GC-MS分析确认乙酸诺卜酯氧化反应产物的结构

Structural Identification of the Products of Nopyl Acetate Oxidation by GC-MS

三氧化铬酸性水溶液氧化乙酸诺卜酯反应中的主要产物是4-(1-甲基-1-羟基乙基)-1-环己烯-1-乙醇乙酸酯和4-(1-甲基-1-羟基乙基)-1-环己烯-1-乙醇,通过GC-MS分析确定了反应产物中其他几个GC含量相对较高的组分,主要是3组异构体:2,3-环氧乙酸诺卜酯、1-羟基-2,3-环氧乙酸诺卜酯和5-羟基-2,3-环氧乙酸诺卜酯.分析结果表明反应主要是四元环开裂,并进一步水合,另外伴有少量双键环氧化的产物,这些环氧化的产物还可进一步在C1和C5处发生叔氢氧化.

Nopyl acetate was oxidized by acidic aqueous chromic anhydride, the main products were 4-（ 1-methyl-l-hy- droxy-ethyl） - 1-cyclohex-ene- 1-ethanolacetate and 4- （ 1 -methyl- 1 -hydroxyethyl） - 1 -cyclohexene- 1 - ethanol. Several other products, which have comparatively high GC content, mainly include 3 couple of isomers, have been identified by GC- MS. They are 2,3-epoxynopyl acetate, 1-hydroxy-2,3-epoxynopyl acetate and 5-hydroxy-2, 3- epoxynopyl acetate. The results suggested that the four-ring of nopyl acetate cleaved firstly in the reaction, and then hydrated. The other products mainly obtained from epoxidation of the double bond, and further oxidation of tertiary hydrogen on C1 and C5.