1-Phenylethynylanthraquinone-2-carboxylic acid | 146135-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Phenylethynylanthraquinone-2-carboxylic acid
• 英文别名: 9,10-dioxo-1-(2-phenylethynyl)anthracene-2-carboxylic acid
• CAS: 146135-86-6
• 化学式: C₂₃H₁₂O₄
• 分子量: 352.346
• InChiKey: UWUNWXUNQWSGHB-UHFFFAOYSA-N

物化性质

• 沸点：
  640.0±55.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Phenylethynylanthraquinone-2-carboxylic acid 在 吡啶 、 copper(I) phenylacetylenide 作用下， 反应 2.5h， 以79.5%的产率得到4H-2-phenylanthra<2,1-c>pyran-4,7,12-trione
  参考文献：
  名称：

  Cyclization of acetylenic derivatives of aromatic carboxylic acids

  摘要：

  The Cu(I)-catalyzed intramolecular cyclization of 1-phenylethynyl-and 1-hexyn-1-yl-anthraquinone-2-carboxylic acid is a 6-endo-dig-addition, whereas the reaction for 1-(3-phenoxypropyn-1-yl)anthraquinone-2-carboxylic acid proceeds in a directionally nonspecific way. It is shown that the cyclization of vicinal acetylenic derivatives of aromatic carboxylic acids leads to the formation of the more stable of the possible cyclic, structures.

  DOI：

  10.1007/bf00863591
• 作为产物：
  描述：

  1-iodoanthraquinone-2-carboxylic acid 在 吡啶 、 氢氧化钾 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 44.0h， 生成 1-Phenylethynylanthraquinone-2-carboxylic acid
  参考文献：
  名称：

  Cyclization of acetylenic derivatives of aromatic carboxylic acids

  摘要：

  The Cu(I)-catalyzed intramolecular cyclization of 1-phenylethynyl-and 1-hexyn-1-yl-anthraquinone-2-carboxylic acid is a 6-endo-dig-addition, whereas the reaction for 1-(3-phenoxypropyn-1-yl)anthraquinone-2-carboxylic acid proceeds in a directionally nonspecific way. It is shown that the cyclization of vicinal acetylenic derivatives of aromatic carboxylic acids leads to the formation of the more stable of the possible cyclic, structures.

  DOI：

  10.1007/bf00863591

文献信息

• Cyclization of acetylenic derivatives of aromatic carboxylic acids
  作者：I. D. Ivanchikova、G. �. Usubalieva、P. V. Schastnev、A. A. Moroz、M. S. Shvartsberg

  DOI：10.1007/bf00863591

  日期：1992.9

  The Cu(I)-catalyzed intramolecular cyclization of 1-phenylethynyl-and 1-hexyn-1-yl-anthraquinone-2-carboxylic acid is a 6-endo-dig-addition, whereas the reaction for 1-(3-phenoxypropyn-1-yl)anthraquinone-2-carboxylic acid proceeds in a directionally nonspecific way. It is shown that the cyclization of vicinal acetylenic derivatives of aromatic carboxylic acids leads to the formation of the more stable of the possible cyclic, structures.