• Title/Summary/Keyword: Grignard Reaction

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Synthesis and Characterization of Novel Fused Aromatic Materials

  • Park, Jong-Won;Zhao, Qing-Hua;Kim, Tae-Hoon;Yi, Mi-Hye;Kim, Yun-Hi;Kwon, Soon-Ki
    • 한국정보디스플레이학회:학술대회논문집
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    • 2007.08a
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    • pp.174-178
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    • 2007
  • A series of new oligomers were synthesized by Grignard reaction, the Suzuki coupling reaction, etc. The oligomers showed excellent TFT performance with mobilities higher than $0.5\;cm^2V^{-1}S^{-1}$ and on/off ratios higher than 5 $x10^5$. Their electronic and optical properties were investigated using many analysis methods, such as X-ray diffraction (XRD), UV-vis and photoluminescence spectroscopies.

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Synthesis of the Anthelmintic Diaryl Butanes against Clonorchis sinensis (간흡충에 대하여 구충작용을 갖는 Diarylbutane류의 합성)

  • 주정숙;류성호;우병태;백병걸;이재구;안병준
    • YAKHAK HOEJI
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    • v.29 no.4
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    • pp.183-187
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    • 1985
  • During investigation of the anthelmintic substances against Clonorchis sinensis which are based on the structure of meso-dihydroguairaretic acid, some non-mesoic diaryl butanes were synthesized by Grignard reaction and their anthelmintic activities were determined. In this reaction, an aryl butanone was reacted with benzylmagnesium chloride to produce the corresponding diaryl hydroxybutane which was converted to the corresponding diaryl butane by zinc and hydrogen chloride. The substituents in benzene ring of the diaryl butanes were changed by methylation or demethylation. Among the synthesized substances, 4-phenyl-1-(3, 4-dihydroxyphenyl)-2, 3-dimethylbutane(VII), 4-phenyl-1-(3-hydroxy-4-methoxyphenyl)-2, 3-dimethylbutane(IX) and 4-phenyl-1-(4-hydroxy-3-methoxyphenyl)-2, 3-dimethylbutane(VI) showed strong wormicidal effects against Clonorchis si-nensis in that order. Phenolic hydroxyl group seemed to play a certain role for the wormicidal activity of the diaryl butanes.

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Improvement of Radiosynthesis Yield of [11C]acetate ([11C]아세트산의 방사화학적 수율 증가를 위한 연구)

  • Park, Jun Young;Son, Jeongmin
    • The Korean Journal of Nuclear Medicine Technology
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    • v.22 no.2
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    • pp.74-78
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    • 2018
  • Purpose $[^{11}C]$acetate has been proved useful in detecting the myocardial oxygen metabolism and various malignancies including prostate cancer, hepatocellular carcinoma, renal cell carcinoma and brain tumors. The purpose of study was to improve the radiosynthesis yield of $[^{11}C]$acetate on a automated radiosynthesis module. Materials and Methods $[^{11}C]$acetate was prepared by carboxylation of grignard reagent, methylmagnesium chloride, with $[^{11}C]$$CO_2$ gas, followed by hydrolysis with 1 mM acetic acid and purification using solid phase extraction cartridges. The effect of the reaction temperature ($0^{\circ}C$, $10^{\circ}C$, $-55^{\circ}C$) and cyclotron beam time (10 min, 15 min, 20 min, 25 min) on the radiosynthesis yield were investigated in the $[^{11}C]$acetate labeling reaction. Results The maximum radiosynthesis yield was obtained at $-10^{\circ}C$ of reaction temperature. The radioactivities of $[^{11}C]$acetate acquired at $-10^{\circ}C$ reaction temperature was 2.4 times higher than those of $[^{11}C]$acetate acquired at $-55^{\circ}C$. Radiosynthesis yield of $[^{11}C]$acetate increased with increasing cyclotron beam time. Conclusion This study shows that radiosynthesis yield of $[^{11}C]$acetate highly dependent on reaction temperature. The best radiosynthesis yield was obtained in reaction of grignard reagent with $[^{11}C]$$CO_2$ at $-10^{\circ}C$. This radiolabeling conditions will be ideal for routine clinical application.

