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金微素的化学I.金微素及其衍化物的氢解和芳构化

STUDIES ON THE CHEMISTRY OF AUREOMYCIN I. HYDROGENOLYSIS AND AROMATIZATION OF AUREOMYCIN AND ITS DERIVATIVES

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【作者】 黄耀曾丁宏勋丁维钰盛怀禹涂通源黄敬坚徐元耀汪猷

【Author】 HUANG YAO-TSENG(YAO-TSENG HUANG),TING HUNG-SHIUN(HUNG-SHIUN TINC),TING WEI-YI,SHENG HAI-YU,TU TUNG-YUAN,HUANG JING-JAIN,HSU YUEN-YAOand WANG YU(YU WANG)Institute of Organic Chemistry,Academia Smica

【机构】 中国科学院有机化学研究所中国科学院有机化学研究所

【摘要】 金黴素(I)在冰醋酸與甲醇溶液中,用鋅粉氫解,在温和條件下,產生脫二甲胺金黴素(II);較劇烈條件下,則生成脫二甲胺脫羥金黴素(III)。III從II經鋅粉醋酸氫解得到。 I,II,III分別與濃鹽酸或甲醇鹽酸處理相應地得到脫水金黴素(IV),脫二甲胺脫水金黴素(V)及脫二甲胺脫羥脫水金黴素(VI)。脫水金黴素(IV)經鋅粉醋酸氫解亦產生V與VI。VI亦可從V製成。 I,II,III,IV,V或VI和鋅粉共同蒸餾,皆得到并四苯。 從紫外吸收光譜測定,對金黴素結構中二甲胺基及角羥基的位置有補充的說明。

【Abstract】 Aureomycin (Ⅰ) on reduction with zinc-acetic acid gives desdimethylaminoaureomycin (Ⅱ) under mild conditions and desdimethylaminodesoxyaureomycin (Ⅲ) under more drastic conditions. Ⅱ can be converted into Ⅲ by further reduction. Treatment of Ⅰ, Ⅱ or Ⅲ with concentrated hydrochloric acid or methanolic HCl produces anhydroaureomycin (Ⅳ), desdimethylaminoanhydroaureomycin (Ⅴ) or desdimethylaminodes- oxyanhydroaureomycin (Ⅵ) respectively. Compound (Ⅴ) can be obtained from Ⅳ by hydrogenolysis, and, similarly, Ⅵ from either IV or V. All the above compounds, (Ⅰ), (Ⅱ), (Ⅲ), (Ⅳ), (Ⅴ) and (Ⅵ), when subjected to zinc dust distillation, form naphthacene. A comparison of the ultra-violet absorption spectra of Ⅰ, Ⅱ, Ⅲ, Ⅳ, Ⅴ and Ⅵ affords a supplementary evidence for the location of the angular-OH group in the structure of aureomycin.

  • 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1955年02期
  • 【被引频次】3
  • 【下载频次】26
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