Citation: Zhang Di, Xie Xiong, Feng Jinsheng, Wen Hongliang. Study on the Synthesis of (+)-Oxocamphor[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 202-206. doi: 10.6023/cjoc201506023 shu

Study on the Synthesis of (+)-Oxocamphor

1.
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081

Corresponding author: Wen Hongliang, wen.hongliang816@gmail.com; analchemie@bit.edu.cn
Received Date: 17 June 2015
Revised Date: 30 August 2015

Figures(6)

(+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by ¹H NMR, IR and GC-MS. The absolute configuration of 3, 9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.
- (+)-oxocamphor,
- synthesis,
- single crystal
1. [1]
  Homma, H.; Ono, H. Nippon Shonika Gakkai Zasshi 1969, 73(3), 364.
2. [2]
  Fujii, S.; Inada, S.; Yoshida, S. Nippon Juigaku Zasshi 1970, 32(6), 307.
3. [3]
  Guan, D.-W.; Du, P.-G.; Sun, Y.-F. CN 200810050707, 2009 [Chem. Abstr. 2009, 151, 198646].
4. [4]
  Corey, E. J.; Chow, S. W.; Scherrer, R. A. J. Am. Chem. Soc. 1957, 79, 5773. doi: 10.1021/ja01578a049
5. [5]
  Kornblum, N. K.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113. doi: 10.1021/ja01524a080
6. [6]
  Bekish, A. V.; Prokhorevich, K. N.; Kulinkovich, O. G. Eur. J. Org. Chem. 2006, 22, 5069.
7. [7]
  Shao, P.; Li, Z.; Luo, J.-L.; Wang, H.-L.; Qin, J.-G. Synth. Commun. 2005, 35, 49. doi: 10.1081/SCC-200046485
8. [8]
  Dave, P.; Byun, H. S, ; Engel, R. Synth. Commun. 1986, 16, 1343. doi: 10.1080/00397918608056381
9. [9]
  Mukaiyama, S.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 2221. doi: 10.1246/bcsj.54.2221
10. [10]
  Huang, W.-F.; Xiao, W.-J.; Wang, J.-H. Chin. J. Org. Chem. 1986, 6(5), 376 (in Chinese).
11. [11]
  Villorbina, G.; Roura, L.; Camps, F.; Joglar, J.; Fabrias, G. J. Org. Chem. 2003, 68(7), 2820. doi: 10.1021/jo0267100
12. [12]
  Abad, J.-L.; Fabrias, G.; Camps, F. Lipids 2004, 39(4), 397. doi: 10.1007/s11745-004-1244-0
13. [13]
  Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
14. [14]
  Ogura, T.; Usuki, T. Tetrahedron 2013, 69(13), 2807. doi: 10.1016/j.tet.2013.01.065
15. [15]
  Xiao, Q.-C.; Liu, Y.-Q.; Qiu, Y.-T.; Yao, Z.-Y.; Zhou, G.-B.; Yao, Z.-J.; Jiang, S. Bioorg. Med. Chem. Lett. 2011, 21(12), 3613.
16. [16]
  Alfaro-Lopez, J.; Okayama, T.; Hosohata, K.; Davis, P.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. J. Med. Chem. 1999, 42(26), 5359. doi: 10.1021/jm990337f
17. [17]
  Sorensen, M. H.; Nielsen, C.; Nielsen, P. J. Org. Chem. 2001, 66(14), 4878. doi: 10.1021/jo010299j
18. [18]
  Pfitzner, K. E.; Moffatt, J. G. J. Am. Chem. Soc. 1963, 85, 3027.
1. [1]
  Yueshuai Xu , Wei Liu , Xudong Chen , Zhikun Zheng . 水相中制备共价有机框架单晶的实验教学设计. University Chemistry, 2025, 40(6): 256-265. doi: 10.12461/PKU.DXHX202408045
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]
  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
4. [4]
  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
5. [5]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
6. [6]
  Yao Ma , Xin Zhao , Hongxu Chen , Wei Wei , Liang Shen . Progress and Perspective of Perovskite Thin Single Crystal Photodetectors. Acta Physico-Chimica Sinica, 2025, 41(4): 100030-. doi: 10.3866/PKU.WHXB202309045
7. [7]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
8. [8]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
9. [9]
  Qin ZHU , Jiao MA , Zhihui QIAN , Yuxu LUO , Yujiao GUO , Mingwu XIANG , Xiaofang LIU , Ping NING , Junming GUO . Morphological evolution and electrochemical properties of cathode material LiAl_0.08Mn_1.92O₄ single crystal particles. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1549-1562. doi: 10.11862/CJIC.20240022
10. [10]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
11. [11]
  Yu Wang , Shoulei Zhang , Tianming Lv , Yan Su , Xianyu Liu , Fuping Tian , Changgong Meng . Introduce a Comprehensive Inorganic Synthesis Experiment: Synthesis of Nano Zinc Oxide via Microemulsion Using Waste Soybean Oil. University Chemistry, 2024, 39(7): 316-321. doi: 10.3866/PKU.DXHX202311035
12. [12]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
13. [13]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
14. [14]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
15. [15]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
16. [16]
  Hongyan Chen , Yajun Hou , Shui Hu , Zhuoxun Wei , Fang Zhu , Chengyong Su . Construction of Synthetic Chemistry Experiment of the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 58-63. doi: 10.12461/PKU.DXHX202409109
17. [17]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
18. [18]
  Cunming Yu , Dongliang Tian , Jing Chen , Qinglin Yang , Kesong Liu , Lei Jiang . Chemistry “101 Program” Synthetic Chemistry Experiment Course Construction: Synthesis and Properties of Bioinspired Superhydrophobic Functional Materials. University Chemistry, 2024, 39(10): 101-106. doi: 10.12461/PKU.DXHX202408008
19. [19]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
20. [20]
  Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1970)
HTML views(437)

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