1-(2,6-dibromophenyl)-2,2-dimethylpropan-1-one | 934334-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,6-dibromophenyl)-2,2-dimethylpropan-1-one
• CAS: 934334-04-0
• 化学式: C₁₁H₁₂Br₂O
• 分子量: 320.024
• InChiKey: NIXCCTZDEPCFCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,6-dibromophenyl)-2,2-dimethylpropan-1-one 、 3-异丙基苯硼酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 生成 1-[2',6'-bis(3-isopropylphenyl)phenyl]-2,2-dimethylpropan-1-one 、 1-[2'-(3-isopropylphenyl)-6'-phenylphenyl]-2,2-dimethylpropan-1-one
  参考文献：
  名称：

  Conformational Consequences of the Dynamic Processes in the Stereolabile Atropisomers of Acyl-Substituted m-Terphenyl Derivatives

  摘要：

  By means of low-temperature NMR spectroscopy, conformers (stereolabile atropisomers) due to the restricted rotation about the Ar-Ar and Ar-C(O) R bonds were detected in a number of acylphenyl derivatives, substituted in positions 2 and 6 by the 3-isopropylphenyl moiety (compounds 1-3, R = H, Me, and t-Bu, respectively). The conformational assignment was accomplished on the basis of the symmetry of the low-temperature C-13 NMR spectra with the added support of ab initio calculations. The interconversion barriers were also determined by complete line shape simulation of the NMR spectra, and the experimental values were satisfactorily reproduced by ab initio calculations. In the case of the asymmetric derivative 4, two enantiomers, generated by the restricted t-BuC(O)-Ar rotation, were found sufficiently stable to allow their separation by means of the enantioselective HPLC technique at ambient temperature and to obtain the corresponding CD spectra.

  DOI：

  10.1021/jo062558g
• 作为产物：
  描述：

  特戊醛 在 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2,6-dibromophenyl)-2,2-dimethylpropan-1-one
  参考文献：
  名称：

  Conformational Consequences of the Dynamic Processes in the Stereolabile Atropisomers of Acyl-Substituted m-Terphenyl Derivatives

  摘要：

  By means of low-temperature NMR spectroscopy, conformers (stereolabile atropisomers) due to the restricted rotation about the Ar-Ar and Ar-C(O) R bonds were detected in a number of acylphenyl derivatives, substituted in positions 2 and 6 by the 3-isopropylphenyl moiety (compounds 1-3, R = H, Me, and t-Bu, respectively). The conformational assignment was accomplished on the basis of the symmetry of the low-temperature C-13 NMR spectra with the added support of ab initio calculations. The interconversion barriers were also determined by complete line shape simulation of the NMR spectra, and the experimental values were satisfactorily reproduced by ab initio calculations. In the case of the asymmetric derivative 4, two enantiomers, generated by the restricted t-BuC(O)-Ar rotation, were found sufficiently stable to allow their separation by means of the enantioselective HPLC technique at ambient temperature and to obtain the corresponding CD spectra.

  DOI：

  10.1021/jo062558g