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甲基、异甲基紫罗兰酮的合成及其立体化学
SYNTHESES AND STEREOCHEMISTRY OF ISOMERIC METHYLIONONES
【摘要】 用正交试验和方差分析方法研究了柠檬醛与丁酮的醇醛缩合反应。以97%柠檬醛为原料,氢氧化钾一甲醇溶液为缩合剂,室温反应6小时,得率88~89%,其中异甲基假性紫罗兰酮64~66%。缩合产物经GLC和NMR分析证明柠檬醛与丁酮缩合时,柠檬醛分子中的立体构型未发生改变。通过~1HNMR谱的NOE分析及芳香溶剂的诱导效应,确定了甲基、异甲基假性紫罗兰酮的四种异构体及它们的环化产物:α-甲基、β-甲基及α-异甲基、β-异甲基紫罗兰酮的立体构型。
【Abstract】 The aldol condensation of citral with butanone has been invesigated. Latin square esign and analysis of varianoe were used. Reaotion prooeeded for six hours at room temperature sing methanolio KOH solution as condensation agent and 97% oitral as starting material, and he ield was 88~89%, in whioh 64~66% were isomethylpseudoionone. The condensation products were nalysed by GLC and NMR spectra and it was proved that during the condensation of oitral with utanone, the configuration of the C=C double bond of citral was not changed.By ~1H NMR spectra nd the application of NOE and induction effect of aromatio solvent, the stereochemistry of our somers from aldol condensation of oitral with butanone, methylpseudo-and isomethylpseudo-onones and their corresponding oyolization products, i. e. α-methyl-and α-isomethyl-ionones and heir β-isomors were determined.
- 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1981年Z1期
- 【被引频次】6
- 【下载频次】219