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Molecular design of macrocyclic cyclophanes having molecular recognition like cyclodextrins

Research Project

Project/Area Number 05453130
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

TASHIRO Masashi  KYUSHU UNIVERSITY,INSTITUTE OF ADVANCED MATERIAL STUDY,PROFESSOR, 機能物質科学研究所, 教授 (40038576)

Co-Investigator(Kenkyū-buntansha) SAWADA Tsuyoshi  KYUSHU UNIVERSITY,INSTITUTE OF ADVANCED MATERIAL STUDY,RESEARCH ASSOCIATE, 機能物質科学研究所, 助手 (90240902)
MATAKA Shuntaro  KYUSHU UNIVERSITY,INSTITUTE OF ADVANCED MATERIAL STUDY,ASSOCIATE PROFESSOR, 機能物質科学研究所, 助教授 (10038599)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1994: ¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1993: ¥5,000,000 (Direct Cost: ¥5,000,000)
KeywordsCyclophane / Macrocyclic Compound / Host-Guest Property / Sulfur Method / Conplexation Reaction / Thiophene / Diels-Alder Reaction / Oxidative / 錯形成反応 / 脱メチル化 / 渡環反応 / テトラヒドロピレン体 / [2.2]メタシクロファン / ジアゾカップリング反応 / スルースペース効果 / フリーデルクラフト反応 / 多環シクロファン化合物
Research Abstract

