Citation: Zhang Xiaoxiang, Lü Chang, Li Ping, Yong Wanxiong, Li Jing, Zhu Xinbao. Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 208-214. doi: 10.6023/cjoc201706030 shu

Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides

Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Corresponding author: Zhang Xiaoxiang, zhangxiaoxiang@njfu.edu.cn Zhu Xinbao, zhuxinbao@njfu.com.cn
Received Date: 23 June 2017
Revised Date: 17 August 2017
Available Online: 15 January 2017
Fund Project: Young Natural Science Foundation of Jiangsu Province BK20130962the Young National Natural Science Foundation of China 21302096Postgraduate Research & Practice Innovation Program of Jiangsu Province KYLX16_0844Young Natural Science Foundation of Jiangsu Province BK20171449Project supported by the Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (Nos. BK20171449, BK20130962), the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYLX16_0844), and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

Figures(3)

The one-pot one-step synthetic method of 4H-3, 1-benzoxazin-4-ones via the gold-catalyzed oxidative rearrangement of 2-alkynyl arylazides has been developed. The desired products were obtained in moderate to excellent yields under mild reaction conditions. In most cases, using acetic acid as solvent the reactions were shown to proceed very fast within 1 h.
- gold-catalyzed,
- oxidative rearrangement,
- one-pot,
- 2-alkynyl arylazides
1. [1]
  (a) Padwal, R. Curr. Opin. Invest. Drugs 2008, 9, 414.
  (b) Eissa, A. M. F. ; El-Sayed, R. J. Heterocycl. Chem. 2006, 43, 1.
  (c) Neumann, U. ; Schechter, N. M. ; Gutschow, M. Bioorg. Med. Chem. 2001, 9, 947.
  (d) Gutschow, M. ; Neumann, U. Bioorg. Med. Chem. 1997, 5, 1935.
  (e) Krantz, A. ; Spencer, R. W. ; Tam, T. F. ; Liak, T. J. ; Copp, L. J. ; Thomas, E. M. ; Raﬀerty, S. P. J. Med. Chem. 1990, 33, 464.
2. [2]
  (a) Krantz, A. ; Spencer, R. W. ; Tam, T. F. ; Liak, T. J. ; Copp, L. J. ; Thomas, E. M. ; Rafferty, S. P. J. Med. Chem. 1990, 33, 464.
  (b) Stein, R. L. ; Strimpler, A. M. ; Viscarello, B. R. ; Wildonger, R. A. ; Mauger, R. C. ; Trainor, D. A. Biochemistry 1987, 26, 4126.
3. [3]
  For some examples, see: (a) Yamada, Y. ; Kato, T. ; Ogino, H. ; Ashina, S. ; Kato, K. Horm. Metab. Res. 2008, 40, 539.
  (b) Padwal, R. Curr. Opin. Invest. Drugs 2008, 9, 414.
4. [4]
  Hedstrom, L.; Moorman, A. R.; Dobbs, J.; Abeles, R. H. Biochemistry 1984, 23, 1753. doi: 10.1021/bi00303a026
5. [5]
  Jarvest, R. L.; Parratt, M. J.; Debouck, C. M.; Gorniak, J. G.; Jennings, L. J.; Serafinowska, H. T.; Strickler, J. E. Bioorg. Med. Chem. Lett. 1996, 6, 2463. doi: 10.1016/0960-894X(96)00455-6
6. [6]
  (a) Li, W. F. ; Wu, X. F. J. Org. Chem. 2014, 79, 10410.
  (b) Yamashita, M. ; Iida, A. Tetrahedron Lett. 2014, 55, 2991.
  (c) Lian, X. L. ; Lei, H. ; Quan, X. J. ; Ren, Z. H. ; Wang, Y. Y. ; . Guan, Z. H. Chem. Commun. 2013, 49, 8196.
  (d) Ge, Z. Y. ; Xu, Q. M. ; Fei, X. D. ; Tang, T. ; Zhu, Y. M. ; Ji, S. J. J. Org. Chem. 2013, 78, 4524.
  (e) Xie, Y. Y. ; Wang, S. P. J. Chem. Res. 2012, 36, 123.
  (f) Wu X. F. ; Neumann, H. ; Beller, M. Chem. Eur. J. 2012, 18, 12599.
