SIOC English
有机化学
高级检索

有机化学 >

2025 , Vol. 45 >Issue 4: 1360 - 1368

DOI: https://doi.org/10.6023/cjoc202406031

研究论文

电化学促进的甘氨酸衍生物酯交换反应

  • 尤晓琴 ,
  • 黄克金 ,
  • 庄诗怡 ,
  • 刘晨江 ,
  • 金伟伟
展开
  • a 中国计量大学生命科学学院 浙江省特色农产品品质及危害物控制技术重点实验室 杭州 310018
    b 新疆大学化学学院 乌鲁木齐 830017
† 共同第一作者

收稿日期: 2024-06-21

  修回日期: 2024-09-15

  网络出版日期: 2024-10-11

基金资助

国家自然科学基金(22161044); 中国计量大学启动基金(01101-231067)

收起

Electrochemically Promoted Transesterification Reaction of Glycine Derivatives

  • Xiaoqin You ,
  • Kejin Huang ,
  • Shiyi Zhuang ,
  • Chenjiang Liu ,
  • Weiwei Jin
Expand
  • a Key Laboratory of Special Agricultural Products Quality and Hazards Controlling Technology of Zhejiang Province, College of Life Sciences, China Jiliang University, Hangzhou 310018
    b College of Chemistry, Xinjiang University, Urumqi 830017
† These authors contributed equally to this work.
* E-mail: ;
;

Received date: 2024-06-21

  Revised date: 2024-09-15

  Online published: 2024-10-11

Supported by

National Natural Science Foundation of China(22161044); Scientific Research Foundation of China Jiliang University(01101-231067)

Fold

摘要

报道了一例电化学促进的甘氨酸衍生物的酯交换反应. 在未分隔的电解池中, 以溴化钠作为电解质、廉价易得的镍板与石墨板作为电极材料, 甘氨酸衍生物能够与醇类溶剂发生酯交换反应, 进一步合成结构更加多样化的甘氨酸酯衍生物, 收率最高可达88%. 该反应条件温和, 无需过渡金属、酸和碱等催化剂参与, 符合绿色化学理念. 此外, 在克级规模实验中, 该反应可获得1.32 g酯交换产物, 表明其在有机电合成领域具有潜在的应用价值.

关键词： 电化学; 甘氨酸衍生物; 酯交换反应

本文引用格式

尤晓琴 , 黄克金 , 庄诗怡 , 刘晨江 , 金伟伟 . 电化学促进的甘氨酸衍生物酯交换反应[J]. 有机化学, 2025 , 45(4) : 1360 -1368 . DOI: 10.6023/cjoc202406031

Abstract

In an undivided cell, using N-phenylglycine ethyl ester as the model substrate, the reaction conditions were optimized. The results showed that the optimal reaction conditions were at room temperature and air condition, using nickel and graphite plate as anode and cathode materials respectively, 2.0 equiv. of NaBr as the electrolyte, ethylene glycol (EG)/dime- thyl-acetamide (DMA) (V∶V=3∶1) as the mixed solvent, and reacting under 6 mA constant current for 3 h. The transesterification reaction could afford various corresponding glycine derivatives up to 88% yield. This mild reaction condition without adding any transition metal, acid or base, was complied with the concept of green chemistry. In addition, 1.32 g of esterification products was successfully synthesized in a gram scale experiment, which also demonstrated the potential value of electrochemical transesterification of glycine derivatives.

