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Synthesis and Application of Conjugated Polyene Molecules by a Direc pi-Expansion Reaction

Research Project

Project/Area Number 17H03051
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

Hirano Masafumi  東京農工大学, 工学(系)研究科(研究院), 教授 (70251585)

Project Period (FY) 2017-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Fiscal Year 2021: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2020: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2017: ¥8,190,000 (Direct Cost: ¥6,300,000、Indirect Cost: ¥1,890,000)
Keywords交差二量化 / 合成ビルディングブロック / 天然物の合成 / 有機半導体物質 / ジボリ化共役トリエン / ポリエン / 海洋天然物 / ヘテロアセン / 共役ポリエン / ボロネート / ルテニウム / 電子移動 / 酸化還元特性 / 鎖状交差二量化 / ルテニウム錯体 / 分子ワイヤ / 位置選択性 / 酸化的カップリング機構 / デカペンタエン / ワンポット合成 / 位置選択性制御 / 側鎖のない共役ポリエン / π共役型縮環系有機半導体物質 / 共役ポリエニル置換基の導入法 / 共役テトラエン / 反応性官能基 / 反応機構 / 共役トリエン / 内部側鎖のない共役ポリエン / ペンタセン / 合成化学
Outline of Final Research Achievements

In this study, a novel catalytic reaction between conjugated dienes and alkynes catalyzed by Ru(0) complexes to form conjugated trienes and tetraenes was established. In particular, following reactions between the boron-substituted conjugated dienes and alkynes, cross-coupling reactions led to the total synthesis of the marine natural product Navenone B and the formal synthesis of the apoptosis control molecule Bongkrekic acid. In addition, a novel method for the synthesis of polysubstituted pyrroles was discovered, in which the reaction of an iminoalkyne with a conjugated diene leads to the formation of a conjugated triene with a nitrogen substituent followed by aromatization. The reaction was also found to be effective for the π-conjugation extension of organic semiconducting materials and other materials.

Academic Significance and Societal Importance of the Research Achievements

本研究は学術的には新規な共役ポリエン、非共役ポリエン分子の構築法を確立するとともにホウ素などの反応性置換基を導入してその合成的有用性を実現し、実際に天然物や電子材料などの合成に適用した。国際的学術誌に合計13報の論文発表をおこなった。また、2件の特許出願を行いJSTの支援によりいずれも各国移行を伴う国際特許となった。学生や一般社会人に向けた化学雑誌への掲載2件、化学ポータルサイトChem-Stationへの掲載2件、新聞報道4件、本研究に関わる企業との共同研究1件、国際共同研究3件など社会的、国際的にも意義ある研究を実施した。

Report

(6 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (65 results)

All 2022 2021 2020 2019 2018 2017 Other

All Int'l Joint Research (7 results) Journal Article (18 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 18 results,  Open Access: 2 results) Presentation (32 results) (of which Int'l Joint Research: 7 results,  Invited: 4 results) Remarks (4 results) Patent(Industrial Property Rights) (4 results) (of which Overseas: 2 results)

  • [Int'l Joint Research] National Taiwan Normal University(その他の国・地域 中華民国(台湾))

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] Toront Metropolitan University/Ryerson University(カナダ)

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] Mount Allison University/Ryerson University(カナダ)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Mount Allison University(カナダ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] マウントアリソン大学(カナダ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] 国立台湾師範大学(中華民国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] オーストラリア国立大学(オーストラリア)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Dibenzo[d,d0]benzo[2,1-b:3,4-b0]difurans with Extended p-Conjugated Chains: Synthetic Approaches and Properties2022

    • Author(s)
      Masafumi Hirano, Harumi Okada, Chikara Hayasaka, Nobuyuki Komine, Sayori Kiyota, Koji Nakano
    • Journal Title