  (g) Kumar, R. A. ; Maheswari, C. U. ; Ghantasala, S. ; Jyothi, C. ; Reddy, K. R. Adv. Synth. Catal. 2011, 353, 401.
  (h) Xue, S. ; McKenna, J. ; Shieh, W. C. ; Repic, O. J. Org. Chem. 2004, 69, 6474.
  (i) Chenard, B. L. ; Welch, W. M. ; Blake, J. F. ; Butler, T. W. ; Reinhold, A. ; Ewing, F. E. ; Menniti, F. S. ; Pagnozzi, M. J. J. Med. Chem. 2001, 44, 1710.
  (j) Coppola, G. M. J. Heterocycl. Chem. 1999, 36, 563.
  (k) Larksarp, C. ; Alper, H. Org. Lett. 1999, 1, 1619.
  (l) Kotsuki, H. ; Sakai, H. ; Morimoto, H. ; Suenaga, H. Synlett 1999, 1993.
  (m) Cacchi, S. ; Fabrizi, G. ; Marinelli, F. Synlett 1996, 997.
  (n) Larock, R. C; . Fellows, C. A. J. Org. Chem. 1980, 45, 363.
  (o) Errede, L. A. J. Org. Chem. 1976, 41, 1763.
  (p) Jackson, T. G. ; Morris, S. R. ; Turner, R. H. J. Chem. Soc. 1968, 13, 1592.
  (q) Taylor, E. C. ; Knopf, R. I. ; Borror, A. L. J. Am. Chem. Soc. 1960, 82, 3152.
7. [7]
  For recent examples on the synthesis of 4H-3, 1-benzoxazin-4-ones 3, see: (a) Wang, L. ; Xie, Y. -B; Huang, N. -Y. ; Yan, J. -Y. ; Hu, W. -M. ; Liu, M. -G. ; Ding, M. -W. ACS Catal. 2016, 6, 4010.
  (b) Verma, A. ; Kumar, S. Org. Lett. 2016, 18, 4388.
  (c) Arcadi, A. ; Chiarini, M. ; Vecchio, L. D. ; Marinelli, F. ; Michelet, V. Chem. Commun. 2016, 52, 1458.
  (d) Laha, J. K. ; Patel, K. V. ; Tummalapalli, K. S. S. ; Dayal, N. Chem. Commun. 2016, 52, 10245.
  (e) Prakash, R. ; Gogoi, S. Adv. Synth. Catal. 2016, 19, 3046.
  (f) Yu, J. ; Zhang-Negrerie, D. ; Du, Y. Eur. J. Org. Chem. 2016, 2016, 562.
  (g) Wu, X. F. ; Schranck, J. ; Neumann, H. ; Beller, M. Chem. -Eur. J. 2011, 17, 12246.
  (h) Liu, Q. ; Chen, P. ; Liu, G. ACS Catal. 2013, 3, 178.
  (i) Li, W. ; Wu, X. F. J. Org. Chem. 2014, 79, 10410.
  (j) Chavan, S. P. ; Bhanage, B. M. Eur. J. Org. Chem. 2015, 2015, 2405.
  (k) Munusamy, S. ; Venkatesan, S. ; Sathiyanarayanan, K. I. Tetrahedron Lett. 2015, 56, 203.
  (l) Larksarp, C. ; Alper, H. Org. Lett. 1999, 1, 1619.
  (m) Salvadori, J. ; Balducci, E. ; Zaza, S. ; Petricci, E. ; Taddei, M. J. Org. Chem. 2010, 75, 1841.
  (n) Nayak, M. K. ; Kim, B. H. ; Kwon, J. E. ; Park, S. ; Seo, J. ; Chung, J. W. ; Park, S. Y. Chem. -Eur. J. 2010, 16, 7437.
8. [8]
  For recent selected reviews on gold-catalyzed reactions, see: (a) Harris, R. J. ; Widenhoefer, R. A. Chem. Soc. Rev. 2016, 45, 4533.
  (b) Asiri, A. M. ; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 4471.
  (c) Zheng, Z. ; Wang, Z. ; Wang, Y. ; Zhang, L. Chem. Soc. Rev. 2016, 45, 4448.
  (d) Ziand, W. ; Toste, F. D. Chem. Soc. Rev. 2016, 45, 4567.
  (e) Huple, D. B. ; Ghorpade, S. ; Liu, R. -S. Adv. Synth. Catal. 2016, 358, 1348.
