| Conformation of α,α,α′-Trisubstituted Cyclododecanone |
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| 引用本文： | 王明安,张宁,路慧哲,王道全.Conformation of α,α,α′-Trisubstituted Cyclododecanone[J].中国化学,2007,25(8):1196-1201. |
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| 作者姓名： | 王明安 张宁 路慧哲 王道全 |
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| 作者单位： | Department of Applied Chemistry, China Agricultural University, Beijing 100094, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （No. 20072053） and the Research Foundation of China Agricultural University （No. 2005011）. |
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| 摘 要： | Ten α,α,α′-trisubstituted cyclododecanones were synthesized and characterized by elemental analyses, infrared, 1^H NMR and 13^C NMR spectra, and X-ray diffraction. NMR data could not give conformational information clearly, but some of their ring skeleton conformations of cyclododecanone moiety were showed to remain the unchanged 3333]-2-one conformation with little distortion, while the others were changed to the 3324]-2-one conformation in their crystal structures. These are consistent with the results of molecular mechanics calculation with Sybyl 6.9 software and Tripos force field, and semi-empirical quantum calculation with AM 1 method in Gaussian 98 software. Two geminal substituting groups are located at α-corner carbon atom, and the third group is at α-side-exo carbon atom in both conformations. Both 3333]-2-one and 3324]-2-one conformations are present in a dynamic equilibrium in the solution, but only one preferred conformation exists in the crystal solid.
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| 关 键 词： | -2-酮 构象 结构分析 α α α′-环十二酮 抑制剂 化学性质 |
| 修稿时间： | 2006-09-072007-04-09 |
Conformation of α,α,α′-Trisubstituted Cyclododecanone |
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| WANG Ming-An,ZHANG Ning,LU Hui-Zhe,WANG Dao-Quan.Conformation of α,α,α′-Trisubstituted Cyclododecanone[J].Chinese Journal of Chemistry,2007,25(8):1196-1201. |
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| Authors: | WANG Ming-An ZHANG Ning LU Hui-Zhe WANG Dao-Quan |
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| Institution: | Department of Applied Chemistry, China Agricultural University, Beijing 100094, China |
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| Abstract: | Ten α,α,α′‐trisubstituted cyclododecanones were synthesized and characterized by elemental analyses, infrared, 1H NMR and 13C NMR spectra, and X‐ray diffraction. NMR data could not give conformational information clearly, but some of their ring skeleton conformations of cyclododecanone moiety were showed to remain the unchanged 3333]‐2‐one conformation with little distortion, while the others were changed to the 3324]‐2‐one conformation in their crystal structures. These are consistent with the results of molecular mechanics calculation with Sybyl 6.9 software and Tripos force field, and semi‐empirical quantum calculation with AM1 method in Gaussian 98 software. Two geminal substituting groups are located at α‐corner carbon atom, and the third group is at α‐side‐exo carbon atom in both conformations. Both 3333]‐2‐one and 3324]‐2‐one conformations are present in a dynamic equilibrium in the solution, but only one preferred conformation exists in the crystal solid. |
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| Keywords: | α α α′trisubstituted cyclododecanone conformation -2-one -2-one |
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