Development of Synthetic Method of Rotaxane Incorporated with SPM toward Constructing Functional Molecules

• Project/Area Number: 21750050
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Tokyo University of Science
• Principal Investigator: YAMASAKI Ryu Tokyo University of Science, 理学部, 助教 (90453844)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 超分子化学 / ナノ材料 / 分子機械 / 有機金属化学 / 有機金属

Research Abstract

Rotaxane is one of the interlocked compound which composed with macrocycle and axis which is inseparable without breaking bonds. To functionalize these interlocked molecules, I envisioned to use a stiff macrocycle, SPM, as the macrocycle. As a result, I succeeded to synthesize the unsymmetrical SPM molecule and attempted to prepare rotaxane via reaction mediated by this macrocycle.

Research Products

• [Journal Article] Synthesis and Structure of Dinuclear Silver (I) and Palladium (II) Complexe of 2,7-Bis(methylene) naphthalene-Bridged Bis-N-Heterocyclic Carbene Ligands (2011)
  • Author(s): Shinichi Saito, Mitsuya Saika, Ryu Yamasaki, Isao Azumava, Hvuma Masu.
  • Journal Title: Organometallics 30巻 Pages: 1366-1373
  • Peer Reviewed
• [Journal Article] Synthesis and Structure of Dinuclear Silver(I) and Palladium(II) Complexes of 2,7-Bis(methylene)naphthalene-Bridged Bis-N-Heterocyclic Carbene Ligands (2011)
  • Author(s): 斎藤慎一
  • Journal Title: ORGANOMETALLICS Volume: 30 Pages: 1366-1373
  • Peer Reviewed
• [Journal Article] Synthesis and Characterization of Silver and Palladium Complexes with Xanthene Based N-Heterocyclic Carbene-Oxazoline Ligands (2010)
  • Author(s): Takeshi Makino, Ryu Yamasaki, Isao Azumaya, Hyuma Masu, Shinichi Saito
  • Journal Title: Organometallics 29巻 Pages: 6291-6297
  • Peer Reviewed
• [Journal Article] 環をつかった化学のマジック (2010)
  • Author(s): 山崎龍、斎藤慎一
  • Journal Title: 化学 65巻 Pages: 72-73
• [Journal Article] Ring expansion reactions of ethyl cyclopropylideneacetate and benzosila- cyclobutenes: formal σ bond cross metathesis (2010)
  • Author(s): Shinichi Saito, Takahiro Yoshizawa, Shinya Ishigami, Rvu Yamasaki
  • Journal Title: Tetrahedron Letters 51巻 Pages: 6028-6030
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed [3+2+2] Cycloaddition of Ethyl Cyclopropylidene- acetate and Heteroatom-Substituted Alkynes : Application to Selective Three-Component Reaction with 1,3- Diynes (2010)
  • Author(s): Ryu Yamasaki, Natsuki Terashima, Ikuo Sotome, Shunsuke Komagawa, Shinchi Saito
  • Journal Title: Journal of Organic Chemistry 75巻 Pages: 480-483
  • Peer Reviewed
• [Journal Article] Selective Synthesis of Eight-membered Cyclic Ureas by the [6+2] Cycloaddition Reaction of 2-Vinyl- azetidines and Electron-Deficient Isocyanates (2010)
  • Author(s): Shunsuke Koya, Kenichi Yamanoi, Ryu Yamasaki, Isao Azumaya, Hyuma Masu, Shinichi Saito
  • Journal Title: Organic Letters 11巻 Pages: 5438-5441
  • Peer Reviewed
• [Journal Article] Thermal and catalytic isomerization of exomethylenecycloheptadienes. Experimental and theoretical studies. (2010)
  • Author(s): Yukiko Fukusaki, Jun Miyazaki, Isao Azumaya, Kosuke Katagiri, Shunsuke, Komagawa, Ryu Yamasaki, Shinichi Saito.
