• Title/Summary/Keyword: Methyl

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Synthesis of N-Alkylated 4-Fluoro-5-phenylpyrrole-2-carboxylate via Isolable Pyrroline Ionic Intermediates

  • Kim, Sung-Kwan;Jun, Chang-Soo;Kwak, Kyung-Chell;Park, Kwang-Yong;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • v.28 no.12
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    • pp.2324-2328
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    • 2007
  • Organic fluorine chemistry produces many useful products. This paper elucidates the reaction of ethyl-4,4- difluoro-2-iodo-5-oxo-5-phenylpentanoate (2) with primary amines in a one-pot scheme. The reaction produced a series of β-fluoropyrrole derivatives at ambient temperatures. In this reaction, the less bulky the primary amine the higher was the resultant yield. When (2) and aqueous methylamine (40%) were allowed to react below 0 oC, 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2-hydroxy-2-phenylpyrrolidine, an intermediate molecule for 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2-carboxylate (5), was isolated first. Then, (5) reacted with hydroperchloric acid and acetic anhydride to form 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2- phenylpyrrolinium perchlorate (6), which was converted to 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2- carboxylate gradually in the presence of a base. Our experiments demonstrate that the formation of 2-ethyl-4- flouro-1-methyl-5-phenylpyrrole-2-carboxylate occurs via both one-pot schemes and stepwise pathways, depending on the reaction conditions. The isolation and characterization of the isolated intermediate (6) suggest an anionic pathway for this reaction.

Joint Toxic Action of Insecticide Mixtures to the Cupermethrin-and Pirimicarb-Selected Strains of Green Peach Aphid(Myzus pericae Sulzer) (Cypermethrin과 Pirimicarb 저항성계통 복숭아혹잔딧물에 대한 살충제문의 연합독작용)

  • 안용준;김길하;최승윤
    • Korean journal of applied entomology
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    • v.28 no.1
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    • pp.32-36
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    • 1989
  • The joint toxic action of mixtures of cypermethrin or pirimicarb with one of other insecticides (acephate, cypermethrin, demeton-S-methyl and pirimicarb) on the cypermethrin or picimicarb-selected green peach aphid (Myzus persicae Sulzer)was investigated. The responses depended on the choice and ratios of insecticide combination. In the cypermethrin-selected strain bioas-say, mixtures of test insecticides showed no synergistic effect. On the other hand, the maxi-mum synergistic effects for the pirimicarb-selected strain were obtained at the 8 : 2 ratio of pirimicarb and demeton-S-methyl exhibited antagonistic effect.

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Zinc Porphyrin-Cored Dendrimers; Axial Coordination of Pyridine and Photoinduced Electron Transfer to Methyl Viologen

  • Park, Ji-Eun;Choi, Dae-Ock;Shin, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.32 no.12
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    • pp.4247-4252
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    • 2011
  • The porphyrin-incorporated arylether dendrimers ZnP-D1 and ZnP-D4 were investigated to discover the influence of dendritic environments for the axial ligation of pyridine and photoinduced electron transfer by methyl viologen. Absorption and fluorescence spectra of ZnP, ZnP-D1, and ZnP-D4 were measured in dichloromethane with the addition of pyridine or methyl viologen dichloride. Axial ligation of pyridine was confirmed by red-shifted absorption spectrum. The complex formation constants $K_f$ (Table 1) for axial coordination of pyridine on ZnP, ZnP-D1, and ZnP-D4 were estimated to be $4.4{\times}10^3\;M^{-1}$, $3.3{\times}10^3\;M^{-1}$, and $1.7{\times}10^3\;M^{-1}$, respectively. The photoinduced electron transfer to methyl viologen dichloride was confirmed by fluorescence quenching. Stern-Volmer constants Ksv for ZnP, ZnP-D1, and ZnP-D4 were calculated to be $2.6{\times}10^3$, $2.5{\times}10^3$, and $2.1{\times}10^3$, respectively. ZnP-D4 surrounded by 4 aryl ether dendrons shows the smallest $K_f$ and Ksv values, with comparison to ZnP and ZnP-D1.

