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一種八氫香豆素衍生物的合成及香氣研究

Synthesis and Aroma Evaluation of A Octahydro Coumarin Derivative

  • 摘要: 利用異佛爾酮為起始原料合成了一種消旋八氫香豆素衍生物,並初步評估了它的香氣特征。認為它作為一種稠環內酯化合物具有用於日化香精的調配的潛在可能。以鈀/碳為催化劑,異佛爾酮經選擇性催化氫化得到二氫異佛爾酮⛹🏻‍♂️;二氫異佛爾酮的烯胺與丙烯酸甲酯發生邁克爾加成反應得到的3-(2😭,4,4-三甲基-6-氧代-環己基)丙酸甲酯,再經堿性條件下水解🔙👸🏿,硼氫化鉀還原得到δ-羥基羧酸,最後δ-羥基羧酸經酸催化發生分子內酯化反應生成一種消旋八氫香豆素衍生物5,7🧚,7-三甲基-八氫-2H-苯並吡喃-2-酮👷‍♂️。目標化合物通過紅外光譜→、核磁共振氫譜🧚🏽、碳譜以及質譜進行了表征🔪。

     

    Abstract: A new racemic octahydrocoumarin derivative was synthesized from isophorone and its aroma characteristics were evaluated preliminarily. As a kind of fused-ring lactone compound, It could be used for the daily fragrances. Using palladium on carbon as catalyst, isophorone was reduced selectively to obtain dihydroisophorone; Methyl 3-(2,4,4-trimethyl-6-oxo-cyclohexyl)propanoate was obtained by Michael addition reaction of enamine of dihydroisophorone with methyl acrylate. It was then hydrolyzed under basic conditions, reduced with potassium borohydride to obtain δ-hydroxycarboxylic acid, and finally acid-catalyzed Intramolecular esterification of δ-hydroxy carboxylic acid to form a racemic octahydrocoumarin derivative, 5,7,7-trimethyl-octahydro-2H-benzopyran-2-one; The target compound were characterized by IR, 1H NMR, 13C NMR and MS.

     

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