2-thiatricyclo<3.3.1.1^3,7>decan-4-one | 36223-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 2-thiatricyclo<3.3.1.1^3,7>decan-4-one
• 英文别名: 2-Thiaadamantan-4-on；2-thia-adamantan-4-one；2-Thiaadamantan-4-one；2-thiatricyclo[3.3.1.13,7]decan-4-one
• CAS: 36223-95-7
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: PHRHIGFHKPECKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-thiatricyclo<3.3.1.1^3,7>decan-4-one 在 间氯过氧苯甲酸 作用下， 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  The determination of sulfoxide configuration in six-membered rings using NMR spectroscopy and DFT calculations

  摘要：

  Cyclic six-membered ring sulfoxides and sulfones were prepared by a stepwise in situ oxidation of the corresponding sulfides with meta-chloroperbenzoic acid in an NMR tube. The oxidation was followed by NMR spectra and the H-1 and C-13 NMR data were collected. The geometries of all of the compounds were optimized using the DFT B3LYP/6-31G** method and the C-13 and H-1 NMR chemical shifts were calculated for geometry-optimized structures with the DFT B3LYP/6-31++G** method. The calculated C-13 NMR chemical shifts induced by oxidation (Delta delta values) are in very good agreement with the experimental data and can be used to determine the oxidation state of the sulfur atom (-S-, -SO-, -SO2-). The characteristic differences of the induced oxidation chemical shifts of carbon atoms at the alpha- and beta-position to sulfur were successfully used for distinguishing between the diastereoisomeric sulfoxides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.001

文献信息

• The determination of sulfoxide configuration in six-membered rings using NMR spectroscopy and DFT calculations
  作者：M. Dračínský、R. Pohl、L. Slavětínská、J. Janků、M. Buděšínský

  DOI：10.1016/j.tetasy.2011.02.001

  日期：2011.2

  Cyclic six-membered ring sulfoxides and sulfones were prepared by a stepwise in situ oxidation of the corresponding sulfides with meta-chloroperbenzoic acid in an NMR tube. The oxidation was followed by NMR spectra and the H-1 and C-13 NMR data were collected. The geometries of all of the compounds were optimized using the DFT B3LYP/6-31G** method and the C-13 and H-1 NMR chemical shifts were calculated for geometry-optimized structures with the DFT B3LYP/6-31++G** method. The calculated C-13 NMR chemical shifts induced by oxidation (Delta delta values) are in very good agreement with the experimental data and can be used to determine the oxidation state of the sulfur atom (-S-, -SO-, -SO2-). The characteristic differences of the induced oxidation chemical shifts of carbon atoms at the alpha- and beta-position to sulfur were successfully used for distinguishing between the diastereoisomeric sulfoxides. (C) 2011 Elsevier Ltd. All rights reserved.