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]
20D - 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)
リコポジン 上流と下流の製品情報
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