Citation: Guan Aiying, Zhao Yu, Wang Weiwei, Liu Xinlei, Wang Mingan. Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(10): 2767-2774. doi: 10.6023/cjoc201804024 shu

Synthesis and Fungicidal Activity of 3-Acetyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one Derivatives

Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing 100193

Corresponding author: Wang Mingan, wangma@cau.edu.cn
Received Date: 13 April 2018
Revised Date: 11 May 2018
Available Online: 5 October 2018
Fund Project: the National Natural Science Foundation of China 21772229Project supported by the National Natural Science Foundation of China (No. 21772229)

Figures(2)

The diversity-orientied synthesis strategy was utilized to diversely derive from the carbonyl of 3-acetyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one, a series of novel 3-acetyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one derivatives were synthesized. The preliminary in vivo and in vitro bioassay results showed that some compounds exhibited excellent fungicidal activity against phytopathagens, such as 3-allyloxyethyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one (7) had 100% control rates against Pseudoperonospora cubensis and Puccinia polysora at the concentration of 400 μg/mL.
- diversity-orientied synthesis,
- 3-acetyl-4-phenyl-1-oxaspiro[4, 5]dec-3-en-2-one,
- fungicidal activity,
- phytopathagen
1. [1]
  Schreiber, S. L. Science 2000, 287, 1964. doi: 10.1126/science.287.5460.1964
2. [2]
  Garcia-Castro, M.; Zimmermann, S.; Sankar, M. G.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 7586. doi: 10.1002/anie.201508818
3. [3]
  Maiti, B.; Chanda, K. RSC Adv. 2016, 6, 50384. doi: 10.1039/C6RA06930D
4. [4]
  Huang, L.; Ye, L.; Li, X.-H.; Li, Z.-L.; Lin, J.-S.; Liu, X.-Y. Org. Lett. 2016, 18, 5284. doi: 10.1021/acs.orglett.6b02599
5. [5]
  Han, Z.-G.; Miao, C.-B.; Shi, F.; Ma, N.; Zhang, G.; Tu, S.-J. J. Comb. Chem. 2010, 12, 16. doi: 10.1021/cc900030e
6. [6]
  Guan, A. Y.; Liu, C. L.; Yang, X. P.; Dekeyser, M. Chem. Rev. 2014, 114, 7079. doi: 10.1021/cr4005605
7. [7]
  Liu, C. L.; Guan, A. Y.; Yang, J. D.; Chai, B. S.; Li, M.; Li, H. C.; Yang, J. C.; Xie, Y. J. Agric. Food Chem. 2016, 64, 45. doi: 10.1021/jf5054707
8. [8]
  Guan, A. Y.; Liu, C. L.; Sun, X. F.; Xie, Y.; Wang, M. A. Bioorg. Med. Chem. 2016, 24, 342. doi: 10.1016/j.bmc.2015.09.031
9. [9]
  Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-Kintscher, U.; Thielert, W.; Wolfel, K.; Haas, M.; Kunz, K.; Raupach, G. Pest. Manage. Sci. 2015, 71, 850. doi: 10.1002/ps.3932
10. [10]
  Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem. 2016, 24, 317. doi: 10.1016/j.bmc.2015.12.014
11. [11]
  Leite, L.; Jansone, D.; Veveris, M.; Cirule, H.; Popelis, J.; Melikyan, G.; Avetisyan, A.; Lukevics, E. Eur. J. Med. Chem. 1999, 34, 859. doi: 10.1016/S0223-5234(99)00206-8
12. [12]
  Melikyan, G. S.; Hovhannisyan, A. A.; Hayotsyan, S. S. Synth. Commun. 2012, 42, 2267. doi: 10.1080/00397911.2011.555591
13. [13]
  Lei, J. P.; Han, J. T.; Xu, Z. H.; Dong, H. B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 1993(in Chinese).
14. [14]
  Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740. doi: 10.3390/molecules200813740
15. [15]
  Zhao, Y.; Tang, B.; Guan, A. Y.; Wang, W. W.; Zhang, Z. H.; Wang, M. A. Synthesis 2017, 49, 4663. doi: 10.1055/s-0036-1588463
16. [16]
  Tang, B.; Guan, A. Y.; Zhao, Y.; Jiang, J. Z.; Wang, M. A. Chin. J. Chem. 2017, 35, 1133. doi: 10.1002/cjoc.v35.7
17. [17]
  Zhao, Y.; Tang, B.; Liu, X. L.; Li, W. Z.; Huang, M. Y.; Wang, M. A. Chin. J. Org. Chem. 2017, 37, 975(in Chinese).
18. [18]
  Prat, I.; Font, D.; Company, A.; Junge, K.; Ribas, X.; Beller, M.; Costas, M. Adv. Synth. Catal. 2013, 355, 947. doi: 10.1002/adsc.201200938
19. [19]
  Carceller, G. E.; Salas, S. J.; Alvarez, F. C.; Andreu, A. J. A. WO 2003084984, 2003[Chem. Abstr. 2003, 139, 323795].
20. [20]
  Guenther, M.; Lategahn, J.; Juchum, M.; Doering, E.; Keul, M.; Engel, J.; Tumbrink, H. L.; Rauh, D.; Laufer, S. J. Med. Chem. 2017, 60, 5613. doi: 10.1021/acs.jmedchem.7b00316
21. [21]
  Zhang, C. Y.; Chen, S. C.; Wang, D. Q.; Wang, M. A. Acta Chim. Sinica 2010, 68, 989(in Chinese).
22. [22]
  Zan, N. N.; Wan, F. X.; Wang, S. C.; Zhang, J. H.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 1537(in Chinese).
23. [23]
  Yang, Y. Z.; Lin, D. Y.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 100(in Chinese).
24. [24]
  Guan, A. Y.; Liu, C. L.; Chen, W.; Yang, F.; Xie. Y.; Zhang, J. B.; Li, Z. N.; Wang, M. A. J. Agric. Food Chem. 2017, 65, 1272. doi: 10.1021/acs.jafc.6b05580
25. [25]
  Guan, A. Y.; Wang, M. A.; Yang, J. L.; Wang, L. Z.; Xie, Y.; Lan, J.; Liu, C. L. J. Agric. Food Chem. 2017, 65, 10829. doi: 10.1021/acs.jafc.7b03898
26. [26]
  Guan, A. Y.; Wang, M. A.; Chen, W.; Yang, F.; Yang, J. L.; Zhao, Y.; Li, Z. N.; Liu, C. L. J. Fluorine Chem. 2017, 201, 49. doi: 10.1016/j.jfluchem.2017.08.008
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
3. [3]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
4. [4]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
5. [5]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
6. [6]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-. doi: 10.1016/j.actphy.2025.100052
7. [7]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
8. [8]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
9. [9]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
10. [10]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
11. [11]
  Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . 具有富电子Pt^δ^-壳层的空心AgPt@Pt核壳催化剂：提升光催化H₂O₂生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-. doi: 10.1016/j.actphy.2025.100081
12. [12]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
13. [13]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
14. [14]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
17. [17]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
18. [18]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
19. [19]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
20. [20]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(675)
HTML views(85)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142