      New Journal of Chemistry

      Volume: 46 Issue: 3 Pages: 1003-1017

    • DOI

      10.1039/d1nj04796e

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru(0)-Catalyzed Regioselective Synthesis of Borylated-1,4- and -1,5-Diene Building Blocks2022

    • Author(s)
      Shione Okazaki, Keita Shimada, Nobuyuki Komine, Masafumi Hirano
    • Journal Title

      Organometallics

      Volume: 41 Issue: 4 Pages: 390-411

    • DOI

      10.1021/acs.organomet.1c00615

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru(0)-Catalyzed Synthesis of Conjugated Iminotrienes and Subsequent Intramolecular Cyclization Giving Polysubstituted Pyrroles2022

    • Author(s)
      Shinnosuke Kurita, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 16 Pages: 2973-2977

    • DOI

      10.1021/acs.orglett.2c00773

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru(0)-Catalyzed Synthesis of Borylated-Conjugated Triene Building Blocks by Cross-Dimerization and Their Use in Cross-Coupling Reactions2021

    • Author(s)
      Ayumi Kuramochi, Nobuyuki Komine, Sayori Kiyota, Masafumi Hirano
    • Journal Title

      Bulletin of Chemical Society of Japan

      Volume: 94 Issue: 8 Pages: 2113-2132

    • DOI

      10.1246/bcsj.20210163

    • NAID

      130008087862

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New strategy for synthesising conjugated hexatrienylferrocenes via cross-dimerisation2021

    • Author(s)
      Sawasaki Asami, Komine Nobuyuki, Kawauchi Susumu, Hirano Masafumi
    • Journal Title

      New Journal of Chemistry

      Volume: - Issue: 33 Pages: 14988-14998

    • DOI

      10.1039/d0nj05413e

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity2021

    • Author(s)
      Masafumi Hirano, Shuhei Machida, Ryota Abe, Takuya Mishina, Nobuyuki Komine, Hsyueh-Liang Wu
    • Journal Title

      Organometallics

      Volume: 40 Issue: 20 Pages: 3370-3388

    • DOI

      10.1021/acs.organomet.1c00368

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 生物活性物質の骨格多様化と合成工程短段階化に関する新技術(特集:創薬を支える独創的な技術開発)2021

    • Author(s)
      平野雅文
    • Journal Title

      月刊「化学工業」

      Volume: 72 Pages: 21-27

    • NAID

      40022453459

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ligand-Controlled Regiodivergent Hydrosilylation of Conjugated Dienes Catalyzed by Mono(phosphine)palladium(0) Complexes2020

    • Author(s)
      Komine Nobuyuki, Mitsui Tatsuo, Kikuchi Shu, Hirano Masafumi
    • Journal Title

      Organometallics

      Volume: 39 Issue: 24 Pages: 4510-4524

    • DOI

      10.1021/acs.organomet.0c00597

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate: Synchrotron Radiation Sheds Light on the Cu Cycle Mechanism2020

    • Author(s)
      Kanazawa, Yuki; Mitsudome, Takato; Takaya, Hikaru; Hirano, Masafumi
    • Journal Title

      ACS Catalysis

      Volume: 10 Issue: 10 Pages: 5909-5919

    • DOI

      10.1021/acscatal.0c00918

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An insight into regioselectivity in the transformation through a ruthenacycle2020

    • Author(s)
      Kiyota Sayori、Hirano Masafumi
    • Journal Title

      New Journal of Chemistry

      Volume: 44 Issue: 5 Pages: 2129-2145

    • DOI

      10.1039/c9nj04880d

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic cross-dimerisation giving reactive borylated polyenes toward cross-coupling2019

    • Author(s)
      Hirano Masafumi、Kuramochi Ayumi、Shimada Keita、Komine Nobuyuki、Kiyota Sayori、Westcott Stephen A.
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 71 Pages: 10527-10530

    • DOI

      10.1039/c9cc05930j

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Recent advances of achiral and chiral diene ligands in transition-metal catalyses2019

