リコポジン

リコポジン 化学特性,用途語,生産方法

• 解説

  15(R)-methyllycopodan-5-one．C16H25NO(247.38)．リコポジン, ヒカゲノカズラ科Lycopodium clavatumをはじめ，種々の同属の植物から分離された100種類近いリコポジウムアルカロイドの代表的なもの．構造上はキノリジジンアルカロイドに属する．植物内でリシンより生合成される．融点114～115 ℃．[α]_D－24°(エタノール)．水，有機溶媒に可溶．森北出版「化学辞典（第2版）

• 説明

  This alkaloid has, so far, been discovered in all Lycopodium species with the exception of L. saururus Lam. It was first obtained by B6deker who assigned to it the formula C32Hs203N2, altered to that given by Achmatowicz and Uzieblo and confirmed by Manske and Marion. It forms colourless prisms from Et20 and has [α]²⁰_D - 9.01 ° (Me2CO). It yields crystalline salts and derivatives: the perchlorate, m.p. 276°C; methochloride, m.p. 238-240°C, methiodide, m.p. 335- 7°C and a hydrazone, mop. 20B-2l0°C. According to Bodeker it also yields a crystalline hydrochloride and aurichloride.
  Even under pressure at 200°C in the presence of Raney Ni, the base cannot be hydrogenated. On selenium dehydrogenation, a complex mixture of bases is formed from which 7 -methylquinoline and 5:7 -dimethylquinoline have been identified. 7 -methylquinoline is also stated to be formed when the base is heated with palladium as catalyst. A stereospecific total synthesis of the (±)-form has been described.

• 参考文献

  Bodeker., Annalen., 208,363 (1881)
  Achmatowicz, Uzieblo., Rocz. Chern., 18,89 (1938)
  Manske, Marion., Can. 1. Res., 20B, 87 (1942)
  Marion, Manske., ibid, 20B, 153 (1942)
  Manske, Marion., 1. Arner. Chern. Soc., 69,2126 (1947)
  Anet., Tetrahedron Lett., 20, 13 (1960)
  Harrison et al., Can. 1. Chern., 39,2086 (1961)

• 参考文献

  M.U. Haque, D. Rogers, J. Chem. Soc., Perkin Trans. 2, 1975, 93, DOI: 10.1039/P29750000093.

リコポジン 生産企業

Global(9)Suppliers