Isolation and structure elucidation of antifungal compounds from the antarctic lichens, Stereocaulon alpinum and Sphaerophorus globosus

  • Kim, Young-Shin;Lim, Chi-Hwan
    • Korean Journal of Agricultural Science
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    • v.47 no.1
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    • pp.183-191
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    • 2020
  • Lichens are composite organisms consisting of a symbiotic association of a fungus with a photosynthetic partner (the photobiont or phycobiont), usually either a green alga or cyanobacterium. According to more recent studies, the biological activities of lichens and lichen substances include an antibiotic activity, antitumor and antimutagenic activity against human immunodeficiency virus (HIV), allergenic activity, plant growth inhibitory activity, and enzyme inhibitory activity. This study screened lichen extracts with a potent in vitro antifungal activity against plant diseases caused by phytopathogenic fungi. The compounds were isolated from Stereocaulon alpinum and Sphaerophorus globosus, and their chemical structures were identified as methyl hematommate, methyl β-orsellinate, 5-hydroxyferulic acid, sphaerophorin, and 2-heptyl-4,6-dimethoxybenzoic acid by electron ionization mass spectrometry (EI-MS) and nuclear magnetic resonance (NMR) spectral analyses. In vitro disease control against Alternaria mali, Cochliobolus miyabeanus, Colletotrium gloeosporioides, and Verticillum dahliae was evaluated. And among the five compounds, only methyl hematommate was effective against A. mali, C. miyabeanus, and C. gloeosporioides. The compounds were isolated from these lichens, which have a similar biosynthetic pathway, respectively. This is the first report of these compounds being isolated from these lichens.

Absorption of Carbon Dioxide into Polar Solvents of 2-Amino-2-Methyl-1-Propanol (2-Amino-2-Methyl-1-Propanol이 용해한 극성 용매에서 이산화탄소의 흡수)

  • Son, Young-Sik;Heo, Nam-Hwan;Lee, Sung-Su;Park, Sang-Wook
    • Korean Chemical Engineering Research
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    • v.47 no.3
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    • pp.380-385
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    • 2009
  • The absorption rate of carbon dioxide with 2-amino-2-methyl-1-propanol(AMP) was measured in such non-aqueous solvents as methanol, ethanol, n-propanol, n-butanol, ethylene glycol, propylene glycol, and propylene carbonate, and in water at 298 K and 101.3 kPa using a semi-batch stirred tank with a plane gas-liquid interface. The overall reaction rate constant, obtained under the condition of fast reaction regime, from the measured rate of absorption was used to get the elementary reaction rate constants in complicated reactions represented by reaction mechanism of carbamate formation and the order of overall reaction of $CO_2$ with amine. The correlation between the elementary reaction rate constant and the solubility parameter of the solvent was also presented.

The Prediction of Vapor-Liquid Equilibrium Data for Ethanol/3-methyl-1-butanol System at Constant Temperature (정온하에서 Ethanol/3-methyl-1-butanol계의 기-액평형치 추산)

  • Lee, Joon-Man;Park, Young-Hae
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.14 no.4
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    • pp.2055-2061
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    • 2013
  • Recently, an understanding of new sources of liquid hydrocarbons such as bio-ethanol is economically very important. Successful design of distillation columns in a separation process depend on the availability of accurate vapor-liquid equilibrium data. For the binary system of Ethanol/3-methyl-l-butanol mixture, isothermal Vapor-liquid equilibrium data were measured at temperature of 50, 55, 60, 65, 70, 75 and $80^{\circ}C$. An empirical relation to predict Vapor-liquid equilibrium data was obtained from the above measured data. The predicted values are compared with the measured ones to be in a good agreement within accuracy of ${\pm}0.0005$, ${\pm}0.0022$.

Effects of Muscle Extracts of Fish and Shell-fish on the Oxidation of Methyl Linoleate (어패육추출물(魚貝肉抽出物)이 지질산화(脂質酸化)에 미치는 영향(影響))

  • Lee, Kang-Ho;Jeong, In-Hak;Lee, Jong-Ho
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.13 no.4
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    • pp.444-450
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    • 1984
  • Effects of muscle extracts of five species of fish and shell-fish, mackerel, jack mackerel, yellow corvenia, shrimp and baby-neck clam, on lipid oxidation were investigated using a model system consisting of methyl linoleate absorbed in micro crystalline cellulose and extracts of fishes. Ethanol extracts of both mackerel and jack mackerel apparently showed inhibitory effect on the oxidation of methyl linoleate, while the extract of yellow corvenia, and baby-neck clam showed a slight catalyzed effect on contrary. The ethanol extract of shrimp, however, revealed no effect on the oxidation of methyl linoleate. When the ethanol extracts were dialyzed, the outer fractions of dark fleshed fish had a strong inhibitory effect on the oxidation of methyl linoleate, while the inner fractions did not. The outer fraction of yellow corvenia showed catalyzed effect, but the inner fraction inhibited the oxidation slightly. The outer fraction of shrimp had a strong inhibitory action, but the inner fraction showed no effect. The methanol-water fraction of chloroform-methanol extract of shrimp showed a quite strong inhibitory effect on the oxidation, whereas that of four other samples did the same levels of effect as ethanol extracts.