    • Author(s)
      Hirano Masafumi、Komine Nobuyuki、Arata Eri、Gridneva Tatiana、Hatori Atsuya、Kaizawa Naoki、Kamakura Kohei、Kuramochi Ayumi、Kurita Shinnosuke、Machida Shuhei、Okada Harumi、Sawasaki Asami、Uchino Takumi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 37 Pages: 150924-150924

    • DOI

      10.1016/j.tetlet.2019.07.015

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Recent Advances in the Catalytic Linear Cross-Dimerizations2019

    • Author(s)
      Hirano Masafumi
    • Journal Title

      ACS Catalysis

      Volume: 9 Issue: 2 Pages: 1408-1430

    • DOI

      10.1021/acscatal.8b04676

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] In Situ Routes to Catalytically Active Ru(0) Species by Reduction of Readily Available, Air-Stable Precursors2018

    • Author(s)
      Hirano Masafumi、Kobayashi Hideyuki、Ueda Takao、Hiroi Yuki、Abe Ryota、Komine Nobuyuki、Colebatch Annie L.、Bennett Martin A.
    • Journal Title

      Organometallics

      Volume: 37 Issue: 7 Pages: 1092-1102

    • DOI

      10.1021/acs.organomet.7b00882

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of and Catalytic Linear Cross-Dimerizations by an Electron-Deficient Cyclic Diene Complex of Ruthenium(0)2018

    • Author(s)
      Hirano Masafumi、Tanaka Yukino、Komine Nobuyuki
    • Journal Title

      Organometallics

      Volume: 37 Issue: 22 Pages: 4173-4176

    • DOI

      10.1021/acs.organomet.8b00645

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 電子材料、医薬品の鍵構造をワンポット合成2018

    • Author(s)
      平野雅文
    • Journal Title

      月刊「化学」

      Volume: 73 Pages: 12-16

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru(0)-Catalyzed Straightforward Synthesis of Conjugated Tetraenes: An Approach using Two Internal Alkynes with 1,3-Butadiene2018

    • Author(s)
      Kiyota Sayori、Hirano Masafumi
    • Journal Title

      Organometallics

      Volume: 37 Issue: 2 Pages: 227-234

    • DOI

      10.1021/acs.organomet.7b00801

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 電子材料、医薬品の鍵構造をワンポット合成 ー ブタジエンとアセチレン誘導体でつくる共役テトラエン2018

    • Author(s)
      平野 雅文
    • Journal Title

      月刊「化学」

      Volume: 73, Vol. 5 Pages: 12-16

    • NAID

      40021554688

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 新規な鎖状交差二量化反応の創成と電子材料物質・天然物合成への展開2022

    • Author(s)
      平野 雅文
    • Organizer
      新化学技術推進協会 先端化学・材料技術部会 講演会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 鎖状交差二量化反応による共役イミノトリエンの生成とそれらを中間体とする多置換ピロールの新規合成2022

    • Author(s)
      栗田 真之介、清田 小織、小峰 伸之、平野 雅文
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 位置およびエナンチオ選択的鎖状交差二量化反応によるキラルシリル化スキップジエンの合成2022

    • Author(s)
      橋本 莉奈、清田 小織、小峰 伸之、平野 雅文
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ジボリル化非共役ジエンをビルディングブロックとする位置選択的構造導入2021

    • Author(s)
      岡﨑 汐音, 小峰 伸之, 平野 雅文
    • Organizer
      第10回JACI/GSCシンポジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] 1,3-エンインと1,3-ジエンを用いた共役テトラエンの直截的合成2021

    • Author(s)
      前川 可南子, 小峰 伸之, 清田 小織, 平野 雅文
    • Organizer
      第10回JACI/GSCシンポジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] エナンチオ選択的交差二量化反応によるボリル化スキップジエンの合成2021

