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Development of highly active organocatalyst by use of fluorogenic probes for chemical transformations

Research Project

Project/Area Number 23685035
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Environmental chemistry
Research InstitutionShizuoka University

Principal Investigator

MASE NOBUYUKI  静岡大学, 工学研究科, 教授 (40313936)

Project Period (FY) 2011-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥25,220,000 (Direct Cost: ¥19,400,000、Indirect Cost: ¥5,820,000)
Fiscal Year 2014: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2013: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2012: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2011: ¥8,060,000 (Direct Cost: ¥6,200,000、Indirect Cost: ¥1,860,000)
Keywords化学結合形成検出用センサー / 蛍光センサー / OFF-ONセンサー / 触媒探索 / 環境調和型触媒 / 有機分子触媒 / エナミン触媒 / イミニウム触媒 / 化学結合検出用センサー / アルドール反応 / マンニッヒ反応
Outline of Final Research Achievements

Fluorogenic substrates or probes for chemical transformations, molecules that show no or very low fluorescence but show high fluorescence upon chemical transformations, are useful for monitoring the progress of chemical transformations, especially at the initial stages of the reaction. Assays using fluorogenic substrates accelerate the identification of superior catalysts and reaction conditions in high-throughput formats as well as characterization of catalysis on a small scale. Here, we studied the development of aldehyde, imine, and enals-type fluorogenic probes and their use in monitoring various organocatalytic chemical transformations, including C-C bond-forming reactions such as aldol, Mannich, and Diels-Alder reactions. The best combinations of amine catalyst and acid additive in both enamine and iminium catalysis were identified. In conclusion, we have developed fluorogenic compounds that can be used for rapid monitoring chemical reactions through increased fluorescence.

Report

(5 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (44 results)

All 2015 2014 2013 2012 2011 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 1 results,  Open Access: 1 results) Presentation (27 results) (of which Invited: 6 results) Book (7 results) Remarks (4 results)

  • [Journal Article] Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO2014

    • Author(s)
      Mase, N.; Ando, T.; Shibagaki, F.; Sugita, A.; Narumi, T.; Toda, M.; Watanabe, N.; Tanaka, F.
    • Journal Title

      Tetrahedron Letters

      Volume: 55 (11) Issue: 11 Pages: 1946-1948

    • DOI

      10.1016/j.tetlet.2014.02.007

    • NAID

      120005441930

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Characterization of Quantum Dot Nanoparticles Bound to the Plant Volatile Precursor of Hydroxy-apo-10 '-carotenal2014

    • Author(s)
      Tu, V. A.; Kaga, A.; Gericke, K. H.; Watanabe, N.; Narumi, T.; Toda, M.; Brueckner, B.; Baldermann, S.; Mase, N.
    • Journal Title

      Journal of Organic Chemistry

      Volume: 79 (15) Issue: 15 Pages: 6808-6815

    • DOI

      10.1021/jo500605c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence2013

    • Author(s)
      Mase, N.; Takabe, K.; Tanaka, F.
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 32 Pages: 4306-4308

    • DOI

      10.1016/j.tetlet.2013.06.010

    • NAID

      120005349329

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Micro and Nanobubble Based Strategy for Gas-Liquid-Solid Multiphase Reactions: Palladium-Catalysed Hydrogenation of Carbon-Carbon Unsaturated Bonds2013

    • Author(s)
      Mase, N.; Isomura, S.; Toda, M.; Watanabe, N.
    • Journal Title

      Synlett

      Volume: 24 Issue: 17 Pages: 2225-2228

    • DOI

      10.1055/s-0033-1339798

    • NAID

      120005479948

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Knoevenagel Condensations by Means of Carbamic Acid Ammonium Salts2013

    • Author(s)
      Mase, N.; Horibe, T.
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 8 Pages: 1854-1857

    • DOI

      10.1021/ol400462d

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Knoevenagel Condensations by Means of Carbamic Acid Ammonium Salts2013

    • Author(s)
      Nobuyuki Mase* and Takuya Horibe
    • Journal Title

      Organic Letters

      Volume: 15 (8) Pages: 1854-1857

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] Diels-Alder反応における蛍光スクリーニング法による有機分子触媒の探索2015

    • Author(s)
      増田 嗣也・鳴海 哲夫・渡辺 修治・間瀬 暢之
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Mannich反応における蛍光スクリーニング法による有機分子触媒の探索2015

    • Author(s)
      佐々木 愛子・鳴海 哲夫・渡辺 修治・間瀬 暢之
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 静岡から発信する環境調和型有機合成プロセス ~有機分子触媒からマイクロバブル・ナノバブルまで~2015

    • Author(s)
      間瀬 暢之
    • Organizer
      徳島大学 特別講演会
    • Place of Presentation
      徳島大学(徳島県、徳島市)
    • Year and Date
      2015-01-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Self-Assembling GNP-Supported Organocatalysts: Application for Asymmetric Synthesis2015

