Citation: Acid Wang Weiwei, Zhao Yu, Liu Xinlei, Geng Rui, Wang Mingan. Synthesis of (E)-3-Aryl-7-methylocta-2, 6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2, 6-dienoic[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1129-1135. doi: 10.6023/cjoc201809018 shu

Synthesis of (E)-3-Aryl-7-methylocta-2, 6-dienoic Acid via Stereoselective Mizoroki-Heck Arylation of (E)-7-Methylocta-2, 6-dienoic

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Mingan, wangma@cau.edu.cn
Received Date: 12 September 2018
Revised Date: 18 October 2018
Available Online: 5 April 2018
Fund Project: the National Natural Science Foundation of China 21772229Project supported by the National Natural Science Foundation of China (No. 21772229)

Figures(5)

Stereoselective Mizoroki-Heck arylation of (E)-7-methylocta-2, 6-dienoic acid with aryl iodide catalyzed by Pd(OAc)₂ and P(o-MeC₆H₄)₃ was optimized, and the yields were improved under the condition of excess Et₃N both as the base and solvent with reduced amount of catalysts. Twenty (E)-3-aryl-7-methylocta-2, 6-dienoic acids were directly synthesized via Mizoroki-Heck arylation in 37%~68% isolated yields at reflux temperature. Their structures were characterized by IR, ¹H, ¹³C NMR, HR-ESI-MS data and X-ray diffraction.
- (E)-3-aryl-7-methylocta-2, 6-dienoic acid,
- Mizoroki-Heck arylation,
- configuration,
- synthesis
1. [1]
  (a) Kamal, A.; Balakishan, G.; Ramakrishna, G.; Basha, S. T.; Sreekanth, K.; Balakrishna, M.; Dastagiri, D.; Kalivendi, S. V. Eur. J. Med. Chem. 2010, 45, 3870.
  (b) Xiao, Y. M.; Yang, X. L.; Li, B.; Yuan, H. Z.; Wan, S. Q.; Xu, Y. J.; Qin, Z. H. Molecules 2011, 16, 8945.
  (c) Debnath, B.; Samanta, S.; Roy, K.; Jha, T. Bioorg. Med. Chem. 2003, 11, 1615.
  (d) Zhen, Y. S.; Jiang, X. F. Anti-cancer Drug 2000, 11, 49.
2. [2]
  (a) Kuhn, P. J.; Pitt, D.; Lee, S. A.; Wakley, G.; Shepard, A. N. Mycol. Res. 1991, 95, 333.
  (b) Liu, W. C.; Liu, C. L. Pesticides 2002, 41, 8.
  (c) Mu, C. W.; Yuan, H. Z.; Li, N.; Fu, B.; Xiao, Y. M.; Ma, Y. Q.; Qi, S. H.; Qin, Z. H. Chem. J. Chin. Univ. 2007, 28, 1902.
3. [3]
  (a) Pham, T.-N.; Bordage, S.; Pudlo, M.; Demougeot, C.; Thai, K.-M.; Girard-Thernier, C. Int. J. Mol. Sci. 2016, 17, 1656.
  (b) Ridwan, A. Y.; Matoba, R.; Wu, J.; Choi, J.-H.; Hirai, H.; Kawagishi, H. Tetrahedron Lett. 2018, 59, 2559.
  (c) Prasanthi, G.; Prasad, K.; Bharathi, K. Med. Chem. Res. 2018, 27, 1599.
  (d) Sall, C.; Aye, M.; Bottzeck, O.; Praud, A.; Blache, Y. Bioorg. Med. Chem. Lett. 2018, 28, 155.
  (e) Yang, M. Y.; Dong, H. B.; Jiang, J. Z.; Wang, M. A. Molecules 2015, 20, 21023.
4. [4]
  Gallardo, G. L.; Pena, N. I.; Cabrera, G. M. Phytochem. Lett. 2008, 1, 155.
5. [5]
  Yang, Y.; Jiang, J. Z.; Qimei, L. B.; Yan, X. J.; Zhao, J. X.; Yuan, H. Z.; Qin, Z. H.; Wang, M. A. Molecules 2010, 15, 7075. doi: 10.3390/molecules15107075
6. [6]
  Burton, A. F., McLean, D. US 5175190, 1992.
7. [7]
  Chen, J.; Zhu, C. L.; Xu, H. Y.; Ni, X.; Yang, P. M. Chin. J. Pharm. 2010, 41, 504.
8. [8]
  Lee, K. Y.; Kim, S. H.; Sung, S. H. Planta Med. 2008, 74, 867. doi: 10.1055/s-2008-1074552
9. [9]
  Dong, H. B.; Yang, M. Y.; Jiang, J. Z.; Wang, M. A. J. Asian Nat. Prod. Res. 2013, 15, 880. doi: 10.1080/10286020.2013.803474
10. [10]
