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有机化学 ›› 2010, Vol. 30 ›› Issue (11): 1700-1704. 上一篇    下一篇

研究论文

cis-2,12-二取代环十二酮的合成及晶体结构

张春艳，陈守聪，刘吉平，王道全，王明安*   

  1. (中国农业大学应用化学系 北京 100193)
  • 收稿日期:2009-12-24 修回日期:2010-05-07 发布日期:2010-06-18
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn, wangmingan2003@yahoo.com
  • 基金资助:

    国家自然科学基金

Synthesis and Crystal Structures of cis-2,12-Bissubstituted Cyclododecanone

ZHANG Chun-Yan, CHEN Shou-Cong, LIU Ji-Ping, WANG Dao-Quan, WANG Ming-An   

  1. (Department of Applied Chemistry, China Agricultural University, Beijing 100193)
  • Received:2009-12-24 Revised:2010-05-07 Published:2010-06-18

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以环十二酮为原料合成了cis-2-苯磺酰基-12-苄基环十二酮、2-苯磺酰基-12-溴代环十二酮和2,12-二苄基环十二酮, 它们的结构通过1H NMR, 13C NMR和元素分析表征. 化合物4的晶体结构参数: C25H32O3S, Mr＝412.57, 三斜晶系, 空间群P1, a＝0.96531(4) nm, b＝1.12703(5) nm, c＝1.17486(5) nm, α＝89.278(2)°, β＝75.582(2)°, γ＝65.385(2)°, V＝1.11938(8) nm3, Dc＝1.224 g/cm3, Z＝2, F(000)＝444, μ(Mo Kα)＝0.167 mm－1, S＝1.038. 化合物6的晶体结构参数: C18H25BrO3S, Mr＝401.35, 三斜晶系, 空间群P1, a＝0.77771(16) nm, b＝1.0143(2) nm, c＝1.2040(2) nm, α＝89.46(3)°, β＝80.13(3)°, γ＝75.27(3)°, V＝0.9044(3) nm3, Dc＝1.474 g/cm3, Z＝2, F(000)＝416和μ(Mo Kα)＝2.400 mm－1, S＝1.042. cis-2-苯磺酰基-12-苄基环十二酮和cis-2-苯磺酰基-12-溴代环十二酮的X射线衍射结果表明, 环十二酮母体骨架采取[3333]-2-酮构象, 较小的取代基位于角顺位, 较大的取代基位于边外向位.

关键词: cis-2,12-二取代环十二酮, α-角顺-α -边外-二取代[3333]-2-酮构象, 优势构象, 晶体结构

cis-2-Phenylsulfonyl-12-benzylcyclododecanone, 2-phenylsulfonyl-12-bromocyclododecanone and 2,12-dibenzylcyclododecanone were synthesized though cyclododecanone as raw material, and their structures were confirmed by 1H NMR, 13C NMR spectra and elemental analysis. Crystal data for 4: C25H32O3S, Mr＝412.57, triclinic, space group P1, a＝0.96531(4) nm, b＝1.12703(5) nm, c＝1.17486(5) nm, α＝89.278(2)°, β＝75.582(2)°, γ＝65.385(2)°, V＝1.11938(8) nm3, Dc＝1.224 g/cm3, Z＝2, F(000)＝444 and m(Mo Kα)＝0.167 mm－1, S＝1.038. Crystal data for 6: C18H25BrO3S, Mr＝401.35, triclinic, space group P1, a＝0.77771(16) nm, b＝1.0143(2) nm, c＝1.2040(2) nm, α＝89.46(3)°, β＝80.13(3)°, γ＝75.27(3)°, V＝0.9044(3) nm3, Dc＝1.474 g/cm3, Z＝2, F(000)＝416 and μ(Mo Kα)＝2.400 mm－1, S＝1.042. The X-ray diffraction analysis of cis-2-phenylsulfonyl-12-benzylcyclododecanone and cis-2-phenylsulfonyl-12-bromocyclododecanone showed that their ring skeleton of cyclododecanone moiety took [3333]-2-one conformation, the smaller substituted group was at α-corner-syn, and the bigger one was at α-side-exo position.

Key words: cis-2,12-bissubstituted cyclododecanone, α-corner-syn-&alpha, -side-exo-bissubstituted[3333]-2-one conformation, preferred conformation, crystal structure