Adhesive Property of Novel Polyimides Containing Fluorine and Phosphine Oxide (Phosphine oxide와 불소를 함유하는 폴리이미드의 접착성 연구)

  • Jeong, K.U.;Myung, B.Y.;Cho, Y.J.;Choi, I.J.;Yoon, T.H.
    • Journal of Adhesion and Interface
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    • v.1 no.1
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    • pp.38-46
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    • 2000
  • A novel diamine monomer, containing fluorine and phosphine oxide, bis(3-aminophenyl) 3,5-bis(trifluoromethyl) phenyl phosphine oxide (mDA6FPPO), was prepared via Grignard reaction, and utilized to prepare polyimides with dianhydrides such as PMDA, 6FDA, BTDA or ODPA, by the conventional two-step route; preparation of poly(amic acid), followed by solution imidization. The polyimides were characterized by FT-lR, NMR, DSC and DMA, with intrinsic viscosity, and adhesive properties were also evaluated. A phosphine oxide containing monomer, bis(3-aminophenyl) phenyl phosphine oxide (mDAPPO) a nd a commercial 3,3'-diamino diphenyl sulfone (mDDS) were also used for comparison. The polyimides with mDA6FPPO exhibited high $T_g$, excellent solubility, and good adhesive properties.

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AN IMPROVED ANALYSIS FOR DETERMINATION OF MONOVINYL AND DIVINYL PROTOPORPHYRIN IX

  • Kim, Jin-Seog;Rebeiz, Constantin A.
    • Journal of Photoscience
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    • v.2 no.2
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    • pp.103-106
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    • 1995
  • For studying chlorophyll biosynthetic heterogeneity of plants, it is necessary to establish a technique for microassay of a putative monovinyl and divinyl protoporphyrin IX. Precise determination of the amounts of monovinyl and divinyl protoporphyrin IX is difficult with optical electronic spectroscopy even at 77$\circ$C. Such a problem could be solved by conversion of protoporphyrin IX to protoporphyrin IX dimethylester with diazomethane and subsequent Mg insertion into protoporphyrin IX dimethylester by reaction with a Grignard solution. The proportion of monovinyl and divinyl Mg-protoporphyrin IX dimethylester formed was measured instead of direct measuring that of protoporphyrin IX by low-temperature spectrofluorometry. The relative proportions of monovinyl and divinyl of protoporphyrin IX, Mg-protoporphyrin IX, and Mgprotoporphyrin IX dimethylester have not changed during the chemical conversion steps. This analysis system could be useful for the study of the monovinyl and divinyl chlorophyll biosynthetic routes in plants.

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Synthesis and Characterization of Novel Aromatic Polyimides from Bis (3-aminophenyl) 3,5-bis (trifluorormethyl) phenyl Phosphine Oxide

  • Jeong, Kwang-Un;Kim, Jang-Joo;Yoon, Tae-Ho
    • Macromolecular Research
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    • v.8 no.5
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    • pp.215-223
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    • 2000
  • A novel diamine monomer, containing fluorine and phosphine oxide, bis(3-aminophenyl) 3,5-bis(trifluoromethyl)phenyl phosphine oxide (mDA6FPPO), was prepared via Grignard reaction, and utilized to prepare polyimides with dianhydrides such as PMDA, 6FDA, BTDA or ODPA, by the conventional two-step route; preparation of poly(amic acid), followed by solution imidization. The polyimides were characterized by FT-IR, NMR, and DSC with intrinsic viscosity and refractive index also being evaluated. A phosphine oxide containing monomer, bis(3-aminophenyl)phenyl phosphine oxide (mDAPPO) and a commercial 3,3-diaminodiphenyl sulfone (mDDS) were also used for comparison. The polyimides derived from mDA6FPPO exhibited high T$\sub$g/, excellent solubility and low birefringence.