Key words： electrochemistry; glycine derivatives; transesterification

参考文献

[1]
Teng, B.; Shi, J.; Yao, C. Green Chem. 2018, 20, 2465.
[2]
Sereda, G.; Pothula, S.; Dreessen, J. Synth. Commun. 2010, 40, 1312.
[3]
Kan-nari, N.; Okamura, S.; Fujita, S.; Ozaki, J.; Arai, M. Adv. Synth. Catal. 2010, 352, 1476.
[4]
Shinada, T.; Ohfune, Y.; Hamada, M.; Miyoshi, K.; Higashino, M.; Umezawa, T. Synlett 2010, 2010, 2141.
[5]
Rathore, P. S.; Advani, J.; Rathore, S.; Thakore, S. J. Mol. Catal. A: Chem. 2013, 377, 129.
[6]
Opalade, A. A.; Karmakar, A.; Rúbio, G. M. D. M.; Pombeiro, A. J. L.; Gerasimchuk, N. Inorg. Chem. 2017, 56, 13962.
[7]
Yang, H. S.; Macha, L.; Ha, H. J.; Yang, J. W. Org. Chem. Front. 2021, 8, 53.
[8]
Mittapelli, L. L.; Gore, K. R. Catal. Commun. 2021, 149, 106194.
[9]
Francke, R.; Little, R. D.; Inagi, S. ChemElectroChem 2019, 6, 4065.
[10]
Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099.
[11]
Leech, M. C.; Garcia, A. D.; Petti, A.; Dobbs, A. P.; Lam, K. React. Chem. Eng. 2020, 5, 977.
[12]
Chiarotto, I.; Feroci, M.; Sotgiu, G.; Inesi, A. Eur. J. Org. Chem. 2012, 2013, 326.
[13]
Góes, A. C. S. F.; Souza, O.; Oliveira, R. T. S.; Cesarino, I.; Machado, S. A. S.; Eguiluz, K. I. B.; Cavalcanti, E. B.; Salazar-Banda, G. R. Chem. Eng. Commun. 2014, 202, 1406.
[14]
Pirsaheb, M.; Cheraghianfard, S.; Pakravan, P.; Mohammadi, T.; Vafaeifard, M.; Akhbari, A.; Mansouri, A. Desalin. Water Treat. 2017, 88, 268.
[15]
Martini, M. B.; Adam, C. G.; Fernández, J. L. Mol. Catal. 2021, 513, 111821.
[16]
Huang, K. J.; Cai, J. B.; Wang, R. G.; Zhang, Y. H.; Wang, B.; Xia, Y.; Jin, W. W.; Li, X. Y.; Liu, C. J. Chin. J. Org. Chem. 2024, 44, 989 (in Chinese).
[16]
(黄克金, 蔡金博, 王瑞革, 张永红, 王斌, 夏昱, 金伟伟, 李新勇, 刘晨江, 有机化学, 2024, 44, 989.)
[17]
Wang, R. G.; Wang, J.; Zhang, Y. H.; Wang, B.; Xia, Y.; Xue, F.; Jin, W. W.; Liu, C. J. Adv. Synth. Catal. 2023, 365, 900.
[18]
Wang, R.; Dong, X.; Zhang, Y.; Wang, B.; Xia, Y.; Abdukader, A.; Xue, F.; Jin, W.; Liu, C. Chem.-Eur. J. 2021, 27, 14931.
[19]
Zhang, S.; Li, L.; Wu, P.; Gong, P.; Liu, R.; Xu, K. Adv. Synth. Catal. 2018, 361, 485.
[20]
Cardoso, D. S. P.; ?ljuki?, B.; Santos, D. M. F.; Sequeira, C. A. C. Org. Process Res. Dev. 2017, 21, 1213.
[21]
Xu, P. C.; Qian, S.; Meng, X.; Zheng, Y.; Huang, S. Org. Lett. 2023, 26, 2806.
[22]
Hu, Y.; Liu, X.; Feng, C.; Wang, J.; Li, M.; Shen, Z. Adv. Synth. Catal. 2024, 366, 2020.
[23]
Kumar, R.; Dutt, S.; Banerjee, P. Chem. Commun. 2024, 60, 4246
[24]
Li, D.; Chen, L.; Jin, Y.; Wang, X.; Liu, L.; Li, Y.; Chen, G.; Wu, G.; Qin, Y.; Yang, L.; Wang, M.; Zhao, L.; Xu, Z.; Wen, J. Green Chem. 2023, 25, 4656.
[25]
Ruan, C.; Liu, C.; Hu, H.; Guo, X. L.; Jiang, B. P.; Liang, H.; Shen, X. C. Chem. Sci. 2019, 10, 4699.
[26]
Black, E.; Breed, J.; Breeze, A. L.; Embrey, K.; Garcia, R.; Gero, T. W.; Godfrey, L.; Kenny, P. W.; Morley, A. D.; Minshull, C. A.; Pannifer, A. D.; Read, J.; Rees, A.; Russell, D. J.; Toader, D.; Tucker, J. Bioorg. Med. Chem. Lett. 2005, 15, 2503.
[27]
Fu, X. L.; Wu, S. H. Synth. Commun. 1997, 27, 1677.
Options
文章导航

/

〈 〉