Chromogenic reactions of steroids with strong acids. VII. Reactions of A-aromatic steroids with concentrated sulfuric acid.

• 木村 道也

• 三浦 敏明

抄録

As in the case of 3-methoxy-17α-methylestra-1, 3, 5 (10)-trien-17β-ol (IV), the maximum absorption at 372 nm was immediately shown when 3-methoxyestra-1, 3, 5 (10)-trien-17α-ol (V), 3-methoxyestra-1, 3, 5 (10), 16-tetraene (VI), or 3-methoxy-17β-methyl-18-norestra-1, 3, 5 (10), 13-tetraene (VII) was dissolved in 97.2% H₂SO₄. Colorless leaflets, mp 122-124°, were obtained in 90% yield when IV came into contact with the same acid at room temperature for 20 min. Ultraviolet, mass and nuclear magnetic resonance spectral data indicated this product to be 3-methoxy-17, 17-dimethyl-13ξ, 14ξ-18-norestra-1, 3, 5 (10), 8-tetraene (VIIIb). Similarly, the same reaction of V, VI, or VII gave 3-methoxy-17β-methyl-13ξ, 14ξ-18-norestra-1, 3, 5 (10), 8-tetraene (VIIIa) in 80-90% yields, which also immediately shows maximum absorption at 372 nm in conc. H₂SO₄ (Chart 2). Formation of the stable carbocation III seemed to be slow in the case of estradiol-3-methyl ether (II). No χ-372 but χ-465 was formed in conc. H₂SO₄ with estrone methyl ether (I) which is in higher oxidation state than those of II, IV, V, VI, and VII (Fig. 1).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 24 (2), 181-185, 1976

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390282679149270016
• NII論文ID: 110003634980
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.24.181
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/24/2/24_2_181/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1976106704
• 本文言語コード: en
• データソース種別:
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• 抄録ライセンスフラグ: 使用不可