Chromogenic reactions of steroids with strong acids. XI. Mechanism of chromogenic reaction otestosterone with sulfuric acid.

• 三浦 敏明

• 高木 英利

• 木村 道也

抄録

Mechanism was investigated for the chromogenic reaction of testosterone (I) with sulfuric acid. Dication (II in Chart 1) produced at the primary stage of the reaction was transformed into the chromophoric χ-484 (XIIa in Chart 4) via its conjugate base (VIII in Chart 4) by acid-base catalyzed isomerization. The conjugate base of the χ-484 (XIIb), 17, 17-dimethyl-18-norandrosta-4, 6, 8 (14)-trien-3-one (XIb), was isolated in 40% yield in the reaction of the epoxide (V in Chart 2) with sulfuric acid. Sulfuric acid solution of the trienone (XIa, b) showed a maximum absorption at 484 nm (ε=42000). The pK_a value of XIIa was also determined.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 27 (3), 783-788, 1979

  公益社団法人 日本薬学会

キーワード

• pK<SUB>a</SUB> of carbocation

詳細情報

• CRID: 1390282679150086912
• NII論文ID: 110003662248
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.27.783
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/27/3/27_3_783/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1980035681
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可