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KAKEN_15H05839seika.pdf
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平面多環芳香族分子の生体分子複合化に基づいた新機能創製
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ヘイメン タカン ホウコウゾク ブンシ ノ セイタイ ブンシ フクゴウカ ニ モトズイタ シンキノウ ソウセイ
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Heimen takan hōkōzoku bunshi no seitai bunshi fukugōka ni motozuita shinkinō sōsei
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Development of new functions based on connection of biomolecular with planar polycyclic aromatic molecules
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垣内, 史敏
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カキウチ, フミトシ
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Kakiuchi, Fumitoshi
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慶應義塾大学・理工学部 (矢上) ・教授
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Research team head
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科研費研究者番号 : 70252591
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2020
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科学研究費補助金研究成果報告書
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2019
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本研究では、C-HとC-O結合を利用してアントラキノン骨格に異なるアリール基の導入し、それらの多環芳香族炭化水素 (PAH) へ変換と、合成したPAHの溶液中での挙動を利用して薬剤などの生理活性物質を効率的に機能させる手法の開発を目指して検討した。ルテニウム触媒を用いた1-メトキシアントラキノンとアリールボロン酸エステルとの反応を行い、カルボニル基のオルト位4つのうち1つのみが他と異なるテトラアリールアントラキノンを合成した。さらに、カルボニル基の変換、Scholl反応で脱水素芳香族化を行い、ホルミル基を1つ持つテトラベンゾコロネン誘導体を合成した。この化合物は溶液中で目的の集積化挙動を示した。
Various polycyclic aromatic hydrocarbons (PAHs) have been synthesized for utilization as functionalized organic materials and a large number of efforts have been paid for development of their efficient synthetic methods. Our group has been working on the efficient synthesis of polycyclic aromatic hydrocarbons (PAHs) based on our ruthenium-catalyzed C-H and C-O arylations of aromatic ketones. In this study we have applied this strategy to efficient synthesis of tetrabenzo[a,d,j,m]coronene (TBC) derivatives having a readily transformable formyl group.
The chemoselective C-O arylation of 1-methoxyanthraquinone with an arylboronate having an acetal group at a para position proceeded using RuH2(CO)(PPh3)3 as a catalyst to give a 1-arylanthraquinone. Subsequent C-H triarylation with another arylboronate provided tetraarylanthraquinone with one acetal group. Conversion of carbonyl oxygens to methylidenes, followed by Scholl reaction, afforded the TBC derivative bearing a formyl group.
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研究種目 : 新学術領域研究 (研究領域提案型)
研究期間 : 2015~2019
課題番号 : 15H05839
研究分野 : 有希合成化学
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