  (f) Dorel, R. ; Echavarren, A. M. Chem. Rev. 2015, 115, 9028.
  (g) Jia, M. ; Bandini, M. ACS Catal. 2015, 5, 1638.
  (h) Wang, Y. ; Muratore, M. E. ; Echavarren, A. M. Chem. Eur. J. 2015, 21, 7332.
  (i) Zhang, L. Acc. Chem. Res. 2014, 47, 877.
  (j) Yeom, H. -S. ; Shin, S. Acc. Chem. Res. 2014, 47, 966.
  (k) Fensterbank, L. ; Malacria, M. Acc. Chem. Res. 2014, 47, 953.
  (l) Benitez, D. ; Shapiro, N. D. ; Tkatchouk, E. ; Wang, Y. ; God-dard Ⅲ, W. A. ; Toste, F. D. Nat. Chem. 2009, 1, 482.
  (m) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
  (n) Wu, W. -T. ; Zhang, L. ; You, S. -L. Acta Chim. Sinica 2017, 75, 419(in Chinese). (吴文挺, 张立明, 化学学报, 2017, 75, 419. )
  for recent selected examples, see: (o) Zhao, J. -R. ; Yuan, X. ; Wang, Z. ; Chen, S. ; Zhang, Z. -X. ; Xue, W. Org. Chem. Front. 2015, 2, 34.
  (p) Li, L. ; Zhou, B. ; Ye, L. Chin. J. Org. Chem. 2015, 35, 655(in Chinese). (李龙, 周波, 叶龙武, 有机化学, 2015, 35, 655. )
  (q) Zhang, P. -C. ; Wang, Y. ; Qian, D. ; Li, W. ; Zhang, J. Chin. J. Chem. 2017, 35, 849.
9. [9]
  For recent selected a review on the generation of α-imino gold carbenes, see: Davies, P. W. ; Garz n, M. Asian J. Org. Chem. 2015, 4, 694.
10. [10]
  For recent selected examples, see: (a) Lonca, G. H. ; Tejo, C. ; Chan, H. L. ; Chiba, S. ; Gagosz, F. Chem. Commun. 2017, 53, 736.
  (b) Jin, H. ; Tian, B. ; Song, X. ; Xie, J. ; Rudolph, M. ; Rominger, F. ; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 12688.
  (c) Pan, Y. ; Chen, G. -W. ; Shen, C. -H. ; He, W. ; Ye, L. -W. Org. Chem. Front. 2016, 3, 391.
  (d) Li, N. ; Lian, X. -L. ; Li, Y. -H. ; Wang, T. -Y. ; Han, Z. -Y. ; Zhang, L. ; Gong, L. -Z. Org. Lett. 2016, 18, 4178.
  (e) Jin, H. ; Huang, L. ; Xie, J. ; Rudolph, M. ; Rominger, F. ; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 794.
  (f) Zhou, A. -H. ; He, Q. ; Shu, C. ; Yu, Y. -F. ; Liu, S. ; Zhao, T. ; Zhang, W. ; Lu, X. ; Ye, L. -W. Chem. Sci. 2015, 6, 1265.
  (g) Xiao, X. -Y. ; Zhou, A. -H. ; Shu, C. ; Pan, F. ; Li, T. ; Ye, L-W. Chem. -Asian J. 2015, 10, 1854.
  (h) Shen, C. -H. ; Pan, Y. ; Yu, Y. -F. ; Wang, Z. -S. ; He, W. ; Li, T. ; Ye, L. -W. J. Organomet. Chem. 2015, 795, 63.
  (i) Li, N. ; Wang, T. -Y. ; Gong, L. -Z; Zhang, L. Chem. -Eur. J. 2015, 21, 3585.
  (j) Shu, C. ; Wang, Y. -H. ; Zhou, B. ; Li, X. -L. ; Ping, Y. -F. ; Lu, X. ; Ye, L. -W. J. Am. Chem. Soc. 2015, 137, 9567.
  (k) Zhu, L. ; Yu, Y. ; Mao, Z. ; Huang, X. Org. Lett. 2015, 17, 30.
  (l) Wu, Y. ; Zhu, L. ; Yu, Y. ; Luo, X. ; Huang, X. J. Org. Chem. 2015, 80, 11407.
