Functionalized Oxatriquinanes and Their Structural Equilibrium in Protic Solvent

• Suzuki Hideyuki

  Research Foundation Itsuu Laboratory

• Muratake Hideaki

  Research Foundation Itsuu Laboratory

抄録

We synthesized oxatriquinane hexafluorophosphate bearing an ethoxycarbonylmethyl group 7 or a 2-oxopropyl group 11. Both of these organic oxonium cation compounds were obtained as stable solids. However, ¹H-NMR analysis showed that oxatriquinane 7 was present as the oxonium cation in aprotic solvent CD₃CN, but was in rapid equilibrium with ring-opened bicyclic compound 8 in protic solvent CD₃OD. The oxatriquinane 11 also showed similar behavior in protic solvent. Phenyl-substituted oxatriquinanes 12 and 14 were also obtained as stable solids, and showed similar properties to 7 and 11.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 62 (9), 921-926, 2014

  公益社団法人 日本薬学会

キーワード

• oxatriquinane
• organic oxonium cation
• equilibrium
• protic solvent

詳細情報

• CRID: 1390282679155642880
• NII論文ID: 130004053813
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c14-00384
• COI: 1:STN:280:DC%2BC2cbgvFKquw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 025737015
• PubMed: 25007813
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I025737015
• Web Site: https://www.jstage.jst.go.jp/article/cpb/62/9/62_c14-00384/_pdf
• 本文言語コード: en
• データソース種別:
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  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可