  Zhao, J.; Dong, H. B.; Yang, M. Y.; Du, J.; Jiang, J. Z.; Wang, M. A. J. Asian Nat. Prod. Res. 2014, 16, 312. doi: 10.1080/10286020.2013.879121
11. [11]
  Dong, H. B.; Yang, M. Y.; Tang, B.; Wang, M. A. Chin. J. Org. Chem. 2014, 34, 2350 (in Chinese).
12. [12]
  Wang, M. A.; Dong, H. B.; Yang, M. Y. CN 103012357, 2012.
13. [13]
  (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
  (b) Heravi, M. M.; Zadsirjan, V.; Esfandyari, M.; Lashaki, T. B. Tetrahedron: Asymmetry 2017, 28, 987.
14. [14]
  Dong, H. B.; Yang, M. Y.; Zhang, X. T.; Wang, M. A. Tetrahedron: Asymmetry 2014, 25, 610. doi: 10.1016/j.tetasy.2014.03.006
15. [15]
  Wang, W. W.; Zhang, X. T.; Zhao, Y.; Liu, X. L.; Zhang, Z. H.; Wang, M. A. Chin. Chem. Lett. 2018, 29, 1872. doi: 10.1016/j.cclet.2018.02.006
16. [16]
  Dong, H. B. Ph.D. Dissertation, China Agricultural University, 2014.
17. [17]
  (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (b) Jia, C. G.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.
  (c) Fukuyama, T.; Arai, M.; Matsubara, H.; Ryu, I. J. Org. Chem. 2004, 69, 8105.
  (d) Alacid, E.; Najera, C. ARKIVIC 2008, VIII, 50.
  (e) Sun, P.; Qu, X.; Li, T.; Zhu, Y.; Yang, H.; Xing, Z.; Mao, J. Synlett 2012, 23, 150.
  (f) Lasch, R.; Fehler, S. K.; Heinrich, M. R. Org. Lett. 2016, 18, 1586.
  (g) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
18. [18]
  (a) Patel, B. A.; Dickerson, J. E.; Heck, R. F. J. Org. Chem. 1978, 43, 5018.
  (b) Solabananvar, S. B.; Desai, U. V.; Mane, R. B. Green Chem. 2002, 4, 347.
  (c) Li, Y.; Lin, X. F.; Liu, M. Y.; Zhang, L. L.; Jin, A. P.; Lu, J. M. J. Chem. Res. 2013, 37, 294.
  (d) Wang, Y. P.; Lee, H. M. J. Organomet. Chem. 2015, 791, 90.
  (e) Ibrahim, M. B.; Suleiman, R.; Fettouhi, M.; Ali, B. E. Transit. Med. Chem. 2017, 42, 1.
19. [19]
  (a) Morris, C. L.; Hu, Y.; Head, G. D.; Brown, L. J.; Whittingham, W. G.; Brown, R. C. D. J. Org. Chem. 2009, 74, 981.
  (b) Domingo, L. R.; Gil, S.; Parra, M.; Saez, J. A.; Torres, M. Tetrahedron 2003, 59, 6233.
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]
  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
3. [3]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
4. [4]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
5. [5]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
6. [6]
  Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
7. [7]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
8. [8]
  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
9. [9]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
10. [10]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
11. [11]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
12. [12]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
13. [13]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336
14. [14]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
15. [15]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
16. [16]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
17. [17]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
18. [18]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
19. [19]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
20. [20]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(578)
HTML views(37)

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