Syntheses and ion selectivities of tri-amide derivatives of hexahomotrioxacalix[3]arene. Remarkably large metal template effect on the ratio of cone vs. Partial-cone conformers

Hitoshi Matsumoto, Shoko Nishio, Michinori Takeshita, Seiji Shinkai

研究成果: Contribution to journalArticle査読

69 被引用数 (Scopus)

抄録

We have found that a homotrioxacalix[3]arene (1H3) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am3) between cone and partial-cone was sensitively affected in 0 ∼ 100% range by the metal template effects. Cone-1Am3 showed the very high affinity for alkali and alkaline earth metal cations. Particularly, it formed stable complexes with alkaline earth metal cations which were scarcely bound to the tri-ester derivative. The results show that cone-1Am3 acts as an excellent neutral ionophore owing to the three coordinative amide groups arranged in C3-symmetry.

本文言語英語
ページ(範囲)4647-4654
ページ数8
ジャーナルTetrahedron
51
16
DOI
出版ステータス出版済み - 4 17 1995
外部発表はい

All Science Journal Classification (ASJC) codes

  • 生化学
  • 創薬
  • 有機化学

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