Abstract: Six pinonic acid esters were synthesized from one-pot ozonolysis reaction using α-pinene and alcohol as raw materials, dichloromethane as solvent, and decomposition of the prepared ozonide by acetic anhydride (AA) with triethylamine (TEA) as catalyst. The influences of acetic anhydride quantity, triethylamine quantity, reaction time and reaction temperature were investigated. The synthesis conditions were optimized by orthogonal experiment. The optimized conditions were as follows：nAA/nα-pinene = 3.0∶1, nTEA/nα-pinene = 0.75∶1, time and temperature 60 min and 30 ℃ respectively. The yields of six pinonic acid esters were above 60%. The structures of the six pinonic acid esters were identified and characterized by IR, 1H NMR, 13C NMR and MS. This method was a convenient and efficient way to synthesize pinonic acid esters, which had such advantages as simple operation, mild conditions and high yields.

Key words: α-pinene, triethylamine, acetic anhydride, ozonide, pinonic acid esters

摘要： 以天然产物松节油的主要成分α-蒎烯和醇为原料，二氯甲烷为溶剂，经臭氧氧化制得α-蒎烯臭氧化物，臭氧化物不加分离直接在三乙胺（TEA）催化下经乙酸酐重排（AA）裂解，一锅法合成了6种蒎酮酸酯类化合物。考察了乙酸酐用量、三乙胺用量、反应时间和反应温度等条件对蒎酮酸酯收率的影响，并通过正交试验对合成条件进行了优化。优化的实验条件为：nAA/nα-蒎烯 = 3.0∶1，nTEA/nα-蒎烯 = 0.75∶1，反应时间为60 min，反应温度为30 ℃，在该条件下合成的6种蒎酮酸酯收率均在60%以上，并采用1H NMR、13C NMR、IR、MS对6种化合物的结构进行了表征。该方法操作简便，条件温和，且收率高，是合成蒎酮酸酯类化合物的一种简易可行的方法。

关键词: α-蒎烯, 三乙胺, 乙酸酐, 臭氧化物, 蒎酮酸酯