Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives

doi:10.6023/cjoc201211037

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 568-572.DOI: 10.6023/cjoc201211037 Previous Articles Next Articles

Articles

基于萘基新型冠醚的合成、晶体结构及其对联吡啶盐的络合性能研究

宗乾收^a,b,c, 吴建一^a,b

a 嘉兴学院生物与化学工程学院嘉兴 314001;
b 嘉兴市化工清洁工艺重点实验室, 浙江嘉兴 314001;
c 浙江大学药学院杭州 310058

收稿日期:2012-11-20 修回日期:2012-12-04 发布日期:2012-12-10
通讯作者: 宗乾收 E-mail:zongqs@iccas.ac.cn
基金资助:
中国博士后科学基金面上基金(No. 2011M500989)、浙江省高校优秀青年教师(No. 00511024)资助项目.

Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives

Zong Qianshou^a,b,c, Wu Jianyi^a,b

a Department of Biology and Chemical Engineering, Jiaxing University, Jiaxing 314001;
b Key Laboratory of Chemical Cleaning Technology, Jiaxing City, Jiaxing 314001;
c School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058

Received:2012-11-20 Revised:2012-12-04 Published:2012-12-10
Supported by:
Project supported by the China Postdoctoral Science Foundation (No. 2011M500989) and the Excellent Yong Teachers Program of Zhejiang Province (No. 00511024).

A Novel naphthalene-based crown ether has been synthesized by the etherification of 2,7-dihydroxynaphthalene with 8-tosyloxy-3,6-dioxaoctanol in the presence of K₂CO₃, followed by reaction with p-toluenesufonyl chloride to give 7. Compound 7 was further reacted with 2,7-dihydroxynaphthalene in the presence of cesium carbonate to give 1 in 38% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic, space group P-1 with a＝ 8.165(3) Å, b＝13.435(4) Å, c＝14.083(3) Å, α＝64.11(2)°, β＝80.40(3)°, γ＝88.19(3)°, V＝1368.9(7) Å³, Z＝2, D_c＝1.331 g/cm³, λ＝0.071070 nm, μ(Mo Kα)＝1.331 mm^-1, M_r＝353.22, F(000)＝584. The crystal structure of 1 shows that two napthalene units are linked two tri(ethylene glycol) bridges to form dinapthalzo[30]crown-8 cavity and one Z-like central cavity with size of ca. 8.2 Å×12.0 Å. The host 4 was proved to be a efficient host for the complexation with paraquat derivatives in solution by ¹H NMR.

Key words: crown ethers, synthesis, crystal structure, complexation, paraquat derivatives

Cite this article

Zong Qianshou, Wu Jianyi. Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives[J]. Chin. J. Org. Chem., 2013, 33(03): 568-572.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
(b) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017.

[2] Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry, Nankai University Publication, Tianjin, 2001 (in Chinese).
(刘育, 尤长城, 张衡益, 超分子化学, 南开大学出版社, 天津, 2001.)

[3] (a) Zong, Q. S.; Chen, C. F. Org. Lett. 2006, 8, 211.
(b) Zong, Q. S.; Zhang, C.; Chen, C. F. Org. Lett. 2006, 8, 1859.
(c) Han, Y.; Lu, H. Y.; Zong, Q. S.; Guo, J. B.; Chen, C. F. J. Org. Chem. 2012, 77, 2422.
(d) Zhao, J. M.; Zong, Q. S.; Chen, C. F. J. Org. Chem. 2010, 75, 5092.
(e) Su, Y. S.; Chen, C. F. Org. Lett. 2010, 12, 1888.

[4] Tang, C. C.; Wang, L. H.; Yun, Y. B.; Zhang, C. L.; Liu, B. Q. Acta Chim. Sinica 2011, 69, 343 (in Chinese).
(唐橙橙, 王丽华, 贠延滨, 张陈淋, 刘必前, 化学学报, 2011, 69, 343.)

[5] Zhang, Q.; Xu, J. Acta Chim. Sinica 2011, 69, 2287 (in Chinese).
(张强, 许娟, 化学学报, 2011, 69, 2287.)

[6] Ye, Q. J.; Yang, F. F.; Zhang, Y. Y.; Jiao, Z. Y.; Guo, H. Y. Chin. J. Org. Chem. 2012, 32, 189 (in Chinese).
(叶进启, 杨发福, 张筱逸, 焦自玉, 郭红玉, 有机化学, 2012, 32, 189.)

[7] (a) Huang, F. H.; Zakharov, L. N.; Rheingold, A. L.; Ashraf-Khorassani, M.; Gibson, H. W. J. Org. Chem. 2005, 70, 809.
(b) Huang, F. H.; Gibson, H. W.; Bryant, W. S.; Nagvekar, D. S.; Fronczek, F. R. J. Am. Chem. Soc. 2003, 125, 9367.
(c) Pederson, A. M. P.; Ward, E.; Schoonover, D. S.; Slebodnick, C.; Gibson, H. W. J. Org. Chem. 2008, 73, 9094.
(d) Zhang, M. M.; Zhu, K. L.; Huang, F. H. Chem. Commun. 2010, 46, 8131.
(e) Zhang, M. M.; Zheng, B.; Huang, F. H. Chem. Commun. 2011, 47, 10103.

[8] (a) Chen, L.; Zhang, Y. M.; Liu, Y. J. Phys. Chem. B 2012, 116, 9500.
(b) Chen, L.; Zhang H. Y.; Liu Y. J. Org. Chem. 2012, 77, 9766.

[9] (a) Sauvage, J. P.; Dietrich-Buchecker, C. Molecular Catenanes, Eds.: Rotaxanes and Knots, Wiley-VCH, Weinheim, Germany, 1999.
(b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
(c) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348.

[10] (a) Suresh, M.; Mandal, A. K.; Kesharwani, M. K.; Adarsh, N. N.; Ganguly, B.; Kanaparthi, R. K.; Samanta, A.; Das, A. J. Org. Chem. 2011, 76, 138.
(b) Mandal, A. K.; Das, P.; Mahato, P.; Acharya, S.; Das, A. J. Org. Chem. 2012, 77, 6789.
(c) Davidson, G. J. E.; Sharma, S.; Loeb, S. J. Angew. Chem., Int. Ed. 2010, 49, 4938.
(d) Hubbard, A. L.; Davidson, G. J. E.; Patel, R. H.; Wisner, J. A.; Loeb, S. J. Chem. Commun. 2004, 39, 138.

[11] Zong, Q. S.; Wu, J. Y. Chin. J. Org. Chem. 2012, 32, 1509 (in Chinese).
(宗乾收, 吴建一, 有机化学, 2012, 32, 1509.)

[12] Boerjesson, L.; Welch, C. J. Acta Chem. Scand. 1991, 45, 621.

[13] Sheldrick, G. M. SHELXS97, A Program for Automatic Solution of Crystal Structure, University of Göttingen, Germany, 1997.

[14] Sheldrick, G. M. SHELXS97, A Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
[15]Connors, K. A. Binding Constants, J. Wiley and Sons, New York, 1987.

基于萘基新型冠醚的合成、晶体结构及其对联吡啶盐的络合性能研究

Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.