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2022 , Vol. 42 >Issue 11: 3890 - 3895

DOI: https://doi.org/10.6023/cjoc202205005

研究简报

铁掺杂硒/碳催化β-紫罗兰酮的选择性环氧化

  • 曹洪恩 ,
  • 李培梓 ,
  • 景崤壁 ,
  • 周宏伟
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  • 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

  网络出版日期: 2022-07-14

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

收起

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

  • Hong'en Cao ,
  • Peizi Li ,
  • Xiaobi Jing ,
  • Hongwei Zhou
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  • 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
*E-mail: ;

Received date: 2022-05-04

  Revised date: 2022-06-26

  Online published: 2022-07-14

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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摘要

5,6-环氧-β-紫罗兰酮作为药物合成中的重要中间体, 具有独特的工业应用价值. 最近, 我们将甲硒化葡萄糖和氯化铁混合煅烧, 设计制备了一种铁掺杂的硒/碳催化剂. 该材料可活化分子氧, 从而选择性氧化β-紫罗兰酮, 合成得到5,6-环氧-β-紫罗兰酮. 该催化剂性能稳定, 可循环套用, 且催化反应过程无需额外添加助催化剂, 从而显著降低了生产成本. 这一利用分子氧为氧化剂的廉价、安全的催化氧化技术有很好的工业应用价值.

关键词： 5,6-环氧-β-紫罗兰酮; β-紫罗兰酮; 硒; 分子氧; 绿色催化

本文引用格式

曹洪恩 , 李培梓 , 景崤壁 , 周宏伟 . 铁掺杂硒/碳催化β-紫罗兰酮的选择性环氧化[J]. 有机化学, 2022 , 42(11) : 3890 -3895 . DOI: 10.6023/cjoc202205005

