4-phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid | 102160-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
• 英文别名: 4-anilino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid；4-Anilino-9,10-dioxo-9,10-dihydro-anthracen-2-sulfonsaeure；9,10-Dioxo-4-(Phenylamino)-9,10-Dihydroanthracene-2-Sulfonic Acid；4-anilino-9,10-dioxoanthracene-2-sulfonic acid
• CAS: 102160-11-2
• 化学式: C₂₀H₁₃NO₅S
• 分子量: 379.393
• InChiKey: AAKZMFOUEBXRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  acid blue 25 在 盐酸 、 水 、 sodium nitrite 、 乙醇 、 锌 作用下， 反应 0.01h， 以79%的产率得到4-phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
  参考文献：
  名称：

  Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

  摘要：

  A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.011

文献信息

• 15. The action of bases on 1-diazoanthraquinone-2-sulphonate and its derivatives
  作者：J. I. Lynas-Gray、J. L. Simonsen

  DOI：10.1039/jr9430000045

  日期：——
• Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity
  作者：Younis Baqi、Christa E. Müller

  DOI：10.1016/j.tetlet.2012.09.011

  日期：2012.12

  A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases. (C) 2012 Elsevier Ltd. All rights reserved.