Page 200 - 《精细化工》2023年第6期

第 40 卷第 6 期 精 细 化 工 Vol.40, No.6
20 23 年 6 月 FINE CHEMICALS June 2023

香料与香精
两种新型羰基呋喃类香料前体的制备及其热性能

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李欣燕，张晓雨，赵巧玥，崔 冰，来洪涛，邵志晖 ，赵铭钦
（河南农业大学 烟草学院，河南 郑州 450002）

ipr
摘要：为开发羰基呋喃类香料前体，分别以 2-乙酰基吡啶、2-乙酰基噻吩和糠醇为起始原料，在 PNP 型 Pincer
锰催化剂的催化作用下经脱氢偶联反应一步合成 3-(呋喃-2-基)-1-(吡啶-2-基)丙-1-酮（Ⅲa）和 3-(呋喃-2-基)-1-(噻
1
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吩-2-基)丙-1-酮（Ⅲb）。通过 HNMR、 CNMR、HRMS 表征目标化合物的结构，并对其热性能进行测试。结
果表明，化合物Ⅲa 从 99.9 ℃开始降解，主要失重区间为 99.9~875.0 ℃，在 256.0 ℃失重速率最大，总失重率
为 97.31%；化合物Ⅲb 从 116.2 ℃开始降解，主要失重区间为 116.2~875.0 ℃，在 269.0 ℃失重速率最大，总
失重率为 98.42%。在 300~900 ℃有氧裂解氛围下，化合物Ⅲa 裂解后主要有烯基呋喃、烷基吡啶、2-乙酰基吡
啶等特征香味物质；化合物Ⅲb 裂解后鉴定出 2-丙基呋喃、噻吩及其衍生物、烯基呋喃等特征香味物质。通过
对单料烟进行加香效应评价，确定化合物Ⅲb 的最适宜添加量为 3 mg/kg。
关键词：羰基呋喃类香料前体；糠醇；3-(呋喃-2-基)-1-(吡啶-2-基)丙-1-酮；3-(呋喃-2-基)-1-(噻吩-2-基)丙-1-酮；
热性能；热裂解；加香效应；香料与香精
中图分类号：TS264.3；O622.4 文献标识码：A 文章编号：1003-5214 (2023) 06-1350-06

Preparation and thermal properties of two novel carbonyl
furan spice precursors

LI Xinyan, ZHANG Xiaoyu, ZHAO Qiaoyue, CUI Bing, LAI Hongtao,
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SHAO Zhihui , ZHAO Mingqin
（College of Tobacco Science, Henan Agricultural University, Zhengzhou 450002, Henan, China）
Abstract: In order to develop carbonyl furan spice precursors, 3-(furan-2-yl)-1-(pyridin-2-yl)propan-1-one
(Ⅲa) and 3-(furan-2-yl)-1-(thiophen-2-yl)propan-1-one (Ⅲb) were synthesized, under the catalysis of
ipr
PNP pincer manganese, respectively via one step dehydrogenative coupling reaction of 2-acetylpyridine,
1
2-acetylthiophene and furfuryl alcohol. The compounds obtained were then characterized by HNMR,
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CNMR and HRMS, followed by analysis on their thermal properties. The results showed that compound
Ⅲa started degrading at 99.9 ℃ with the main weight loss interval ranging at 99.9~875.0 ℃, and reached
the maximum weight loss rate at 256.0 ℃ with a total weight loss rate of 97.31%, while compound Ⅲb
began to degrade at 116.2 ℃ with the main weight loss interval of 116.2~875.0 ℃, and reached the
maximum weight loss rate at 269.0 ℃ with a total weight loss rate of 98.42%. The aerobic cracking
products of compound Ⅲa from 300~900 ℃ were mainly composed of alkenyl furans, alkyl pyridines,
2-acetylpyridine and other characteristic fragrance substances, while those of compound Ⅲb mainly
included 2-propylfuran, thiophene and its derivatives, alkenyl furans as well as other characteristic fragrance
substances. Based on the evaluation of incense effect, the most suitable amount of compound Ⅲb added in a
single cigarette was 3 mg/kg.
Key words: carbonyl furan spice precursors; furfuryl alcohol; 3-(furan-2-yl)-1-(pyridin-2-yl)propan-1-one;
3-(furan-2-yl)-1-(thiophen-2-yl)propan-1-one; thermal properties; thermal cracking; incense effect;
perfumes and essences

收稿日期：2022-08-24; 定用日期：2022-12-01; DOI: 10.13550/j.jxhg.20220788
基金项目：河南省科技厅重点科技攻关项目（30600715）；河南农业大学校内基金（30501028）
作者简介：李欣燕（1998—），女，硕士生，E-mail：lixinyan1618@163.com。联系人：邵志晖（1991—），男，讲师，E-mail：
shaozh21@henau.edu.cn；赵铭钦（1964—），男，教授，E-mail：zhaomingqin@126.com。