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

参考文献

[1]
Ansari, M.; Emami, S. Eur. J. Med. Chem. 2016, 123: 141.
[2]
(a) Peng, Z.; Lu, G. Catal. Lett. 2007, 117, 126.
[2]
(b) Li, H.; Cao, H.; Chen, T.; Zhang, X.; Shi, Y. Mol. Catal. 2019, 483, 110715.
[2]
(c) Yang, Y.; Fan, X.; Cao, H.; Chu, S.; Zhang, X.; Xu, Q.; Yu, L. Catal. Sci. Technol. 2018, 8, 5017.
[2]
(d) Li, P.; Cao, K.; Jing, X.; Liu, Y.; Yu, L. New J. Chem. 2021, 45, 17241.
[3]
Yu, L.; Bai, Z.; Zhang, X.; Ding, Y.; Xu, Q. Catal. Sci. Technol. 2016, 6, 1804.
[4]
Li, P.; Qi, Z.; Yu, L.; Zhou, H. Catal. Sci. Technol. 2022, 12, 2241.
[5]
(a) Sun, H.; Shi, Y.; Fu, W.; Yu, L. ChemistrySelect 2021, 6, 7599.
[5]
(b) Tong, Q.; Zhao, S.; Liu, Y.; Xu, B.; Yu, L.; Fan, Y. Appl. Organomet. Chem. 2020, 34, e5380.
[5]
(c) Yang, Y.; Xu, B.; He, J.; Shi, J.; Yu, L.; Fan, Y. Appl. Organomet. Chem. 2019, 33, e5204.
[5]
(d) Yang, Y.; Li, M.; Cao, H.; Zhang, X.; Yu, L. Mol. Catal. 2019, 474, 110450.
[5]
(e) Fan, X.; Yao, Y.; Xu, Y.; Yu, L.; Qiu, C. ChemCatChem 2019, 11, 2596.
[5]
(f) Wang, F.; Xu, L.; Sun, C.; Yu, L.; Xu, Q. Appl. Organomet. Chem. 2018, 32, e4505.
[5]
(g) Zhao, S.; Xu, B.; Yu, L.; Fan, Y. Chin. Chem. Lett. 2018, 29, 884.
[5]
(h) Zhao, S.; Xu, B.; Yu, L.; Fan, Y. Chin. Chem. Lett. 2018, 29, 475.
[5]
(i) Wang, Y.; Wu, Z.; Li, Q.; Zhu, B.; Yu, L. Catal. Sci. Technol. 2017, 7, 3747.
[6]
(a) Zhu, Z.; Sun, S.; Jing, X. Chem. Pap. 2022, 76, 401.
[6]
(b) Wang, Q.; Li, P.; Li, T.; Liu, M.; Zuo, S.; Liu, J.; Xu, L.; Zhang, X.; Yu, L. Ind. Eng. Chem. Res. 2021, 60, 8659.
[6]
(c) Xiao, X.; Shao, Z.; Yu, L. Chin. Chem. Lett. 2021, 33, 2933.
[6]
(d) Zhou, W.; Li, P.; Liu, J.; Yu, L. Ind. Eng. Chem. Res. 2020, 59, 10763.
[6]
(e) Chu, S.; Cao, H.; Chen, T.; Shi, Y.; Yu, L. Catal. Commun. 2019, 129, 105730.
[7]
Rayman, M. P. Lancet 2012, 379, 1256.
[8]
(a) Zhu, Z.; Sun, S.; Tang, S.; Chu, S.; Zhang, X. Mol. Catal. 2021, 515, 111923.
[8]
(b) Chen, X.; Mao, J.; Liu, C.; Chen, C.; Cao, H.; Yu, L. Chin. Chem. Lett. 2020, 31, 3205.
[8]
(c) Liu, C.; Mao, J.; Zhang, X.; Yu, L. Catal. Commun. 2020, 133, 105828.
[9]
Xia, W.; Sun, J.; Zeng, X.; Wang, P.; Luo, M.; Dong, J.; Yu, H. ACS Omega 2020, 5, 2205.
[10]
(a) Zhang, J.; Cao, K.; Zhang, X.; Zhang, Q. Appl. Organomet. Chem. 2020, 34, e5377.
[10]
(b) Zhu, Z.; Wang, W.; Zeng, L.; Zhang, F.; Liu, J. Catal. Commun. 2020, 142, 106031.
[11]
(a) Zeng, Y.; Chen, T.; Zhang, X.; Chen, Y.; Zhou, H.; Yu, L. Appl. Organomet. Chem. 2022, 36, e6658.
[11]
(b) Li, H.; Jing, X.; Shi, Y.; Yu, L. React. Chem. Eng. 2021, 6, 119.
[11]
(c) Wang, F.; Chen, T.; Shi, Y.; Yu, L. Asian J. Org. Chem. 2021, 10, 614.
[11]
(d) Wang, F.; Yang, C.; Shi, Y.; Yu, L. Mol. Catal. 2021, 514, 111849.
[12]
(a) Yu, L.; Ye, J.; Zhang, X.; Ding, Y.; Xu, Q. Catal. Sci. Technol. 2015, 5, 4830.
[12]
(b) Yu, L.; Chen, F.; Ding, Y. ChemCatChem 2016, 8, 1033.
[12]
(c) Cao, H.; Liu, M.; Qian, R.; Zhang, X.; Yu, L. Appl. Organomet. Chem. 2019, 33, e4599.
[12]
