Page 53 - 《精细化工》2020年第8期

第 8 期 曹海泳，等: 二烯酮类化合物在构建复杂有机化合物中的应用
SGLT-2 抑制剂类 2 型糖尿病治疗药物，通过抑制肾
脏对葡萄糖的重吸收及诱导血液中过多的葡萄糖排
泄进入尿液而发挥降糖作用。据估计，该药有望成
为一种新兴的口服降糖药。该药物的关键中间体可
由分子内具有二烯酮和炔结构单元的化合物（33）
经分子内[4+2]环加成/氧化反应来实现
现，化合物（33）在乙腈中加热至 80 ℃即可发生[4+2]
环加成反应，随后在空气中迅速氧化为产物 34，但
是得到的为 34a 和 34b 两个异构体的混合物，然而
在三氟化硼作用下，副产物 34b 可高效异构化为
34a，最后经还原、脱保护得到目标产物托格列净（35）。
4 结束语与展望
国内外多个课题组分别以 2,5-环己烯酮类、1,4-
戊二烯-3-酮类和 2,4-戊二烯-1-酮类等二烯酮类化合
物 为反应底 物，与多 种不同试 剂发生串 联
Michael-Smiles 环丙烷化、串联 1, 6-共轭加成/环加
成、三组分 Ritter 反应、交叉偶联反应、双 Michael
加成、1,3-偶极环加成反应、分子内 MBH 反应、分
子内还原 Aldol 反应、分子内 Aldol 反应等，构建了
多种类型的具有不同功能的化合物，如环丙烷类衍
生物、酰胺类化合物、不对称联芳烃类化合物、多
取代环己酮类化合物、噻喃酮类化合物、螺环氧化
吲哚类化合物、螺环吡唑啉类化合物、多取代茚酮
类化合物等。尤其是中国化学工作者在这些领域积
极地开展了研究工作，部分研究成果属首次报道。
不难发现，虽然有关二烯酮的研究取得了突破性的
进展，但还有很多工作需要去研究和探索：（1）寻
找适合催化二烯酮反应体系的催化剂，开发高效、
高选择性的催化体系；（2）设计合成结构新颖的反
应底物，进一步丰富二烯酮反应类型的多样性；
（3）深入探索所合成的目标产物在医药、农药、材
·1551·
料科学等领域的应用。这些研究工作将进一步丰富
二烯酮化学反应的多样性，为具有潜在生物和药物
活性化合物的合成提供物质基础。
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