Determination of Ring Conformation in 1-Benzyl-1,2,3,4-tetrahydroisoquinolines and a New Synthesis of the Chiral Compounds.

• SHINOHARA Tatsumi

• TAKEDA Akira

• TODA Jun

• SANO Takehiro

書誌事項

タイトル別名

• Determination of Ring Conformation in 1

抄録

The conformation of the piperideine ring in 1-benzyl-1, 2, 3, 4-tetrahydroisoquinolines was determined as ²H₃ form with a pseudoaxial position of the 1-benzyl group by circular dichroism (CD) spectral comparison with 1-methyl-1, 2, 3, 4-tetrahydroisoquinolines. The chiral center at C-1 of 1, 2, 3, 4-tetrahydroisoquinoline (TIQ) was constructed in an unambiguous manner by applying a new method of TIQ synthesis utilizing the Pummerer reaction as a key step. Enantiomerically pure (R)- and (S)-1-methyl- and 1-benzyltetrahydroisoquinolines (1) were prepared starting from readily available chiral amines (2) in good overall yields.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 46 (3), 430-433, 1998

  公益社団法人 日本薬学会

キーワード

• 1-benzyl-1, 2, 3, 4-tetrahydroisoquinoline
• conformation
• circular dichroism spectrum
• Pummerer reaction
• 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline

詳細情報

• CRID: 1390001204158150016
• NII論文ID: 130003773762
• NII論文ID: 110003616884
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.46.430
• COI: 1:CAS:528:DC%2BD3MXls1Omtb8%3D
• ISSN: 13475223
• ISSN: 00092363
• ISSN: http://id.crossref.org/issn/00092363
• NDL書誌ID: 4440417
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4440417
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/46/3/46_3_430/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可