AMINE OXIDES .1. GRAMINE OXIDE
AMINE OXIDES .1. GRAMINE OXIDE
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DOI：
10.1021/ja01576a051
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发表时间：
1957-01-01
影响因子：
15
通讯作者：
LEETE, E
中科院分区：
文献类型：
--
作者：
HENRY, DW;LEETE, E
Treatment of gramine with hydrogen peroxide yields gramine oxide (I). On heating, gramine oxide rearranges to O-skatyl-N, N-dimethylhydroxylamine (II). Nucleophilic reagents (amines, alkoxides, hydroxide, cyanide and the nitromethyl anion) react with gramine oxide yielding the corresponding skatyl derivatives and N, N-dimethylhydroxylamine. Gramine oxidedecomposes in water at 100 yielding 3, 3'-diindolylmethane, formaldehyde and polymeric material. Acids decompose the oxide yielding amorphous material and N, N-dimethylhydroxylamine.Gramine(3-dimethylaminomethylindole) is found in the leaves ofgerminating barley, but one month after germination all the gramine has disappeared from the plant. 3 We considered that gramine oxide (I) would be a plausible metabolite of gramine. This communication is an account of the synthesis and properties of gramine oxide. Aliphatic amine oxides are usually hygroscopic oils4· 6; however, we found that the treatment of gramine in ethanol solution with hydrogen peroxide yielded non-hygroscopic crystals of gramine oxide which crystallized with one mole of hydrogen perox-ide. 6 When the excess hydrogen peroxide was decomposed after oxidation of gramine, the gramine oxide did not crystallize out and removal of the ethanol in vacuo yielded a viscous oil readily soluble in water.