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Synthesis and in vitro Cytotoxicity Monoterpenoid as New Antitumor Agents (Monoterpenoid계의 새로운 항암제 합성 및 In vitro 세포독성 평가)

  • 이민정;김대근;백형근;이강노;정규혁
    • Biomolecules & Therapeutics
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    • v.9 no.3
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    • pp.143-155
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    • 2001
  • Many attention has been focused on developing new chemotherapeutic agents for a treatment of cancer from natural products. From Carpesium divaricatum S. et Z. (Compositae), various monoterpenoid compounds were isolated and exhibited mild antitumor activity against human tumor cell lines. These facts prompted us to explore the structure-activity relationship of these compounds. The synthesis of monoterpenoid compound was accomplished by Fries rearrangement, Grignard reaction, elimination, allylic oxidation, esterification and epoxidation as key steps. The results of in vitro cytotoxicity (A549, SK-OV-3, SK-MEL-2, XF498, HCT15) of the synthesised compounds are as follows: First of all, epoxide moiety is prerequisite for cytotoxic activity in diester compound. Any kind of compounds with olefin or diol moiety instead of epoxide ring exhibited poor or mild cytotoxic activity respectively. Of o-acetoxy and isobutoxy epoxy esters, p-sub-stituted phenylacetate compounds exhibited high cytotoxic activities against SK-MEL-2 and HCT15.

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Synthesis and Evaluation of Biological Properties of Benzylide-neacetophenone Derivatives

  • Oh, Sei-Kwan;Jang, So-Yong;Kim, Dong-Hyun;Han, Inn-Oc;Jung, Jae-Chul
    • Archives of Pharmacal Research
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    • v.29 no.6
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    • pp.469-475
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    • 2006
  • A series of yakuchinone B 1f and its analogs 1a-e was synthesized and evaluated for free radical scavenging, suppression of LPS-induced NO generation, cytotoxicity and anti-excitotoxicity in vitro. Compound 1c exhibited potent anti-excitotoxicity, while all compounds 1a-f showed considerable effects of free radical scavenging, suppression of LPS-induced NO generation, and cytotoxicity in microglia.

A Total Synthesis of Nuciferal and Nuciferol

  • Lee, Woo-Young;Lee, Youn-Young;Lim, Kwang-Su;Goo, Yang-Mo;Park, Oee-Sook
    • Bulletin of the Korean Chemical Society
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    • v.9 no.6
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    • pp.379-381
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    • 1988
  • Racemic nuciferal(1) and nuciferol(2), the terpenic natural perfumeries, have been synthesized by a simple procedure. The benzylic halide 6; 1-(1-chloroethyl)-4-methylbenzene, was prepared by converting p-tolualdehyde(4) into 1-(p-tolyl)-1-ethanol(5), followed by convertion of 5 into corresponding chloride. The Grignard reagent of 6 was reacted with the bromoacetal 7, 2-(2-bromoethyl)-1,3-dioxolane, to give a crosscoupling product 8, which was hydrolysed to 4-(p-tolyl)-pentanal (9). The Wittig reaction of isopropylide 10 with 9 yielded arcurcumen(11). The stereospecific allylic oxidation of the gem-dimethyl olefin 11 with selenium dioxide afforded a trans-aldehyde, (${\pm}$)-1, which was reduced to corresponding alcohol, (${\pm}$)-2.

Formal Synthesis of Isocomene

  • Hyo Won Lee;Jae Hyun Lee;Ihl-Young Choi Lee
    • Bulletin of the Korean Chemical Society
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    • v.12 no.4
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    • pp.392-397
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    • 1991
  • A stereocontrolled synthesis of (${\pm}$)-isocomene (1) via selective monoketalization of tricyclo[6.3.0.$0^{1.5}$]undeca-4,7-dione(13) was reported. Grignard reaction of bicyclic enone 10, which was prepared from 2-methyl-1,3-cyclopentadione, gave the 1,4-addition product 11. The subsequent aldol condensation product 12 was converted to mesyl derivative 13. Transformation from 13 to the desired product 19 was achieved by a series of reactions, i.e., the selective monoketalization at C-4 carbonyl group, the elimination of a mesyl group, Birch alkylation, methylation at C-6, the reduction of carbonyl group, the dehydration of alcohol 18, and hydrolysis of the ketal group.