烟草科技Issue(6)：45-51,7.DOI:10.16135/j.issn1002-0861.20150609
甲基环戊烯醇酮-β-D-吡喃葡糖苷的合成及其热裂解
Synthesis and Pyrolysis of Methylcyclopentenolone-β-D-glucopyranoside
摘要
Abstract
Taking D-glucose as material, 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide(Compound 2) and 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (Compound 4′) were synthesized byα-D-acetobromoglucose method (Method A) and trichloroacetonitrile method (Method B), respectively. Compounds 2 and 4′ were coupled with methylcyclopentenolone(MCP), then deacetylated to form MCP-β-D-glucopyranosides [3-methyl-1-oxocyclopenta-2-en-2-yl-β-D-glucopyranoside (Compound 1) and 5-methyl-1-oxocyclopenta-2-en-2-yl-β-D-glucopyranoside (Compound 1′), respectively. The molecular structures of intermediates and final products were characterized by 1H NMR and HRMS. The thermal pyrolysis of glucosides 1 and 1′ was also studied, and the results indicated that: 1) The compounds synthesized by the two methods were target products, Method A was better than Method B. 2)The optimal conditions of Method A were the molar ratio of MCP to compound 2 1∶1.2 and reacting at 35 ℃ for 5 hours, the yield of target product reached 82.0% and the total yield of reaction was 59.6%. 3)Glucosides 1 and 1′were added into cigarettes separately, the glucosides pyrolyzed into MCP during smoking, and their <br> transfer rates to mainstream cigarette smoke were 16.13% and 16.40%, respectively.关键词
吡喃葡糖苷/甲基环戊烯醇酮/合成/热裂解/卷烟烟气Key words
Glucopyranoside/Methylcyclopentenolone/Synthesis/Pyrolysis/Cigarette smoke分类
化学化工引用本文复制引用
李有桂,卢梦梦,朱成峰,徐迎波,陈开波..甲基环戊烯醇酮-β-D-吡喃葡糖苷的合成及其热裂解[J].烟草科技,2015,(6):45-51,7.基金项目
烟草化学安徽省重点实验室开放课题“焦甜香潜香物质--环戊烯醇酮类糖苷的合成及在卷烟中的应用研究” （）
