Selective Epoxidation of β-Ionone Catalyzed by Iron-Doped Se/C

doi:10.6023/cjoc202205005

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3890-3895.DOI: 10.6023/cjoc202205005 Previous Articles Next Articles

NOTES

铁掺杂硒/碳催化β-紫罗兰酮的选择性环氧化

曹洪恩^a^,^b^,^*(), 李培梓^c^,^d, 景崤壁^d, 周宏伟^c^,^*()

^a扬州大学园艺与植物保护学院江苏扬州 225009
^b贵州大学绿色农药与农业生物工程教育部重点实验室贵阳 550025
^c嘉兴学院生物与化学工程学院浙江嘉兴 314001
^d扬州大学化学化工学院江苏扬州 225002

收稿日期:2022-05-04 修回日期:2022-06-26 发布日期:2022-07-13
通讯作者: 曹洪恩, 周宏伟
基金资助:
浙江省自然科学基金(LY19B020004); 贵州大学绿色农药与农业生物工程国家重点实验室培育基地/教育部重点实验室开放基金(2020GDGP0101); 嘉兴市动物模型创建与新药先导的精准合成重点实验室开放课题(jxsz21006); 江苏高校优势学科建设工程资助项目

Selective Epoxidation of β-Ionone Catalyzed by Iron-Doped Se/C

Hong'en Cao^a^,^b(), Peizi Li^c^,^d, Xiaobi Jing^d, Hongwei Zhou^c()

^aSchool of Horticulture and Plant Protection, Yangzhou University, Yangzhou, Jiangsu 225009
^bKey Laboratory of Green Pesticide and Agriculture Bioengineering of Ministry of Education, Guizhou University, Guiyang 550025
^cCollege of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001
^dSchool of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Received:2022-05-04 Revised:2022-06-26 Published:2022-07-13
Contact: Hong'en Cao, Hongwei Zhou
Supported by:
Natural Science Foundation of Zhejiang Province(LY19B020004); Open Fund of the State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering/Key Laboratory of Ministry of Education(2020GDGP0101); Open Project of Jiaxing Key Laboratory for Creation of Animal Models & Synthesis of Lead Compounds of New Drug(jxsz21006); Priority Academic Program Development of Jiangsu Higher Education Institutions

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Abstract

As an important intermediate in pharmaceutical synthesis, 5,6-epoxy-β-ionone has unique industrial application value. Recently, an iron-doped Se/C catalyst has been designed and prepared by calcining a mixture of methylselenized glucose with FeCl₃. The material could activate the molecular oxygen to achieve the selective epoxidation of β-ionone affording 5,6-epoxy-β-ionone. The catalyst is stable and recyclable, and the catalytic reaction process did not require any additive, so that the production cost could be obviously reduced. This cheap and safe catalytic oxidation technology using molecular oxygen as oxidant is of good industrial application values.

Key words: 5,6-epoxy-β-ionone, β-ionone, selenium, molecular oxygen, green catalysis

Cite this article

Hong'en Cao, Peizi Li, Xiaobi Jing, Hongwei Zhou. Selective Epoxidation of β-Ionone Catalyzed by Iron-Doped Se/C[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3890-3895.

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铁掺杂硒/碳催化β-紫罗兰酮的选择性环氧化

Selective Epoxidation of β-Ionone Catalyzed by Iron-Doped Se/C

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Entry	Solvent	Cat.	Oxidant	T/℃	t/h	Yield^b/%
1	1,4-Dioxane	Se/C-Fe	O₂	80	24	52
2	1,4-Dioxane	FeCl₃	O₂	80	24	46
3	1,4-Dioxane	FeCl₂	O₂	80	24	12
4	1,4-Dioxane	Fe₂O₃	O₂	80	24	17
5	DMF	Se/C-Fe	O₂	80	24	50
6	MeCN	Se/C-Fe	O₂	80	24	50
7	EtOAc	Se/C-Fe	O₂	80	24	45
8	EtOH	Se/C-Fe	O₂	80	24	21
9	THF	Se/C-Fe	O₂	80	24	18
10	1,4-Dioxane	Se/C-Fe	Air	80	24	19
11	1,4-Dioxane	Se/C-Fe	H₂O₂	80	24	23
12	1,4-Dioxane	Se/C-Fe	O₂	60	24	10
13	1,4-Dioxane	Se/C-Fe	O₂	100	24	57
14	1,4-Dioxane	Se/C-Fe	O₂	110^c	24	48
15	1,4-Dioxane	Se/C-Fe	O₂	100	12	42
16	1,4-Dioxane	Se/C-Fe	O₂	100	36	40

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