  • Journal Title: Tetrahedron 65巻 Pages: 10631-10636
  • Peer Reviewed
• [Journal Article] 環をつかった化学のマジック (2010)
  • Author(s): 山崎龍
  • Journal Title: 月刊 化学10月号 Volume: 65 Pages: 72-73
• [Journal Article] Synthesis and Characterization of Silver and Palladium Complexes with Xanthene Based N-Heterocyclic Carbene-Oxazoline Ligands (2010)
  • Author(s): 牧野剛士
  • Journal Title: ORGANOMETALLICS Volume: 29 Pages: 6291-6297
  • Peer Reviewed
• [Journal Article] Ring expansion reactions of ethyl cyclopropylideneacetate and benzosilacyclobutenes : formal δ bond cross metathesis. (2010)
  • Author(s): 斎藤慎一
  • Journal Title: TETRAHEDRON LETTERS Volume: 51 Pages: 6028-6030
  • Peer Reviewed
• [Journal Article] Ni-Catalyzed [3+2+2] Cycloaddition of ethyl cyclopropylideneacetate and Heteroatom-Substituted Alkynes : Application to Selective Three-Component Reaction with 1,3-diynes (2010)
  • Author(s): 山崎龍
  • Journal Title: Journal of Organic Chemistry VOL 75 Pages: 480-483
  • Peer Reviewed
• [Journal Article] Synthesis of Nine-Membered Carbocycles by the [4+3+2] Cycloaddition Reaction of Ethyl Cyclopropylideneacetate and Dienynes (2010)
  • Author(s): 斎藤慎一
  • Journal Title: Angewandte Chemie International Edition VOL 49 Pages: 1830-1833
  • Peer Reviewed
• [Journal Article] Synthesis of Nine-membered Carbocycles by the [4 + 3 + 2] Cycloaddition Reactn of Ethyl Cyclopropylideneacetate and Dienynes (2009)
  • Author(s): Shinichi Saito, Kyotaro Maeda, Ryu Yamasaki, Takuya Kitamura, Minami Nakagawa, Korehito Kato, Isao Azumaya, Hyuma Masu
  • Journal Title: Angewandte Chemie-International Edition. 49巻 Pages: 1830-1833
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Intermolecular [3 + 2 + 2] Cocyclization of Ethyl Cyclopropylidene- acetate and Alkynes. (2009)
  • Author(s): Shinsuke Komagawa, Kouhei Takeuchi, Ikuo Sotome, Isao Azumaya, Hyuma Masu, Ryu Yamasaki, Shinichi Saito.
  • Journal Title: Synthesis of Seven-Membered Carbocycles、Journal of Organic Chemistry. 74巻 Pages: 3323-3329
  • Peer Reviewed
• [Journal Article] Synthesis, Structure and Catalytic Activity of Macrocyclic NHC Pd Pincer Complexes (2009)
  • Author(s): Noriaki Watarai, Hiroyasu Kawasaki, Isao Azumaya, Ryu Yamasaki, Shinichi Saito
  • Journal Title: HETEROCYCLES 79巻 Pages: 531-548
  • Peer Reviewed
• [Journal Article] Ni-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylidene- acetate and 1,3-diynes. Application to the three-component cycloaddition. (2009)
  • Author(s): Ryu Yamasaki, Ikuo Sotome, Shunsuke Komagawa, Isao Azumaya, Hyuma Masu, Shinichi Saito
  • Journal Title: Tetrahedron Letters. 50巻 Pages: 1143-1145
  • Peer Reviewed
• [Journal Article] Selective Synthesis of Eight-Membered Cyclic Urea by the [6+2] Cycloaddition Reaction of 2-Vinylazehdine and Electron-Deficient Isocyanates (2009)
  • Author(s): 小矢俊輔
  • Journal Title: Organic Letters VOL 11 Pages: 5438-5441
  • Peer Reviewed