Macrocyclic cyclophanes are able to change the size of their cavities, depending upon the length of the carbon bridges and numbers of aromatic rings.
Therefore, preparations of various types of host molecules, which recognize and interact with a given guest molecule, have been intensively investigated.
In 1995 fiscal year, the proposed study by the authors have been forcused on preparations, chemical modifications, and their molecular recognition behaviors of aromatic macrocyclic compounds. Also, preparations and reactions of [2.2] metacyclophane derivatives have been carried out.
The follwoings are the summaries of the studies in 1994.4-1995.3
1) Oxidative cycloaddition reaction of thiopenes with m-chloroperbenzoic acid was developed. This reaction was found useful in the preparation of various types of macrocyclic cyclophanes. Macrocyclic polyethers prepared by the above method were found to include metal ions with a high selectivity.
2) Calix [4] arene having two crbohydrate subunits was prepared for the first time.
3) [2.2] Metacyclophane having a 18-crown-6 was found to form a stable diazonium salt. A series of [2.2] naphtophanes were prepared and their conformational behaviors were clarified.
4) A convenient one step preparation of macrocyclic metacyclophanes having 6 or 8 diphenylmethane-substructures was newly developed.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] Masashi Tashiro: "Bromination of〔2.n〕Metacyclophan-1-enes and Isolation of Two Isomers of 1-Bromo〔2.n〕metacyclophan-1-enes" Chemische Berichte. 126. 447-451 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized〔2.n〕Metacyclopan-1-enes and Isolation of Two Isomers of 1-Bromo〔2.n〕metacyclophan-1-enes" Journal of Chemical Research(S). 5. 198-199 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Synthesis and Desulfurization of 2,11-Dithia〔3〕metacyclo-and 2,11-Dithia〔3〕paracyclo〔3〕(4.9)perenophanes" Chemische Berichte. 126. 2505-2511 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part 27.Reaction of 8-Methoxy-16-methy1〔2.2〕metacyclophanes with Boron Tribomide" Journal of Chemical Research(S). 7. 272-273 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Evaluation of Through-Space Interaction in〔2.2〕Metacyclophanes by Diazo Coupling Reaction" Journal of Chemical Society,Perkin Transaction 1. 14. 2211-2215 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part 28.Preparation ofand Addition of Bromoine to anti-7,15-Di-tert-buty1-10,18-dimehoxy〔4.2〕-metacyclophan-11-ene and Dehydrobromination fo the Bromine Adduct" Journal of Chemical Research(S). 10. 394-395 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "The Stability Constants for the 18-Crown-6 Complexes with〔2.2〕Metacyclophanediazonius Salts" Bulletin of the Chemical Society of Japan. 67. 277-279 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-Sized Cyclophanes.Part 31.Synthesis and Electrophilic Substitution of 8-Subsitituted〔2〕Metacyclo〔2〕(1.3)pyrenophanes" Jounal of Chemical Society,Perkin Transaction 1. 21. 3127-3137 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-Sized Cyclophanes.Part 32.Synthesis and Conformational Studies of (1.4)Naphthaleno〔2.2〕metacyclophnes" Journal of Chemical Research(S). 6. 210-211 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "SO-Photoextusion of 7-Thiabicyclo〔2.2.1〕hept-2-ene 7-Oxides" Bulletin of the Chemical Society of Japan. 67. 1866-1893 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part34.Demethylation of 8-Methoxy-〔2.2〕metacyclophanes with Trimethylsilyll Iodide" Journal of Chemical Research(S). 7. 210-211 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Synthesis of Benzothazoly1〔2.2〕metacyclophanes and Their Structural and Spectral and Spectral Properties" Chemistry Letters. 8. 1529-1532 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Novel Crown Ethers By Oxidative Cycloaddition of Thiopheno Crown Ethers" Jorrnal of chemical socity,perkin transaction 1. 15. 2323-2329 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Bromination of [2.n] Metacyclophane-1-enes and Isolation of Two Isomers of 1-Bromo [2.n] metacyclophane-1-enes" Chem.Ber.Vol.126. 447-451 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part 26.Electrophilic Substitiution of [2.2.2] (1,2,3) Cyclophanes" J.Chem.Research (S). No.5. 198-199 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Synthesis and Desulfurization of 2,11-Dithia [3] -metacyclo- and 2,11-Dithia [3] paracyclo [3] (4,9) -pyrenophanes" Chem.Ber.Vol.126. 2505-2511 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part.27.Reaction of 8-Methoxy 16-metyl [2.2] metacyclopahnes with Boron Tribron Tribromide" J.Chem.Research (S). No.7. 272-273 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "sEvaluation of Through-Space Interaction in [2.2] Metacyclophanes by Diazo Coupling Reaction" J.Chem.Soc., Perkin Tran. No.14. 2211-2215 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part.28.Preparation of and Addition of Bromoine to anti-7,15-Di-tert-butyl-10,18-dimethoxy [4.2] metacyclophan-11-ene and Dehydrobromination of the Bromine Adduct" J.Chem.Research (S). No.10. 394-395 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "The Stability Constants for the 18-Crown-6 Complexes with [2.2] Metacyclopahnediazonium Salts" Bull.Chem.Soc.Jpn.Vol.67. 277-279 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-Sized Cyclophanes.Part 31.Synthesis and Electrophilic Substitution of 8-Substituted [2] Metacyclo [2] (1,3) pyrenophanes" J.Chem.Soc.Perkin Trans. 1, No.21. 3127-3137 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part 32.Synthesis and Conformational Studies of (1,4) Naphthaleno [2.2] metacyclophanes" J.Chem.Research (S). No.6. 210-211 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "SO-Photoextrusion of 7-Thiabicyclo [2.2.1] hept-2-ene 7-Oxides" Bull.Chem.Soc.Jpn.Vol.67. 1886-1893 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Medium-sized Cyclophanes.Part 34.Demethylation of 8-Methoxy [2.2] metacyclophanes with Trimethylsilyll Iodide" J.Chem.Research (S). No.7. 246-247 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Synthesis of Benzothiazolyl [2.2] metacyclophanes and Their Structural and Spectral Properties" Chem.Lett.No.8. 1529-1532 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi Tashiro: "Novel Crown Ethers by Oxidative Cycloaddition of Thiopheno Crown Ethers" J.Chem.Soc.Perkin Trans.1, No.15. 2323-2329 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masashi,Tashiro: "The Stability Constants for the 18-Crown-6 Complexes with[2.2]Metacyclophane-diazonium Salts" Bulletin of the Chemical Society of Japan. 67. 277-279 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masashi,Tashiro: "SO-Photoextrusion of 7-Thiabicyclo[2.2.1]hept-2-ene 7-Oxides" Bulletin of the Chemical Society of Japan. 67. 1866-1893 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masashi,Tashiro: "Novel Crown Ethers By Oxidative Cycloaddition of Thiopheno Crown Ethers" Journal of Chemical Society,Perkin Transaction 1. 16. 2323-2329 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masashi,Tashiro: "Synthesis of Benzothazoly[2.2]metacyclophanes and Their Structural and Spectral and Spectral Properties" Chemistry Letters. 8. 1529-1532 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M,Tashiro: "Medium-sized Cyclophanes.Part2 6^1Electrophilic Substituion of [2.2.2](1,2,3)Cyclophanes" Journal of Chemical Research(S). 7. 272-273 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M,Tashiro: "Medium-sized Cyclophanes.Part27,^1Reaction of 8-Methoxy-16-Methul[2.2]metacyclophanes with Boron Tribromide" Journal of Chemical Research(S). 5. 198-199 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M,Tashiro: "Evaluation of Through-Space Interaction in [2.2]-Metacyclophanes by Diazo Coupling Resction" Journal of the Chemical Society Perkin Transaction 1. 3. 2211-2215 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M,Tashiro: "Synthesis and Desulfurization of 2,11-Dithia[3]metacyclo-and 2,11-Dithia[3]paracyclo[3](4,9)Pyrenophanes" Chemische Brichte. 126. 2505-2511 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M,Tashiro: "特異な場をもつシクロファン系化合物の反応性と機能性" 九州大学機能物質科学研究所. 7. 71-102 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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