    • Author(s)
      内野 匠, 小峰 伸之, 平野 雅文
    • Organizer
      第10回JACI/GSCシンポジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] 交差二量化によるホウ素化共役トリエンビルディングブロックの合成とクロスカップリング反応への応用2021

    • Author(s)
      平野 雅文、倉持 歩実、小峰 伸之、清田 小織
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] エナンチオ選択的交差二量化反応によるキラルボリル化スキップジエンの合成2021

    • Author(s)
      内野 匠、小峰 伸之、平野 雅文
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 交差二量化反応によるケイ素置換共役トリエンビルディングブロックの合成とクロスカップリング反応への応用2021

    • Author(s)
      荒田 恵理、小峰 伸之、清田 小織、平野 雅文
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 非対称1,6-ジボリル-1,5-ジエンの直截的合成と 位置選択的クロスカップリングへの応用2021

    • Author(s)
      岡﨑 汐音, 小峰 伸之, 平野 雅文
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 1,3-エンインと1,3-ジエンを用いた共役テトラエンの直截的合成2021

    • Author(s)
      前川 可南子, 小峰 伸之, 清田 小織, 平野 雅文
    • Organizer
      第128回触媒討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 鎖状交差二量化によるボリル化ジエンの触媒的合成と応用2020

    • Author(s)
      平野雅文、島田啓太、小峰伸之
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Ru-Catalyzed Cross-Dimerizations: The Historical Background and the Future2020

    • Author(s)
      Masafumi Hirano
    • Organizer
      SUSTech Symposium 2020
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] シリル化共役トリエンの触媒的合成とプロト脱シリル化反応2019

    • Author(s)
      平野 雅文・齋藤 諒・小峰伸之・清田小織
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Catalytic Synthesis of Reactive Skipped Dienylboronate Esters and Their Applications to Building Blocks2019

    • Author(s)
      Keita Shimada, Nobuyuki Komine, Sayori Kiyota, and Masafumi Hirano
    • Organizer
      第69回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Direct Synthesis of Conjugated Polyenes Having a Reactive Boronate and Their Synthetic Application2019

    • Author(s)
      Ayumi Kuramochi, Sayori Kiyota, Nobuyuki Komine, and Masafumi Hirano
    • Organizer
      第69回有機金属化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Ru(0)-Catalyzed Chemo-, Regio- and Enantioselective Linear Cross-Dimerization: From Mechanism to Applications2019

    • Author(s)
      Masafumi Hirano
    • Organizer
      102nd Canadian Chemistry Conference and Exhibition
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 非対称内部アルキンと共役ジエンを用いた共役トリエンの触媒的合成:位置選択性に及ぼす電子的及び立体的置換基効果2019

    • Author(s)
      清田 小織・平野 雅文
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 反応活性なホウ素置換基を有するスキップジエンビルディングブロックの触媒的合成2019

    • Author(s)
      島田 恵太・清田 小織・小峰 伸之・平野 雅文
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 反応活性なホウ素置換基を有する共役トリエンビルディングブロックの触媒的合成2019

    • Author(s)
      倉持 歩実・清田 小織・小峰 伸之・平野 雅文
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] キラルビシクロヘプタジエン)ルテニウム(0)錯体を触媒とする 共役ジエンとアクリル酸メチルとの触媒的不斉交差二量化反応2019

    • Author(s)
      田中 雪乃・小峰 伸之・Hsyueh-Liang Wu・平野 雅文
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Direct Coupling of Nonprotected Alkynylboronate with Conjugated Dienes2018

    • Author(s)
      Ayumi Kuramochi, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct Coupling of Conjugated Dienes with Unsymmetric Internal Alkynes and the Regioselectivity Control2018

    • Author(s)
      Sayori Kiyota, Ryo Saito, Seoyoung In, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and Protodesilylation of Silyl-substituted Conjugated Trienes by Direct Coupling of Silylalkynes with Conjugated Dienes2018