• [Journal Article] Thermal and catalytic isomerization of exomethylenecycloheptadienes. Experimental and theoretical studies (2009)
  • Author(s): 福崎有希子
  • Journal Title: Tetrahedron VOL 65 Pages: 10631-10636
  • Peer Reviewed
• [Journal Article] Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3+2+2] Cocyclization. Application to the Synthesis of Polycyclic Compounds (2009)
  • Author(s): 駒川晋輔
  • Journal Title: Journal of Organic Chemistry VOL 74 Pages: 3323-3329
  • Peer Reviewed
• [Journal Article] Synthesis, Structure and Catalytic Activity of Macrocyclic NHC Pd Pincer Complexes (2009)
  • Author(s): 渡来則明
  • Journal Title: Heterocycles VOL 79 Pages: 531-548
  • Peer Reviewed
• [Presentation] [4+3+2]型環化付加反応におけるアミド結合を有するジニンインの配座と収率の関係 (2011)
  • Author(s): 藤田哲嗣
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(横浜)
  • Year and Date: 2011-03-29
• [Presentation] 効率的な金属配位可能なSPM合成法開発と触媒反応への応用 (2011)
  • Author(s): 山崎龍
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(横浜)
  • Year and Date: 2011-03-28
• [Presentation] 芳香族ビニログ性アミドの合成と物性 (2011)
  • Author(s): 池田宏和
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(横浜)
  • Year and Date: 2011-03-28
• [Presentation] フェナントロリン-銅錯体を反応活性体として利用したインターロック化合物の合成研究 (2011)
  • Author(s): 山崎龍
  • Organizer: 第11回リング・チューブ超分子研究会シンポジウム
  • Place of Presentation: 東京工業大学(大岡山)
  • Year and Date: 2011-03-11
• [Presentation] [4+3+2]型環化付加反応におけるアミド結合を有するジエンインの配座と収率の関係 (2011)
  • Author(s): 藤田哲嗣・中川みなみ・山崎龍・斉藤慎一
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
• [Presentation] 効率的な金属配位可能なSPM合成法開発と触媒反応への応用 (2011)
  • Author(s): 山崎龍・重藤敦嗣・斎藤慎一
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
• [Presentation] 芳香族ビニログ性アミドの合成と物性 (2011)
  • Author(s): 池田宏和・山崎龍・桝飛雄真・東屋功・斎藤慎一
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
• [Presentation] フェナントロリン-銅錯体を反応活性体として利用したインターロック化合物の合成研究 (2011)
  • Author(s): 山崎龍、佐藤雄太、高橋英子、中薗和子、斎藤慎一
  • Organizer: 第11回リング・チューブ超分子研究会シンポジウム
  • Place of Presentation: 東京工業大学
• [Presentation] Synthesis of medium-sized rings by the Ni-catalyzed cycloaddition reactions (2010)
  • Author(s): 斎藤慎一
  • Organizer: 2010 International Chemical Congress of Pacific Basin Soriekies
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-18
• [Presentation] Synthesis of monocyclic compounds by the nickel-catalyzed [4+3+2] cycloaddition (2010)
  • Author(s): 加藤惟人
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-18
• [Presentation] Synthesis of seven-menbered cyclic ureas by the [5+2] cycloaddition reaction of 2-vinylaziridines and electron-deficient isocyanates (2010)
  • Author(s): 管野恵理
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-17
• [Presentation] Synthesis and catalytic activity of pyridine-incorporated SPM-metal complex (2010)
  • Author(s): 重藤敦嗣
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-17
• [Presentation] Synthesis of interlocked compounds by the reaction of macrocycle-metal complexes (2010)
  • Author(s): 山崎龍
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2010-12-15
