茶螺烷酮合成的新工艺

A New Synthetic Approach to Theaspirone

以α-紫罗兰酮为原料,经间氯过氧苯甲酸环氧化、甲醇钠开环、超声波辐射Pd/C催化甲酸铵选择性碳碳双键加H、硼氢化钠还原、脱水环化及乙酰丙酮亚钴催化烯丙位氧气氧化等6步反应,以总收率52.6%合成了食用香料2,6,10,10-四甲基-1-氧杂-螺[4.5]-6-癸烯-8-酮(茶螺烷酮)。用IR、1HNMR、MS谱及元素分析等测试技术表征了产物的结构和组成。

An edible perfume theaspirone,1-oxa-8-oxo-2,6,10,10-tetramethyl-spiro-[4,5]-6-decene,was synthesized from α-ionone with 52.6% overall yield via six steps including epoxiation by metachloroperbenzoic acid,ring-opening in the presence of sodium methoxide,selective reduction of carbon-carbon double bond catalyzed by Pd/C with ammoniumformate under ultrasonic irridiation,then reduction with sodium borohydride,intramolecular cyclodehydration and allylic oxidation catalyzed by acetylacetone cobalt（Ⅱ） with oxygen gas.The structures and compositions of the product and some intermediates were characterized by IR,1 H NMR,MS and elemental analysis.