(1S,3R,5S,6R)-6-ヒドロキシ-8-メチル-8-アザビシクロ[3.2.1]オクタン-3-イル 3-メチルブタノアート

(1S,3R,5S,6R)-6-ヒドロキシ-8-メチル-8-アザビシクロ[3.2.1]オクタン-3-イル 3-メチルブタノアート 化学特性,用途語,生産方法

• 説明

  An alkaloid found in Duboisia myoporoides, the base crystallizes from EtOH in colourless, nacreous plates and has [α]²⁰_D - 9.0° (c 5.0, EtOH), or - 4.0° (c 5.0, H2O). It yields a crystalline hydrobromide as colourless needles, m.p. l70-2°C; [α]²⁰_D + 5.0° (c 20.0, H20); picrate, m.p. lS2-3°C; methiodide, m.p. 20S.SoC and the acetyl derivative, characterized as the hydrobromide, m.p. 197°C. The isovaleryl ester forms a hydrochloride, m.p. l24-SoC; [α]_D + 2.6° (c 3.78, EtOH) and a hydrobromide, m.p. l76-7°C. Treatment of the hydrobromide with thionyl chloride gives norvaleroidine due to demethylation, a colourless syrup which furnishes a crystalline hydrobromide, m.p. 270°C; [α]²⁰_D + 1 ° (c 20.0, H20). On hydrolysis with aqueous Ba(OHh, the base gives dihydroxytropane and isovaleric acid while oxidation with KMn04 furnishes norvalieroidine and a base C13H190 4N, m.p. 136°C; [α]²⁰_D - 16.6° (c 7.4, EtOH).

• 参考文献

  Barger, Martin, Mitchell.,!. Chem. Soc., 1820 (1937)
  Barger, Martin, Mitchell., ibid, 1685 (1938)
  Martin, Mitchell., ibid, 1155 (I 940)
  Mitchell, Troutner., ibid, 1330 (I 947)
  Fodor, Kovacs., ibid, 2341 (1953)
  Fodor, Vincze, Toth., ibid, 1349 (1957)
  Fodor, Vincze, Toth., ibid, 3219 (1961)

(1S,3R,5S,6R)-6-ヒドロキシ-8-メチル-8-アザビシクロ[3.2.1]オクタン-3-イル 3-メチルブタノアート 生産企業

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