• [Presentation] [5+2] Cycloaddition Reaction of 2-Vinylaziridines and Electron-deficient Isocyanates : the Effert of the Stereochemistry on the Reaction (2010)
  • Author(s): 管野恵理
  • Organizer: 8th Scmposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理科大学、東京
  • Year and Date: 2010-12-01
• [Presentation] ビニルアジリジンと電子欠乏性イソシアネートとの[5+2]環化付加反応 (2010)
  • Author(s): 管野恵理
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 東京理科大学、東京
  • Year and Date: 2010-11-01
• [Presentation] Diaetereoselective Ni-Catalyzed [4+3+2] Cocyclization Reaction between Dienyne and Methylenecyclopropane. (2010)
  • Author(s): 山崎龍
  • Organizer: 7th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理科大学、東京
  • Year and Date: 2010-09-29
• [Presentation] Chirality of Bidentate Palladium Complexes with Xanthene Framework : Chiral vs.Achiral Conformation (2010)
  • Author(s): 斎藤慎一
  • Organizer: 7th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理科大学、東京
  • Year and Date: 2010-09-29
• [Presentation] ニッケル触媒存在下におけるエチルシクリプロピリデンアセテートとベンゾシラシクロブテンの環拡大反応 (2010)
  • Author(s): 斎藤慎一
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学、東京
  • Year and Date: 2010-09-16
• [Presentation] Preparation of Interlocked Compounds by Macrocyclic Phenanthroline-Cu Complexes as the Platform of Coupling Reaction (2010)
  • Author(s): 山崎龍
  • Organizer: Post 5th International Symposium on Macrocyclic and Supramolecular Chemistry &第6回ホストゲスト化学シンポジウム
  • Place of Presentation: 大阪国際交流センター、大阪
  • Year and Date: 2010-06-12
• [Presentation] Preparation of Interlocked Compounds by Macrocyclic Phenanthroline-Cu Complexes as the Platform of Coupling Reaction (2010)
  • Author(s): 山崎龍
  • Organizer: 5th International Symposium on Macrocyclic & Supramolecular Chemistry
  • Place of Presentation: 奈良県新公会堂、奈良
  • Year and Date: 2010-06-07
• [Presentation] Synthesis of medium-sized rings by the Ni-catalyzed cycloaddition reactions (2010)
  • Author(s): Ryu Yamasaki, Shinichi Saito
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ハワイ
• [Presentation] Synthesis of monocyclic compounds by the nickel-catalyzed [4+3+2] cycloaddition (2010)
  • Author(s): Korehito Kato, Ryu Yamasaki, Shinichi Saito
  • Organizer: 2010 International Chemal Congress of Pacifc Basin Societies
  • Place of Presentation: ハワイ
• [Presentation] Synthesis and catalytic activit of pyridine-incorporated SPM-metal complex (2010)
  • Author(s): Atsushi Shigeto, Shinchi Saito, Ryu Yamasaki
  • Organizer: 2010 International Chemical Congss of Pacific Basin Soeties
  • Place of Presentation: ハワイ
• [Presentation] Synthesis of seven-menbered cyclic ureas by the [5+2] cycloaddition reaction of 2-vinylaziridines and electron-deficient isocyanates (2010)
  • Author(s): Eri Kanno, Shunsuke Koya, Kenichi Yamanoi, Ryu Yamasaki, Shinichi Saito
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ハワイ
• [Presentation] Synthesis of interlocked compounds by the reaction of macrocycle-metal complexes (2010)
  • Author(s): Ryu Yamasaki, Shinichi Saito.
