β-蒎烯合成四元环类化合物的研究

Studies on the Synthesis of Four-ring Compounds from β-pinene

用压热法由β-蒎烯与多聚甲醛合成了诺卜醇,再由诺卜醇合成了诺卜乙基醚,并用MS,IR,1HNMR及13CNMR对诺卜乙基醚的结构进行了表征。通过GC-MS分析确定了6个诺卜醇臭氧化主要产物的结构,它们均为四元环类化合物,这表明诺卜醇臭氧化时碳碳双键、叔氢都会被氧化,还伴有其它更深层次的反应。对诺卜乙基醚的碱性KMnO4氧化反应产物进行了GC-MS分析,确定了4个主要产物的结构,它们均为四元环类化合物,这表明反应首先生成2,3-二醇,然后继续氧化断裂得到环丁烷乙酸,或者脱水后得到2,3-环氧化合物。

Nopol was synthesized by autoclaving paraformaldehyde and b-pinene, then nopyl ethyl ether was synthesized from nopol, and the structure of nopyl ethyl ether was identified by MS, IR,~1H MNR and ^(13)C NMR. The structures of 6 main products of ozonization of nopol were identified by GC-MS, and they are all four-ring compounds, the result suggests that the double bond, tertiary hydrogen can be oxidized, and there was other further oxidation. The structures of 4 main products of oxidation of nopyl ethyl ether with basic KMnO_4 were identified by GC-MS, and they are all four-ring compounds, the result suggests that the first product is 2,3-diol, and then can be further cleaved to produce acetic acid of cyclobutane or dehydrated to produce 2,3-epoxide.