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



宗乾收a,b,c, 吴建一a,b   

  1. 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
  • 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 Qianshoua,b,c, Wu Jianyia,b   

  1. 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, Dc=1.331 g/cm3, λ=0.071070 nm, μ(Mo Kα)=1.331 mm-1, Mr353.22, 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