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ハワイ
• [Presentation] [5+2] Cycloaddition Reaction of 2-Vinylaziridines and Electron-deficient Isocyanes : the Efct of the Stereochemistry on the Reaction (2010)
  • Author(s): Eri Kanno, Shunsuke Koya, Kenichi Yamanoi, Ryu Yamasaki, Shinichi Saito
  • Organizer: 8th Symposium on Chemial Apprchesto Chirality
  • Place of Presentation: 東京理科大学
• [Presentation] ビニルアジリジンと電子欠乏性イソシアネートとの[5+2]環化付加反応 (2010)
  • Author(s): 管野恵理、山野井健一、小矢俊亮、山崎龍、斎藤慎一
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋
• [Presentation] Diastereoselective Ni-Catalyzed [4+3+2] Cocyclization Reaction between Dienyne and Methylenecyclopropane (2010)
  • Author(s): Ryu Yamasaki, Takuya Kitamura, Kyotaro Maeda, Minami Nakagawa, Korehito Kato, Masu Hyuma, Isao Azumaya, Shinichi Saito
  • Organizer: 7th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理科大学
• [Presentation] ニッケル触媒存在下におけるエチルシクリプロピリデンアセテートとベンゾシラシクロブテンの環拡大反応 (2010)
  • Author(s): 斎藤慎一、山崎龍、石神慎也、吉澤孝弘
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学
• [Presentation] Preparation of Interlocked Compounds by Macrocyclic Phenantroline-Cu Complees as the Platform of Coupling Reaction (2010)
  • Author(s): Ryu Yamasaki, Yuta Sato, Eiko Takahashi, Kazuko Nakazono, Shinichi Saito
  • Organizer: Post 5th International Symposium on Macrocyclic and Supramolecular Chemistry & 第ホストゲスト化シンポジウム
  • Place of Presentation: 大阪
• [Presentation] Preparation of Interlocked Compounds by Macrocyclic Phenantroline-Cu Complees as the Platform of Coupling Reaction (2010)
  • Author(s): Ryu Yamasaki, Yuta Sato, Eiko Takahashi, Kazuko Nakazono, Shinichi Saito
  • Organizer: 5th International Symposium on Macrocyclic & Supramolecular Chemistry
  • Place of Presentation: 奈良
• [Presentation] Ni触媒によるジエンインとメチレンシクロプロパンとの[4+3+2]型環化付加反応:ジエンインの構造の重要性 (2010)
  • Author(s): 山崎龍、前田京太郎、北村卓也、中川みなみ、加藤惟人、桝飛雄真、東屋功、斉藤慎一
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学
• [Presentation] Ni触媒存在下における[4+3+2]型環化付加反応を利用した単環性9員環化合物の合成 (2010)
  • Author(s): 加藤惟人、山崎龍、斎藤慎一
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学
• [Presentation] Synthesis and Catalytic Activity of Macrocyclic BINOL Derivatives (2009)
  • Author(s): Natsuko Ichihara
  • Organizer: 6th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理科大学
  • Year and Date: 2009-11-25
• [Presentation] Ni触媒によるジエンインと電子欠乏性メチレンシクロプロパンとの間の[4+3+2]型環化付加反応 (2009)
  • Author(s): 山崎龍
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 同志社大学
  • Year and Date: 2009-09-11
• [Presentation] Synthesis and Catalytic Activity of Macrocyclic BINOL Derivatives (2009)
  • Author(s): Natsuko Ichihara, Eiko Takahashi, Nobutaka Ueda, Ryu Yamasaki, Shinichi Saito
  • Organizer: 6th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: 東京理大学
• [Presentation] ジエンインを用いた[4+3+2]型環化付加反応におけるジエン部位の置換基効果 (2009)
  • Author(s): 北村卓也, 前田京太郎, 山崎龍, 斎藤慎一, 桝飛雄真、東屋功
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
• [Presentation] Ni 触媒によるジエンインと電子欠乏性メチレンシクロプロパンとの間の[4+3+2]型環化付加反応 (2009)
  • Author(s): 山崎龍、前田京太郎、中川みなみ、北村卓也、加藤惟人、東屋功、桝飛雄真、斎藤慎一
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 同志社大学
• [Presentation] Nickel-Catayzed [4+2] Cocyclization of Ethyl Cloprolideneacete Dienynes (2009)
  • Author(s): Shinichi Saito, Kyotaro Maeda, Ryu Yamasaki, Minami Nakagawa, Takuya Kitamura, Korehito Kato
  • Organizer: 15th IUPAC Symposium on Organomallic Chemistry directed trds Organic Sesis
  • Place of Presentation: Glasow
• [Book] 化学事典(共著、共同編集) (2010)
  • Author(s): 斎藤慎一, 山崎龍, 他
• [Remarks]
  • URL: http://www.sut.ac.jp/ridai/doc/ji/RIJIA01Detail.php?act=nam&kin=ken&diu=A21073
• [Remarks]
  • URL: http://www.tus.ac.jp/ridai/doc/ji/RIJIA01Detail.php?act=nam&kin=ken&diu=A21073