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Selective Electrosynthesis of Biologically Active Organofluorine Compound Using a Fluorine Mediator

Research Project

Project/Area Number 09650949
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTOKYO INSTITUTE OF TECHNOLOGY

Principal Investigator

FUCHIGAMI Toshio  Tokyo Institute of Technology, Interdisciplinary Graduate School of Sciences and Engineering Professor, 大学院・総合理工学研究科, 教授 (10016701)

Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1998: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsStereoselective synthesis / Mediator / Biologically active compound / Anodic substitution / Anodic cycliation / Organofluorine compound / Oxathiolane / Chiral compound / 光学活性オキサチオラン / 光学活性スルフィド / 光学活性トリフルオロメチル化合物 / 含フッ素化合物 / 電解メトキシ化 / 電解合成 / 1,2不斎誘導
Research Abstract

Although anodic substitutions are quite useful in organic synthesis since they can be done in one step, such subsitutions are limited to organic nitrogen compounds. Recently, we found that fluoride ions markedly promoted anodic substitutions of chalcogeno compounds. On the other hand, development of efficient selective synthetic methods of organofluorine compounds has been increasingly important since they have unique biological activities. However, due to specific fluorine atoms, their synthesis is not always easy.
From these viewpoints, we have attempted selective electrosynthesis of biologically active organofluorine compounds using a fluorine mediator as follows.
1) Fluoride ion mediated anodic alpha-methoxylation of 2-methoxy-3,3,3-trifluoropropyl phenyl sulfide and its synthetic application.
2) Electrosynthesis of beta-trifluoromethylated O,S-acetal and alpha-(trifluoromethyl)acrylate derivatives from 2-ethoxycarbonyl-3,3,3-trifluoropropyl phenyl sulfide using a fluoride ion mediator.
3) Fluoride ion mediated anodic alpha-methoxylation of 2-hydroxy-3,3,3-trifluoropropyl phenyl sulfide and its application to the synthesis of optically active organofluorine compounds.
4) Electrosynthesis of optically active oxathiolanes having a CF_3 group using a fluoride ion mediator.
We have acieved above four projects and found that some of electrosynthsized products show maked biological activities.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] 古田 昇二: "Electrosynthesis of β-Trifluoromethylated O_1S-Acetals and α-(Tri-fluoromethyl)acrylates Lising a Fluoride Ion Mediator" Journal of Fluorine Chemistry. 87. 209-214 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 古田昇二: "Fluoride Ion Mediated Anodic α-Methoxylation of 2-Methoxy-3, 3, 3-trifluoropproyl phenyl Sulfide an Its Synthetic Application" Electrochimica Acta. 43. 3153-3157 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 淵上 寿雄: "環境にやさしい有機電解合成" フアルマシア. 34. 1118-1122 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 淵上寿雄: "Advances in Electron Transfer Chemistry・Vol・6" JAI Press, 90 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta and T.Fuchigami: "Electrosynthesis using a fluoride ion mediator. IV : Fluoride ion mediated anodic alpha-methoxylation of 2-methoxy-3,3,3-trifluoropropyl phenyl sulfide and its synthetic application" Electrochimica Acta. 43. 3153-3157 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta, Y.Saito, and T.Fuchigami: "Electrosynthesis of beta-trifluoromethylated O,S-acetal and alpha-(trifluoromethyl)acrylate derivatives from 2-ethoxycarbonyl-3,3,3-trifluoropropyl phenyl sulfide using a fluoride ion mediator" J.Fluorine Chem. 87. 209-214 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Fuchigami: "Enviromentary Friendly Electroorganic Synthesis" Pharmacia. 34. 1118-1122 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Fuchigami: "Electrochemistry Applied to the Synthesis of Fluorinated Organic Substances" Advances in Electron-Transfer Chemistry, Vol6"ed.P.S.Mariano. JAIPress, CT. 41-130 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 古田昇二: "Electrosynthesis of β-Trifluoromethylated O_1S-Acetals and α-(tri-fluoromethyl)acrylates Using a Fluoride Ion Mediate-" Journal of Fluorine Chemistry. 87. 209-214 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 古田昇二: "Fluoride Ion Mediated Anodic α-Methoxylation of 2-Medioxy-3,3,3-trifluoropropyl Phenyl Sulfide and Its Synthetic Application" Electrochimica Acta. 43・21/22. 3153-3157 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 渕上寿雄: "Advances in Electron Transfer Chemistry.Vol.6" JAI Press, 90 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] 渕上 寿雄: "Adrances in Electron Transfer Chemistry" JAI Press, (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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