(d) Cao, H.; Chen, T.; Yang, C.; Ye, J.; Zhang, X. Synlett 2019, 30, 1683.
[12]
(e) Gao, G.; Han, J.; Yu, L.; Xu, Q. Synlett 2019, 30, 1703.
[13]
(a) Yu, L.; Cao, H.; Zhang, X.; Chen, Y.; Yu, L. Sustainable Energy Fuels 2020, 4, 730.
[13]
(b) Zhang, X.; Zhou, R.; Q, Z.; Chen, L.; Zhou, H. React. Chem. Eng. 2022, 7, 1990.
[14]
(a) Yu, L.; Wu, Y.; Cao, H.; Zhang, X.; Shi, X.; Luan, J.; Chen, T.; Pan, Y.; Xu, Q. Green Chem. 2014, 16, 287.
[14]
(b) Zhang, X.; Sun, J.; Ding, Y.; Yu, L. Org. Lett. 2015, 17, 5840.
[14]
(c) Chen, C.; Cao, Z.; Zhang, X.; Li, Y.; Yu, L.; Jiang, X. Chin. J. Chem. 2020, 38, 1045.
[14]
(d) Cao, Z.; Deng, X.; Chen, C.; Liu, Y.; Yu, L.; Jiang, X. React. Chem. Eng. 2021, 6, 454.
[15]
(a) Huynh, L.; Tirtowidjojo, M.; Truong, T. Chem. Phys. Lett. 2009, 469, 81.
[15]
(b) Yu, L.; Huang, Y.; Bai, Z.; Zhu, B.; Ding, K.; Chen, T.; Ding, Y.; Wang, Y. J. Chin. Chem. Soc. 2015, 62, 479.
[15]
(c) Cedrowski, J.; Litwinienko, G.; Baschieri, A.; Amorati, R. Chem. Eur. J. 2016, 22, 16441.
[15]
(d) Wadnerkar, N.; Gueskine, V.; Gliowacki, E.; Zozoulenko, I. J. Phys. Chem. A 2020, 124, 9605.
[16]
(a) Deng, X.; Qian, R.; Zhou, H.; Yu, L. Chin. Chem. Lett. 2021, 32, 1029.
[16]
(b) Wang, T.; Jing, X.; Chen, C.; Yu, L. J. Org. Chem. 2017, 82, 9342.
[16]
(c) Jing, X.; Yuan, D.; Yu, L. Adv. Synth. Catal. 2017, 359, 1194.
[16]
(d) Jing, X.; Wang, T.; Ding, Y.; Yu, L. Appl. Catal. A-Gen. 2017, 541, 107.
[16]
(e) Yu, L.; Wang, J.; Chen, T.; Wang, Y.; Xu, Q. Appl. Organomet. Chem. 2014, 28, 652.
[17]
(a) Chen, C.; Zhang, X.; Cao, H.; Wang, F.; Yu, L.; Xu, Q. Adv. Synth. Catal. 2019, 361, 603.
[17]
(b) Cao, H.; Zhu, B.; Yang, Y.; Xu, L.; Yu, L.; Xu, Q. Chin. J. Catal. 2018, 39, 899.
[17]
(c) Zhang, D.; Huang, Y.; Zhang, E.; Yi, R.; Chen, C.; Yu, L.; Xu, Q. Adv. Synth. Catal. 2018, 360, 784.
[17]
(d) Zhang, X.; Ye, J.; Yu, L.; Shi, X.; Zhang, M.; Xu, Q.; Lautens, M. Adv. Synth. Catal. 2015, 357, 955.
[18]
(a) Liu, M.; Zhang, X.; Chu, S.; Ge, Y.; Huang, T.; Liu, Y.; Yu, L. Chin. Chem. Lett. 2022, 33, 205.
[18]
(b) Cao, H.; Ma, R.; Chu, S.; Xi, J.; Yu, L.; Guo, R. Chin. Chem. Lett. 2021, 32, 2761.
[18]
(c) Mao, X.; Li, P.; Li, T.; Zhao, M.; Chen, C.; Liu, J.; Wang, Z.; Yu, L. Chin. Chem. Lett. 2020, 31, 3276.
[18]
(d) Cao, H.; Yang, Y.; Chen, X.; Liu, J.; Chen, C.; Yuan, S.; Yu, L. Chin. Chem. Lett. 2020, 31, 1887.
[19]
Chen, C.; Cao, Y.; Wu, X.; Cai, Y.; Liu, J.; Xu, L.; Ding, K.; Yu, L. Chin. Chem. Lett. 2020, 31, 1078.
[20]
(a) Xiao, X.; Guan, C.; Xu, J.; Fu, W.; Yu, L. Green Chem. 2021, 23, 4647.
[20]
(b) Cao, H.; Qian, R.; Yu, L. Catal. Sci. Technol. 2020, 10, 3113.
[20]
(c) Singh, F. V.; Wirth, T. Catal. Sci. Technol. 2019, 9, 1073.
[20]
(d) Shao, L.; Li, Y.; Lu, J.; Jiang, X. Org. Chem. Front. 2019, 6, 2999.
[20]
(e) Zheng, Y.; Wu, A.; Ke, Y.; Cao, H.; Yu, L. Chin. Chem. Lett. 2019, 30, 937.
[20]
(f) Guo, R.; Liao, L.; Zhao, X. Molecules 2017, 22, 835.
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