Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1509-1512.DOI: 10.6023/cjoc201204006 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 嘉兴 314001;
    c 浙江大学药学院 杭州 310058
  • 收稿日期:2012-04-05 修回日期:2012-04-25 发布日期:2012-05-04
  • 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 Open Chain Crown Ether: Synthesis and Crystal Structure

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 of Jiaxing City, Jiaxing 314001;
    c School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058
  • Received:2012-04-05 Revised:2012-04-25 Published:2012-05-04
  • 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 open-chain crown ether has been synthesized by the etherification of 2-bromo- N-phenylacetamide with 3,6-dibromo-2,7-dihydroxynaphthalene, followed by reduction with sodium borohydride and boron trifluoride ether solution, in 95% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic space group P-1 with a=9.588(3) Å, b=10.898(3) Å, c=13.060(4) Å, α=103.190(4)°, β=93.953(4)°, γ=115.622(5)°, V=1176.0(6) Å3, Z=2, Dc=1.571 g/cm3, λ=0.71075 Å, μ(Mo Kα)=3.472 mm-1, Mr=353.22 and F(000)=560. In the structure, one of the N—H groups forms bifurcated N—H…Br and N—H…O hydrogen bonds. These link the molecules into inversion related dimers. The centrosymmetric dimers are aggregated via pairs of C—H…π interactions into two-dimensional sheets parallel to (110).

Key words: open-chain crown ethers, synthesis, crystal structure