1-(2-methylnaphthyl)anthraquinone | 1094517-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(2-methylnaphthyl)anthraquinone
• 英文别名: 1-(2-Methylnaphthalen-1-yl)anthracene-9,10-dione
• CAS: 1094517-78-8；1094213-23-6
• 化学式: C₂₅H₁₆O₂
• 分子量: 348.401
• InChiKey: XZCVFLRUFXARGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氯蒽醌 、 2-甲基萘-1-硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 苯 为溶剂， 生成 1-(2-methylnaphthyl)anthraquinone
  参考文献：
  名称：

  Structure, Stereodynamics and Absolute Configuration of the Atropisomers of Hindered Arylanthraquinones

  摘要：

  Anthraquinone substituted by 2-methyl-1-naphthyl groups in positions 1,8 yields syn (meso) and anti (racemic) isomers (red and yellow colored, respectively) that interconvert with a barrier of 35.4 kcal mol(-1) in solution. Their structures were identified by NOE experiments in solution and X-ray diffraction in the solids. The racemic anti form (C-2 point group) entails two atropisomers that were separated by enantioselective HPLC: the absolute configuration was assigned by TD-DFT simulation of the ECD spectrum. Two atropisomers were also separated and assigned in the case of anthraquinone bearing a single 2-methyl-1-naphthyl substituent in position 1.

  DOI：

  10.1021/jo802383s

文献信息

• Structure, Stereodynamics and Absolute Configuration of the Atropisomers of Hindered Arylanthraquinones
  作者：Lodovico Lunazzi、Michele Mancinelli、Andrea Mazzanti

  DOI：10.1021/jo802383s

  日期：2009.2.6

  Anthraquinone substituted by 2-methyl-1-naphthyl groups in positions 1,8 yields syn (meso) and anti (racemic) isomers (red and yellow colored, respectively) that interconvert with a barrier of 35.4 kcal mol(-1) in solution. Their structures were identified by NOE experiments in solution and X-ray diffraction in the solids. The racemic anti form (C-2 point group) entails two atropisomers that were separated by enantioselective HPLC: the absolute configuration was assigned by TD-DFT simulation of the ECD spectrum. Two atropisomers were also separated and assigned in the case of anthraquinone bearing a single 2-methyl-1-naphthyl substituent in position 1.