摘要
目的合成花椒毒素。方法连苯三酚为原料 ,经甲酯化、傅 克反应、氯甲基化得到 2 氯 2′ 羟基 3′ ,4′ 二甲氧基 5′ 氯甲基苯乙酮。再经环合、硼氢化钠还原得 6 ,7 二甲氧基 5 羟甲基苯并呋喃 ,然后用选择性氧化剂PCC将其结构上的伯醇羟基氧化为醛 ,三氯化铝脱甲基得 6 羟基 7 甲氧基 5 甲酰基苯并呋喃。最后经过Knoevenagel反应 ,脱羧 ,得到花椒毒素 ,并用1H NMR、MS以及IR验证产物结构。结果结构确证为花椒毒素 ,总收率约 9 0 % ,纯度 99%以上。结论该工艺路线合成花椒毒素是有效的、可行的 。
Aim To synthesize xanthotoxin in a simple way.Methods Xanthotoxin was synthesized from parogallol through nine steps with PCC used.The key compound in this synthesis is 2-chloro-2′-hydroxy-3′,4′-dimethoxy-5′-chloromethyl acetophenone,which was obtained from 2-chloro-2′-hydroxy-3′,4′-dimethoxyacetophenone through chloromethylation.Oxidation of 6,7-dimethoxy-5-hydromethylbenzofuran with the selective oxidant PCC yielded the 6,7-dimethoxy-5-formyl benzofuran.After Knoevenagel reaction of 6-hydroxy-7-methoxy-5-formyl benzofuran with malonic acid and decarboxylation,xanthotoxin is obtained.Its chemical structure was identified with ~1H-NMR,MS and IR.Results The structure was determined by spectrum.The overall yield was 9.0% and its purity was more than 99%.Conclusions Xanthotoxin can be synthesized in a practical way.The cost of the total synthesis is lower than the former one and the yield is definitely increased.
出处
《中国药物化学杂志》
CAS
CSCD
2004年第3期154-157,共4页
Chinese Journal of Medicinal Chemistry
关键词
药物化学
制备
化学合成
花椒毒素
medicinal chemistry
preparation
chemical synthesis
xanthotoxin