    • Author(s)
      Ryo Saito, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Ru(0)錯体触媒を用いた1,2-ジメチレンシクロヘキサンと置換アルケン間の 鎖状交差二量化反応2018

    • Author(s)
      島田 恵太・小峰 伸之・平野 雅文
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Ru(0)-Catalyzed Direct Synthesis of Lineaer Conjugated Tetraenes2018

    • Author(s)
      Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      XXVIII International Conference on Organometallic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct Approach to Conjugated Polyenes and the Mechanistic Insights2018

    • Author(s)
      Masafumi Hirano, Sayori Kiyota, Ryo Saito, Seonyoung In, Nobuyuki Komine
    • Organizer
      XXVIII International Conference on Organometallic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Ru(0)-Catalyzed Synthesis of Conjugated Trienes and Tetraenes by Direct Coupling of Conjugated Dienes with Internal Alkynes2018

    • Author(s)
      Sayori Kiyota, Seonyoung In, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      日本化学会第98春季年会(英語講演)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 共役ジエンとシリル置換アルキンの直接カップリングによる共役トリエンの合成とプロト脱シリル化反応2018

    • Author(s)
      齋藤 諒、小峰伸之、平野雅文
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Recent Development on Ru(0)-Catalyzed Direct Synthesis of COnjugated Polyene Molecules2018

    • Author(s)
      Masafumi Hirano
    • Organizer
      TMU-PetroMat Joint Mini-Symposium on Catalysis and Advanced Materials
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ru(0)錯体触媒によるベンゼン環結合型共役トリエン、ヘキサエンおよびノナエンの直截的合成2017

    • Author(s)
      平野雅文、齋藤 諒、清田小織、小峰伸之
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ru(0)-Catalyzed Direct Coupling of Di- and Triynylbenzenes with Conjugated Dienes giving Benzene-fused Hexaenes and Nonaene2017

    • Author(s)
      Ryo Saito, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
    • Organizer
      OMCOS 19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Remarks]

    • URL

      http://web.tuat.ac.jp/~hirano/kohrc/researchtutorial_frame.html#00

    • Related Report
      2021 Annual Research Report
  • [Remarks] Research 研究概要

    • URL

      http://web.tuat.ac.jp/~hirano/kohrc/researchtutorial_frame.html#00

    • Related Report
      2020 Annual Research Report
  • [Remarks] 研究概要

    • URL

      http://web.tuat.ac.jp/~hirano/kohrc/researchtutorial_frame.html#00

    • Related Report
      2019 Annual Research Report
  • [Remarks]

    • URL

      http://web.tuat.ac.jp/~hirano/kohrc/researchtutorial_frame.html#00

    • Related Report
      2018 Annual Research Report
  • [Patent(Industrial Property Rights)] Boron-containing conjugated polyene compound, method for producing same, and method for producing conjugated polyene compound2019

    • Inventor(s)
      Masafumi Hirano et al.
    • Industrial Property Rights Holder
      Masafumi Hirano et al.
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Acquisition Date
      2020
    • Related Report
      2020 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] Boron-containing conjugated polyene compound, method for producing same, and method for producing conjugated polyene compound2019

    • Inventor(s)
      Masafumi Hirano et al.
    • Industrial Property Rights Holder
      Masafumi Hirano et al.
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 含ホウ素化合物及びその製造方法2019

    • Inventor(s)
      平野雅文、島田恵太、小峰伸之、清田小織
    • Industrial Property Rights Holder
      東京農工大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-021791
    • Filing Date
      2019
    • Related Report
      2018 Annual Research Report
  • [Patent(Industrial Property Rights)] 含ホウ素ポリエン化合物及びその製造方法2018

    • Inventor(s)
      平野雅文、倉持歩実、小峰伸之、清田小織
    • Industrial Property Rights Holder
      東京農工大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-174979
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report

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Published: 2017-04-28   Modified: 2023-01-30  

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