • We have developed a high performance powder, which has a quenching efficacy not only for short-chain fatty acids and amines, but also for vinyl ketones (l-octen-3-one, cis-l,5-octadien-3-one), newly found as other key compounds in axillary malodor. By investigating various powders known to have a quenching efficacy, we finally developed a highly porous silica bead containing magnesium oxide. We found that the superior deodorant effect performed by this powder was the result of multiple effects due to both an excellent physical adsorption capability from its high porosity and a specific adsorption of vinyl ketones by magnesium in the powder. An antiperspirant formulation containing both this powder and a Morus alba extract showed good efficacy as a deodorant.

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Mechanism and regulation of body malodor generation (1) -Effect of iron in axillary malodor and using an antioxidant as a deodorant-

  • Ichinose, N.;lida, S.;Gomi, T.;Someya, K.;Hirano, K.;Ogura, M.;Yamazaki, S.;Sakurai, K.
    • Proceedings of the SCSK Conference
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    • 2003.09b
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    • pp.139-144
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    • 2003
  • Using GC/MS and GC/Olfactmetry analysis, we identified two vinyl ketones such as 1-Octen-3-one (OEO) and cis-1, 5-Octadien-3-one (ODO) as key materials in axillary odor. OEO and ODO showed a strong metallic odor and low odor threshold. These two materials were occurred from the reaction of unsaturated long fatty acids in lipids and the iron ion in our body's metabolism. Then, it was recognized that Morus alba (Japanese name, Kuwa) extract, one of the plant extract, showed a very good effect to control the generation of these vinyl ketones due to its remarkable anti-oxidization effects.

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Syntheses of Alternating Head-to-Head Copolymers of Vinyl Ketones and Vinyl Ethers, and Their Properties. Ring-Opening Polymerization of 2,3,6-Trisubstituted-3,4-dihydro-2H-pyrans

  • Lee, Ju-Yeon;Cho, I-Whan
    • Bulletin of the Korean Chemical Society
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    • v.8 no.2
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    • pp.102-105
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    • 1987
  • 2-Methoxy-6-methyl-3,4-dihydro-2H-pyran ($1_a$), 2-ethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran ($1_b$), and 2-ethoxy-3-methyl-6-ethyl-3,4-dihydro-2H-pyran ($1_c$) were prepared by (4 + 2) cycloaddition reaction from the corresponding vinyl ketones and alkyl vinyl ethers. Compounds $1_{a-c}$ were ring-open polymerized by cationic catalyst to obtain alternating head-to-head (H-H) copolymers. For comparison, copolymer of head-to-tail (H-T) was also prepared by free radical copolymerization of the mixture of the corresponding monomers. The H-H copolymer exhibited some differences in its $^1H$ NMR and IR spectra. However, significant differences were showed between the H-H and H-T copolymers in the $^{13}C$ NMR spectra. Also noteworthy was that$T_g$ value of H-H copolymer was higher than that of the corresponding H-T structure. Decomposition temperature of the H-H copolymer was lower than that of the H-T copolymer. All the H-H and H-T copolymers were soluble in common solvents.

Catalytic and Stoichiometric Hydroacylation of Olefin Derivatives with 8-Quinolinecarboxaldehyde by Rh(I)

  • Jun, Chul-Ho;Han, Jong-Soo;Kang, Jung-Bu;Kim, Sun-Il
    • Bulletin of the Korean Chemical Society
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    • v.15 no.3
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    • pp.204-209
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    • 1994
  • Catalytic hydroacylation has been achieved by the reaction of 8-quinolinecarboxaldehyde (1) and various vinyl derivatives such as 2a, 2b and 2c with Wilkinson's complex (3) to give linear alkyl ketones, 4a, 4b and 4c, respectively. However, stoichiometric ligand-promoted hydroacylation of 2a and 2b with [$(C_8H_{14})_2RhCl]_2$ (5) resulted in a mixture of the branched alkyl ketones and the linear alkyl ketones in different ratios. Stoichiometric hydroacylation of some other olefin derivatives such as 6, 11, 12 and 26, produced functionalized alkyl ketone compounds.

