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

doi:10.6023/cjoc201211037

有机化学 ›› 2013, Vol. 33 ›› Issue (03): 568-572.DOI: 10.6023/cjoc201211037 上一篇下一篇

研究论文

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).

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摘要/Abstract

以2,7-二羟基萘为起始原料, 经与8-(对甲苯磺酰氧基)-3,6-二氧-1-辛醇醚化, 再与对甲苯磺酰氯酯化得7, 7最后与2,7-二羟基萘在碳酸铯为碱作用下得基于2,7-二羟基萘基块新型的冠醚, 三步总收率为35%. 利用单晶X衍射研究其结构, 晶体为三斜晶系, P-1空间群, a＝8.165(3) Å, b＝13.435(4) Å, c＝14.083(3) Å, γ＝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. 在1的晶体结构中, 两个萘基块通过二缩三乙二醇醚键相连形成1个二萘并[30]-冠-8大环结构, 空腔大小为8.2 Å×12.0 Å, 分子呈Z型结构. 通过核磁研究了主体分子1对联吡啶盐在溶液中的相互络合作用.

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

引用此文

宗乾收, 吴建一. 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[J]. 有机化学, 2013, 33(03): 568-572.

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.

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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

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