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谭晓, 郑湘婷, 康宁, 刘韵竹, 欧阳震申, 赵野町, 傅榕赓.单质硫催化查尔酮类化合物选择性还原制备二氢查尔酮的研究[J].湖南中医药大学学报英文版,2025,45(4):662-667.[Click to copy
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| 单质硫催化查尔酮类化合物选择性还原制备二氢查尔酮的研究 |
| 谭晓,郑湘婷,康宁,刘韵竹,欧阳震申,赵野町,傅榕赓 |
| (湖南中医药大学药学院, 湖南 长沙 410208) |
| 摘要: |
| 目的 探讨在单质硫催化下利用水作氢源选择性还原查尔酮类化合物制备二氢查尔酮类化合物的合成方法。方法 以查尔酮作为模型探究最佳反应条件，并考察不同类型取代基对反应产率的影响。结果 反应最佳条件为0.5 mmol查尔酮、1.25倍量单质硫、2.5倍量1,4-二氮杂二环[2.2.2]辛烷、400 μL水以及2.5 mL N,N-二甲基甲酰胺，N2保护下120 ℃反应12 h。在底物范围扩展中有效得到一系列二氢查尔酮化合物，经1H NMR、13C NMR以及HR-ESI-MS确证其结构。结论 单质硫/水/1,4-二氮杂二环[2.2.2]辛烷/N,N-二甲基甲酰胺体系可以选择性还原查尔酮制备二氢查尔酮，该方法具有底物适用范围广，绿色环保、操作简单、产率优良的特点。 |
| 关键词: 单质硫 查尔酮 二氢查尔酮 选择性还原 合成 |
| DOI：10.3969/j.issn.1674-070X.2025.04.011 |
| Received:February 11, 2025 |
| 基金项目:湖南省自然科学基金项目（2025JJ80138）；湖南中医药大学生创新创业训练计划项目。 |
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| Elemental sulfur-catalyzed selective reduction of chalcones to dihydrochalcones |
| TAN Xiao, ZHENG Xiangting, KANG Ning, LIU Yunzhu, OUYANG Zhenshen, ZHAO Yeting, FU Ronggeng |
| (School of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan 410208, China) |
| Abstract: |
| Objective To investigate the synthetic method for preparing dihydrochalcones by selectively reducing chalcones using water as the hydrogen source under the catalysis of elemental sulfur. Methods Chalcone was used as a model substrate to investigate the optimal reaction conditions, and the influence of different types of substituents on the reaction yield was examined. Results The optimal reaction conditions were as follows: 0.5 mmol of chalcone, 1.25 equivalents of elemental sulfur, 2.5 equivalents of 1,4-diazabicyclo[2.2.2]octane, 400 μL of water, and 2.5 mL of N,N-dimethylformamide, with the reaction conducted at 120 °C for 12 h under N2 protection. A series of dihydrochalcones were effectively obtained in the expansion of the substrate scope, and their structures were confirmed by 1H-NMR, 13C-NMR, and HR-ESI-MS. Conclusion The system of elemental sulfur/water/1, 4-diazabicyclo[2.2.2]octane/N, N-dimethylformamide can selectively reduce chalcone to dihydrochalcone. This method features a wide range of applicable substrates, environmental friendliness, simple operation, and excellent yield. |
| Key words: elemental sulfur chalcone dihydrochalcone selective reduction synthesis |
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