  (m) Pawar, S. K. ; Sahani, R. L. ; Liu, R. -S. Chem. -Eur. J. 2015, 21, 10843.
  (n) Prechter, A. ; Henrion, G. ; dit Bel, P. F. ; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959.
  (o) Garzón M. ; Davies, P. W. Org. Lett. 2014, 16, 4850.
  (p) Tokimizu, Y. ; Oishi, S. ; Fujii, N. ; Ohno, H. Org. Lett. 2014, 16, 3138.
  (q) Chatzopoulou, E. ; Davies, P. W. Chem. Commun. 2013, 49, 8617.
  (r) Yan, Z. -Y. ; Xiao, Y. ; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624.
  (s) Xiao, Y. ; Zhang, L. Org. Lett. 2012, 14, 4662.
  (t) Lu, B. ; Luo, Y. ; Liu, L. ; Ye, L. ; Wang, Y. ; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
  (u) Wetzel, A. ; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
  (v) Li, C. ; Zhang, L. Org. Lett. 2011, 13, 1738.
  (w) Davies, P. W. ; Cremones, A. ; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931.
  (x) Gorin, D. J. ; Davis, N. R. ; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
11. [11]
  For our recent studies on gold-catalyzed tandem reactions, see: (a) Chen, C. ; Zou, Y. ; Chen, X. ; Zhang, X. ; Rao, W. ; Chan, P. W. H. Org. Lett. 2016, 18, 4730.
  (b) Zhang, X. ; Sun, X. ; Fan, H. ; Lyu, C. ; Li, P. ; Zhang, H. ; Rao, W. RSC Adv. 2016, 6, 56319.
  (c) Zhang, X. ; Sun, X. ; Fan, H. ; Li, P. ; Lyu, C. ; Rao, W. Eur. J. Org. Chem. 2016, 25, 4265.
  (d) Zhang, X. ; Sun, X. ; Fan, H. ; Cui, X. ; Ma, M. Chin. J. Org. Chem. 2015, 35, 1469(in Chinese). (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469. )
12. [12]
  Wang, J.; Jiang, X.; Zhang, Y.; Zhu, Y.; Shen, J. Tetrahedron Lett. 2015, 56, 2349. doi: 10.1016/j.tetlet.2015.03.121
13. [13]
  Eid, A. I. Eur. J. Med. Chem. 1979, 14, 463.
1. [1]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
2. [2]
  Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
3. [3]
  Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
4. [4]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
5. [5]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
6. [6]
  Xiangdong Lai , Tengfei Liu , Zengchao Guo , Yihan Wang , Jiang Xiao , Qingxiu Xia , Xiaohui Liu , Hui Jiang , Xuemei Wang . In situ formed fluorescent gold nanoclusters inhibit hair follicle regeneration in oxidative stress microenvironment via suppressing NFκB signal pathway. Chinese Chemical Letters, 2025, 36(2): 109762-. doi: 10.1016/j.cclet.2024.109762
7. [7]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
8. [8]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
9. [9]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
10. [10]
  Chuyu Huang , Zhishan Liu , Linping Zhao , Zuxiao Chen , Rongrong Zheng , Xiaona Rao , Yuxuan Wei , Xin Chen , Shiying Li . Metal-coordinated oxidative stress amplifier to suppress tumor growth combined with M2 macrophage elimination. Chinese Chemical Letters, 2024, 35(12): 109696-. doi: 10.1016/j.cclet.2024.109696
11. [11]
  Chen-Chang Cui , Shao-Qing Shi , Lu-Yao Wang , Feng Lin , Man-Su Tu , Wen-Juan Hao , Bo Jiang . Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation. Chinese Chemical Letters, 2025, 36(6): 110541-. doi: 10.1016/j.cclet.2024.110541
12. [12]
  Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH₂-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
13. [13]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
14. [14]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
15. [15]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
16. [16]
  Jijoe Samuel Prabagar , Kumbam Lingeshwar Reddy , Dong-Kwon Lim . Visible-light responsive gold nanoparticle and nano-sized Bi2O3-x sheet heterozygote structure for efficient photocatalytic conversion of N2 to NH3. Chinese Journal of Structural Chemistry, 2025, 44(4): 100564-100564. doi: 10.1016/j.cjsc.2025.100564
17. [17]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
18. [18]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
19. [19]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
20. [20]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(2263)
HTML views(223)

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