    • Author(s)
      Peter Lajos Soti, Tetsuo Narumi, Naoharu Watanabe, Nobuyuki Mase
    • Organizer
      2015 International Symposium toward the Future of Advanced Researches in Shizuoka University
    • Place of Presentation
      静岡大学(静岡県、浜松市)
    • Year and Date
      2015-01-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] Organic Synthetic Methodology Based on Process and Green Chemistry2014

    • Author(s)
      間瀬 暢之
    • Organizer
      Global Green Challenge
    • Place of Presentation
      クアラルンプール(マレーシア)
    • Year and Date
      2014-12-15
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 静岡発(初)の環境調和型有機合成プロセス ~有機分子触媒からマイクロバブル・ナノバブルまで~2014

    • Author(s)
      間瀬 暢之
    • Organizer
      名城大学 特別研究講演会
    • Place of Presentation
      名城大学(愛知県、名古屋市)
    • Year and Date
      2014-12-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of GNP-Supported Organocatalyst for Asymmetric Aldol Reaction2014

    • Author(s)
      Peter Lajos Soti, Tetsuo Narumi, Naoharu Watanabe, Nobuyuki Mase
    • Organizer
      Directions in Interdisciplinary Domain Research through Japan-Indonesia Partnership
    • Place of Presentation
      静岡市(静岡県)
    • Year and Date
      2014-12-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] Organic Synthetic Methodology Based on Process and Green Chemistry2014

    • Author(s)
      間瀬 暢之
    • Organizer
      Directions in Interdisciplinary Domain Research through Japan-Indonesia Partnership
    • Place of Presentation
      静岡市(静岡県)
    • Year and Date
      2014-12-01
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Synthesis and application of self-assembling GNP supported organocatalysts2014

    • Author(s)
      Peter Lajos Soti, Tetsuo Narumi, Naoharu Watanabe, Nobuyuki Mase
    • Organizer
      Advanced Molecular Transformations by Organocatalysts 2nd International Conference & 7th Symposium on Organocatalysis
    • Place of Presentation
      東京大学(東京都)
    • Year and Date
      2014-11-21
    • Related Report
      2014 Annual Research Report
  • [Presentation] 静岡発(初)の環境調和型合成プロセスの開発を夢見て ~有機分子触媒からマイクロバブル・ナノバブルまで~2014

    • Author(s)
      間瀬 暢之
    • Organizer
      有機合成化学協会東海支部 若手研究者のためのセミナー
    • Place of Presentation
      岐阜薬科大学(岐阜県、岐阜市)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 静岡発(初)の環境調和型合成プロセス~有機分子触媒からマイクロバブル・ナノバブルまで~2014

    • Author(s)
      間瀬 暢之
    • Organizer
      大阪大学産業科学研究所 講演会
    • Place of Presentation
      大阪大学産業科学研究所(大阪府)
    • Year and Date
      2014-07-11
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 炭素-炭素結合検出型蛍光モニタリング法による有機分子触媒系の特定2014

    • Author(s)
      間瀬 暢之, 佐々木愛子, 伊藤大史
    • Organizer
      「有機分子触媒による未来型分子変換」第4回 公開シンポジウム
    • Place of Presentation
      北海道大学(北海道)
    • Year and Date
      2014-06-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] 蛍光スクリーニング法を用いた4 級炭素構築アルドール反応における有機分子触媒の最適化2014

    • Author(s)
      伊藤大史・間瀬暢之
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Annual Research Report
  • [Presentation] 蛍光スクリーニング法による反応選択的有機分子触媒の特定2014

    • Author(s)
      佐々木愛子・間瀬暢之
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Annual Research Report
  • [Presentation] 蛍光手法による4級炭素構築用アルドラーゼ型有機分子触媒の探索2013

    • Author(s)
      伊藤大史・間瀬暢之
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [Presentation] 4級炭素構築アルドール反応における有機分子触媒探索を指向したリアルタイム蛍光モニタリング2013

    • Author(s)
      伊藤大史・間瀬暢之
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Annual Research Report
  • [Presentation] 蛍光モニタリング手法による反応選択的有機分子触媒系の特定2013

    • Author(s)
      佐々木愛子・間瀬暢之
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡
    • Related Report
      2013 Annual Research Report
  • [Presentation] 触媒探索に有用な改良型OFF-ON蛍光センサーの合成とその蛍光特性2012

    • Author(s)
      南祐輔・間瀬暢之
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学・神奈川
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] グリーンケミストリーに基づいた環境調和型物質合成プロセスの開発2011

    • Author(s)
      間瀬暢之
    • Organizer
      スクリプスバイオメディカルフォーラム
    • Place of Presentation
      新大阪ワシントンホテルプラザ・大阪(招待講演)
    • Year and Date
      2011-12-03
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis of OFF-ON Fluorogenic Compounds and Its Application for Environmentally-Friendly Catalyst Screening2011