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A Study on the Synthesis and Refining of Isothiazoline Derivatives (Isothiazoline 유도체의 합성 및 정제에 관한 연구)

  • Sung, Ki-Chun;Kim, Ki-Jun
    • Journal of the Korean Applied Science and Technology
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    • v.14 no.2
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    • pp.93-102
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    • 1997
  • Isothiazoline derivatives is widely used to food, medical drug and industrial goods, cosmetics etcs, and it makes to restrain and to sterilize a breeding of microbe as a preservative and a sterilizing agent. It differs with the raw material of paraoxybenzoic acid derivatives or imidazolydinyl urea to be in use at present, on the efficacy and effect, and has various characteristics. This synthesis makes 3,3'-dithiodipropionic chloride to add a thionyl chloride in 3,3'-dithiodipropionic acid, and 3,3'-dithiodipropionic methyl amide makes to synthesize in a reflux reaction the mono methyl amine to 3,3'-dithiodipropionic chloride. And last synthesis becomes to make chlorination-cyclization molecule doing a reflux reaction in the temperature of $90{\sim}100^{\circ}C$ to mix excessively thionyl chloride and ethylene dichloride to 3,3'-dithiodipropionic methyl amide. The last synthesis material has got in the mixture of 5-chloro-2-methyl-4-isothiazoline-3-one and 2-methyl-4-isothiazoline-3-one, and it is so-called isothiazoline derivatives. The purification of isothiazoline derivatives makes to fuse in ethyl acetate, and makes to decolorize and to deodorize in recrystallization. This experiment has been in synthesis and purification of isothiazoline derivatives, and has tried to measure on the antisepsis and sterilization function of microbe according to pH or content change.

The antimicrobial compound of Rhus verniciflua barks against fish pathogenic gram-negative bacteria, Edwardsiella tarda and Vibrio anguillarum (어류병원성 그람음성세균 Edwardsiella tarda와 Vibrio anguillarum에 대한 칠피의 항균활성물질)

  • Kang, So-Young
    • Journal of fish pathology
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    • v.18 no.3
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    • pp.227-237
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    • 2005
  • To obtain antimicrobial compounds against fish pathogenic bacteria from natural products, 80% methanolic extracts from 14 species of medicinal plant were screened for antimicrobial activity against fish pathogenic bacteria, Edwardsiella tarda and Vibrio anguillarum. Among them, Glycyrrhiza glabra, Rhus vemiciflua and Sanguisorba officinalis were effective for growth inhibition of Gram-negative bacteria, both E. tarda YSF and V. anguillarum YSR. Through the activity-guided isolation for R. verniciflua extract that exhibited the highest antimicrobial activity among three extracts, one antimicrobial compound (1) was isolated and identified as methyl-3,4,5-trihydroxybenzoate, or methyl gallate. This compound significantly inhibited the growth of tested strains of both E. tarda and V. anguillarum exhibiting MIC of 1 mg/ml for each strain.

Studies on the Chemical Components and Antioxidative Effect of Solanum lyratum Thunb (배풍등의 화학성분 및 항산화 효과에 관한 연구)

  • Shim, Kyung-Hee;Young, Han-Suk;Lee, Tae-Woong;Choi, Jae-Sue
    • Korean Journal of Pharmacognosy
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    • v.26 no.2
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    • pp.130-138
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    • 1995
  • Phytochemical study on the aerial parts of Solanum lyratum (Solanaceae) was carried out. On the basis of phytochemical and spectroscopic evidences, compound I was identified as mixtures of hexadecanoic acid methyl ester, 2,6,10,15-tetramethyl heptadecane, tricosane, tetracosane, pentacosane, docosanoic acid methyl ester, docosane, tricosanoic acid methyl ester, 8-hexyl pentadecane, tetracosanoic acid methyl ester, pentatriacontane, hexatriacontane, eicosane, hexacosane, hentriacontane and stigmasta-5,23-dien $3-{\beta}-ol$, and compound II, III, IV and V were identified as hexacosanoic acid methyl ester, ${\beta}-sitosterol-{\beta}-{_D}-glucoside$, $3-O-{\alpha}-{_L}-rhamnopyranosyl-(1->2)-{\beta}-{_D}-glucuronopyranosyl$ diosgenin and $3-O-{\alpha}-{_L}-rhamnopyranosyl-(1->6)-{\beta}-{_D}-glucopyranosyl$ quercetin (rutin), respectively. Rutin was identified as one of the active principles having antioxidative effect from S. lyratum.

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