Characterization of Volatile Compounds in Low-Temperature and Long-Term Fermented Baechu Kimchi (묵은 배추김치의 휘발성 성분 특성)

  • Kim, Ji-Yun;Park, Eun-Young;Kim, Young-Suk
    • Journal of the Korean Society of Food Culture
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    • v.21 no.3
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    • pp.319-324
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    • 2006
  • Volatile compounds in low-temperature and long-term fermented Baechu kimchi were extracted by high vacuum sublimation(HVS), and then analyzed by gas chromatography/mass spectrometry(GC-MS). A total of 62 compounds, including 7 sulfur-containing compounds, 8 terpenes, 5 esters, 8 acids, 15 alcohols, 2 nitrites, 2 ketones, 11 aliphatic hydrocarbons and 4 miscellaneous compounds, were found in low-temperature and long-term fermented Baechu kimchi. Among them, acetic acid and butanoic acid were quantitatively dominant. Aroma-active compounds were also determined by gas chromatography/olfactometry(GC-O) using aroma extract dilution analysis(AEDA). A total of 16 aroma-active compounds were detected by GC-O. Butanoic acid was the most potent aroma-active compound with the highest FD factor($Log_3FD$) followed by linalool, acetic acid, 2-vinyl-4H-1,3-dithin and 3-methyl-1-butanol. The major aroma-active compounds, such as acetic acid and butanoic acid, were related to sour and rancid or notes.

Formation of Fruit Aroma Compounds from Whey by Kluyverumyces lactis (Kluyveromyces lactis에 의한 유청으로부터 과일향 성분의 생성)

  • 김소미;이형주
    • Microbiology and Biotechnology Letters
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    • v.19 no.5
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    • pp.536-541
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    • 1991
  • To enhance the productivity of fruit flavor compounds from whey by the lactose fermenting yeast, Kluyveromyces lactzs ATCC 8585 was treated with N-methyI-N'-nitro-N-nitrosoguanidine (NTG). After the NTG treatments, a mutant showing resistance to antifungal activity of geraniol, and strong fruity but low yeasty flavor was selected and named as K. lactis 450 K. Flavor compounds from 3-day culture broth were extracted with pentane-dichloromethane (2:l) and the concentrated oleoresins were analyzed by gas chromatography. The mutant strain produced more classes and larger amount of flavor compounds than the parent stlain. Tentatively identified volatile compounds from the culture of the mutant were: terpenes such as myrcenol; alcohols such as cis-3-hexenol, n-hexanol; esters such as ethyl isovalerate, cis- 3-hexenyl n-butyrate, n-amyl-n-hexanoate, phenyl ethyl n-propioate; ketones such as methyl vinyl ketones; other compounds such as vanillin, 3-methylcoumarin.

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Electromagnetic Interference Shielding Properties of CO2 Activated Carbon Black Filled Polymer Coating Materials

  • Hu, Quanli;Kim, Myung-Soo
    • Carbon letters
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    • v.9 no.4
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    • pp.298-302
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    • 2008
  • Carbon blacks could be used as the filler for the electromagnetic interference (EMI) shielding. The poly vinyl alcohol (PVA) and polyvinylidene fluoride (PVDF) were used as the matrix for the carbon black fillers. Porous carbon blacks were prepared by $CO_2$ activation. The activation was performed by treating the carbon blacks in $CO_2$ to different degrees of burnoff. During the activation, the enlargement of pore diameters, and development of microporous and mesoporous structures were introduced in the carbon blacks, resulting in an increase of extremely large specific surface areas. The porosity of carbon blacks was an increasing function of the degree of burn-off. The surface area increased from $80\;m^2/g$ to $1142\;m^2/g$ and the total pore volume increased from $0.14073\;cc{\cdot}g^{-1}$ to $0.9343\;cc{\cdot}g^{-1}$. Also, the C=O functional group characterized by aldehydes, ketones, carboxylic acids and esters was enhanced during the activation process. The EMI shielding effectiveness (SE) of raw N330 carbon blacks filled with PVA was about 1 dB and those of the activated carbon blacks increased to the values between 6 and 9 dB. The EMI SE of raw N330 carbon blacks filled with PVDF was about 7 dB and the EMI SE increased to the range from 11 to 15 dB by the activation.