    • Author(s)
      Yusuke Minami, Naoki Koyama, Fumiya Shibagaki, Nobuyuki Mase
    • Organizer
      the Second International Symposium on Process Chemistry (ISPC 2011)
    • Place of Presentation
      Kyoto International Conference Center・Kyoto
    • Year and Date
      2011-08-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] 4級炭素構築アルドール反応における蛍光モニタリング法を用いた効率的有機触媒探索

    • Author(s)
      伊藤大史・佐々木愛子・間瀬暢之
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 (滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 2-アミノピリジン型有機分子触媒を用いた基質認識型エノラート形成によるマイケル付加反応

    • Author(s)
      加藤貴大・間瀬暢之
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 (滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 炭素-炭素結合検出型蛍光モニタリング法を用いた最適有機分子触媒の同定

    • Author(s)
      伊藤大史・佐々木愛子・間瀬暢之
    • Organizer
      第43回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      名古屋工業大学 (愛知県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 炭素-炭素結合検出型蛍光モニタリング法を用いた効率的有機触媒探索

    • Author(s)
      伊藤大史・佐々木愛子・間瀬暢之
    • Organizer
      第5回 有機触媒シンポジウム (<兼> 第2回公開シンポジウム)
    • Place of Presentation
      学習院大学 (東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] α‐アミノピリジン有機分子触媒を用いた基質認識型エノラート形成によるマイケル付加反応

    • Author(s)
      加藤貴大・間瀬暢之
    • Organizer
      第5回 有機触媒シンポジウム (<兼> 第2回公開シンポジウム)
    • Place of Presentation
      学習院大学 (東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 環境調和型物質合成プロセスの開発: 有機分子触媒からマイクロナノバブルまで

    • Author(s)
      間瀬暢之
    • Organizer
      第385回 薬学研究科セミナー
    • Place of Presentation
      東北大学 (宮城県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 4級炭素含有アルドール反応における蛍光モニタリングを用いた効率的有機分子触媒探索

    • Author(s)
      伊藤大史・佐々木愛子・間瀬暢之
    • Organizer
      日本プロセス化学会2012サマーシンポジウム
    • Place of Presentation
      京都テルサ (京都府)
    • Related Report
      2012 Annual Research Report
  • [Book] Comprehensive Organic Synthesis (2nd Edition): The aldol reaction: organocatalysis approach2014

    • Author(s)
      Mase, N.; Hayashi, Y.
    • Total Pages
      67
    • Publisher
      Elsevier
    • Related Report
      2014 Annual Research Report
  • [Book] Comprehensive Organic Synthesis, 2nd Edition 2.07 The Aldol reaction: organocatalysis approach2014

    • Author(s)
      Mase, N.; Hayashi, Y.
    • Total Pages
      66
    • Publisher
      Elsevier
    • Related Report
      2013 Annual Research Report
  • [Book] Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, 3 Volume Set; VOLUME 3: REACTIONS AND APPLICATIONS PART II. Nucleophile Addition to C = X Bonds Aldol and Mannich-Type Reactions2013

    • Author(s)
      Nobuyuki Mase, Carlos F. Barbas, III
    • Total Pages
      42
    • Publisher
      Wiley-VCH
    • Related Report
      2013 Annual Research Report
  • [Book] Science of Synthesis Knowledge Updates 2013/3; 19.5.14.15 Synthesis from Nitriles with Retention of the Cyano Group2013

    • Author(s)
      Nobuyuki Mase
    • Total Pages
      147
    • Publisher
      Thieme
    • Related Report
      2013 Annual Research Report
  • [Book] Comprehensive Chirality; Volume 6: Synthetic Methods V; Organocatalysis; 6.4 C-C Bond Formation: Aldol Reaction with Proline Derivatives2012

    • Author(s)
      Nobuyuki Mase
    • Publisher
      Elsevier
    • Related Report
      2012 Annual Research Report
  • [Book] Science of Synthesis 2011: Volume 2011/6: Asymmetric Organocatalysis 1: Lewis Base and Acid Catalysts; 1.1.4 Enamine Catalysis of Michael Reactions2012

    • Author(s)
      Nobuyuki Mase
    • Publisher
      Thieme
    • Related Report
      2012 Annual Research Report
  • [Book] Science of Synthesis 2011: Volume 2011/5: Water in Organic Synthesis; 3.4 Conjugate Addition Reactions2012

    • Author(s)
      Nobuyuki Mase
    • Publisher
      Thieme
    • Related Report
      2012 Annual Research Report
  • [Remarks] 静岡大学 間瀬研究室ホームページ

    • URL

      http://www.ipc.shizuoka.ac.jp/~tnmase/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 静岡大学 間瀬研究室

    • URL

      http://www.ipc.shizuoka.ac.jp/~tnmase/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 静岡大学 間瀬研究室

    • URL

      http://www.ipc.shizuoka.ac.jp/~tnmase/

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.ipc.shizuoka.ac.jp/~tnmase/

    • Related Report
      2011 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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