Citation: Zhao Jianyang, Zheng Zihua, Huang Qingfei, Deng Jingen, Zhu Jin, Wang Qiwei. A Method for the Synthesis of the Isorhapontigenin and the Stilbene Compounds in Similar Structures[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 648-652. doi: 10.6023/cjoc201508027 shu

A Method for the Synthesis of the Isorhapontigenin and the Stilbene Compounds in Similar Structures

Zhao Jianyang ^a,b ,
Zheng Zihua ^a,b ,
Huang Qingfei ^a ,
Deng Jingen ^c ,
Zhu Jin ^a,, ,
Wang Qiwei ^a,,

1.
a Chengdu Institute of Organic Chemistry, Chinese Academy of Science, Chengdu 610041;
2.
b University of Chinese Academy of Sciences, Beijing 100049;
3.
c West China School of Pharmacy Sichuan University, Chengdu 610041

Corresponding author: Zhu Jin, Wang Qiwei,
Received Date: 27 August 2015
Available Online: 31 October 2015
Fund Project:

A method for the synthesis of the isorhapontigenin and the stilbene compounds in similar structures was developed. Using 3,5-dihydroxybenzoic acid as starting material, benzyl protecting the phenolic hydroxyl, via the Wittig-Horner reaction to construct the trans stilbene structure, and then debenzylation under the palladium on carbon/ammonium formate system condition, the isorhapontigenin could be obtained in the yield of up to 48%. The catalytic system was successfully applied in the synthesis of a series of hydroxyl stilbene compounds, which could achieve good results. All the reactions worked under mild conditions and obtained in good yield. Furthermore the materials were of cheap and less toxicity. It provided us a simple way to synthesize hydroxyl stilbene compounds in large scale.
- isorhapontigenin,
- hydroxyl stilbene compounds,
- palladium on carbon/ammonium formate,
- debenzylation
1. [1]
  [1] Wang, Q. L.; Lin, M.; Liu, G. T. Chin. Pharm. J. 2001, 36, 810 (in Chinese). (王庆利, 林茂, 刘耕陶, 中国药学杂志, 2001, 36, 810.)
2. [2]
  [2] Iliya, I.; Ali, Z.; Tanaka, T.; Iinuma, M.; Furusawa, M.; Nakaya, K.-I.; Murata, J.; Darnaedi, D.; Matsuura, N.; Ubukata, M. Phytochemistry 2003, 62, 601.
3. [3]
  [3] Matsuda, H.; Tewtrakul, S.; Morikawa, T.; Yoshikawa, M. Bioorg. Med. Chem. 2004, 12, 4871.
4. [4]
  [4] Li, H.-L.; Wang, A.-B.; Huang, Y.; Liu, D.-P.; Wei, C.; Williams, G. M. Free Radical Biology Med. 2005, 38, 243.
5. [5]
  [5] Liu, A.-L.; Yang, F.; Zhu, M.; Zhou, D.; Lin, M.; Lee, S. M.-Y. Planta Med. 2010, 76, 1874.
6. [6]
  [6] Fang,Y.; Hou, Q.; Pang, H.-M. Chin. Pharm. J. 2014, 49, 653 (in Chinese). (方勇, 侯琦, 潘宏铭, 中国药学杂志, 2014, 49, 653.)
7. [7]
  [7] He, P.; Liu, Z.-M.; Liao, Z.-Y. Anat. Res. 2005, 27, 279 (in Chinese). (何平, 刘振明, 廖振裕, 解剖学研究, 2005, 27, 279.)
8. [8]
  [8] Li, W.-L.; He, K.-K.; Li, Y.; Hou, Z.-J. Acta Chim. Sinica 2005, 63, 1607 (in Chinese). (李文玲, 何侃侃, 李瀛, 侯自杰, 化学学报, 2005, 63, 1607.)
9. [9]
  [9] Bieg, T.; Szeja, W. Synth. Commun. 1985, 15, 76.
10. [10]
  [10] Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950.
11. [11]
  [11] Ranu, B. C.; Sarkar, A. Tetrahedron Lett. 1994, 35(46), 8649.
12. [12]
  [12] Negi, A. S.; Darokar, M.-P.; Chattapodhyay, S.-K.; Grag, A.; Bhattacharya, A.-K.; Srivastava, V.; Khanuja, S. P. S. Bioorg. Med. Chem. Lett. 2005, 15, 1243.
13. [13]
  [13] Negi, A. S.; Chattapodhyay, S.-K.; Srivastava, S.; Bhattacharya, A.-K. Synth. Commun. 2005, 35, 15.
14. [14]
  [14] Koolaji, N.; Abdallah, A. M.; Tran, V. H.; Duke, R. K.; Duke, C. C. Eur. J. Med. Chem. 2013, 63, 415.
15. [15]
  [15] Kim, D.-H.; Park, E.-K.; Bae, E.-A.; Han, M.-J. Biol. Pharm. Bull. 2000, 23(7), 830.
16. [16]
  [16] Lee, H.-S.; Lee, B.-W.; Kim, M.-R.; Jun, J.-G. Bull. Korean Chem. Soc. 2010, 31(4), 971.
17. [17]
  [17] Zhou, Y.; Huang, Q.; Huang, T.-K.; Ni, Q.-C.; Zhang, E.-S.; Xu, T.-L.; Yuan, M.; Li, J. Org. Biomol. Chem. 2013, 11, 6967.
18. [18]
  [18] Lonsky, L.; Lonsky, W.; Kratzl, K. Monatsh. Chem. 1976, 107, 685.
19. [19]
  [19] Cheng, J.-C.; Fang, J.-G.; Chen, W.-F.; Zhou, B.; Yang, L.; Liu, Z.-L. Bioorg. Chem. 2006, 34, 142.
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
4. [4]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
5. [5]
  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
6. [6]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
7. [7]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
8. [8]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
11. [11]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
12. [12]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
13. [13]
  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
14. [14]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
15. [15]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
16. [16]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . 卤化物钙钛矿的单双向离子迁移. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-. doi: 10.3866/PKU.WHXB202311011
17. [17]
  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
18. [18]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
19. [19]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
20. [20]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1576)
HTML views(110)

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