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化学学报
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化学学报 ›› 1955, Vol. 21 ›› Issue (2): 178-189. 上一篇    下一篇

论文

4-甲基-2-氧代-四氢化咪唑-5-脂酸的合成

张锦   

  1. 北京石油学院
  • 投稿日期:1955-03-16 发布日期:2013-06-04

SYNTHESIS OF 4-METHYL-2-IMIDAZOLIDONE-5-ALIPHATIC ACIDS

CHANG CHIN   

  1. Peking Petroleum Institute
  • Received:1955-03-16 Published:2013-06-04

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被引次数

2

(1)利用Friedel-Crafts反應,由4-甲基-2-氧代-二氫化咪唑及四個不同的醯氯羧酸酯,得到下列四個化合物:4-甲基-5-(δ-乙氧羰基-γ-甲基丁醯)-2-氧代-二氫化咪唑,4-甲基-5-(δ-乙氧羰基-γ,γ-二甲基丁醯)-2-氧代-二氫化咪唑,4-甲基-5-(ω-乙氧羰基-正壬醯)-2-氧代-二氫化咪唑及4-甲基-5-(ω-乙氧羰基-正十七醯)-2-氧代-二氫化咪唑。(2)用Cr2O3精製過的乙酸爲溶劑,PtO2爲觸媒,這四個4-甲基-2-氧代-二氫化咪唑的衍生物,很順利的吸收相當於3分子的氫,還原為相對應的4-甲基-2-氧代-四氫化咪唑的衍生物,水解後得到下列四個酸:4-甲基-5-(δ-羧基-γ-甲基丁基)-2-氧代-四氫化咪唑,4-甲基-5-(δ-羧基-γ,γ-二甲基丁基)-2-氧代-四氫化咪唑,4-甲基-5-(ω-羧基-正壬基)-2-氧代-四氫化咪唑及4-甲基-5-(ω-羧基-正十七基)-2-氧代-四氫化咪唑。前三者已作過初步的微生物效應試驗,對於lactobacilluscasei及saccharomycescerevisiae都有顯著的反促生素效應。第四個化合物因為在水中溶度太低,故尚未能作它的微生物效應試驗。

By means of Friedel-Crafts reaction, the following compounds were prepared from 4-methyl-imidazolone-2 and four different w-carbethoxy acyl halides: 4-methyl-5-(8-canbethoxy-y-methyl-butyryl)-imidazolone-2, 4-methyl-5-(8-carbethoxy-y, y-dimethylbutyryl)-imidazolone-2, 4-methyl-5-(ω-carbethoxy-n-nonanoyl)-imidazolone-2, and 4-methyl-5-(ω-canbethoxy-n-heptadecanoyl)-imidazolone-2. With PtO2 as catalyst, they were readily reduced to the four corresponding imidazolidone compounds. These compounds were hydrolyzed with 1 N NaOH and then followed by acidification to give the following acids: 4-methyl-5-(δ-carboxy-y-methylbutyl)-imidazolidone-2, 4-methyl-5-(δ-carboxy-y, y-dimethyl:butyl)-imidazolidone-2, 4-methyl-5-(ω-carboxy-n-nonanyl)-imidazolidone-2, and 4-methyl-5-(w}carboxy-n-heptadecanyl)-imidazolidone-2. Microbiological tests indicated that the first three acids are good anti-biotins towards lactobacillus casei and saccharomyces cerevisiae strain No, 139. Due to its extreme insolubility in water, the last compound has not yet been tested for its microbiological activity.