1-羟基-2-羧基蒽醌 | 7400-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-羟基-2-羧基蒽醌
• 英文名称: 1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• 英文别名: 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid；2-carboxy-1-hydroxyanthraquinone；1-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid；1-Hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure；1-Oxy-anthrachinon-carbonsaeure-(2)；1-Hydroxy-2-carboxyanthrachinon
• CAS: 7400-93-3
• 化学式: C₁₅H₈O₅
• 分子量: 268.226
• InChiKey: KUNHZSKWJIXMCA-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C
• 沸点：
  519.0±50.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-羟基-2-羧基蒽醌 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 62.83h， 生成 N-[3-(dimethylamino)propyl]-1-hydroxy-9,10-dioxoanthracene-2-carboxamide
  参考文献：
  名称：

  Preparation and evaluation of 2-substituted anthraquinones based on the anthracyclines

  摘要：

  Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated. All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds. Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.

  DOI：

  10.1021/jm00346a008
• 作为产物：
  描述：

  1-氨基蒽醌-2-羧酸 在 硫酸 、 水 、 sodium nitrite 作用下， 生成 1-羟基-2-羧基蒽醌
  参考文献：
  名称：

  Preparation and evaluation of 2-substituted anthraquinones based on the anthracyclines

  摘要：

  Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated. All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds. Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.

  DOI：

  10.1021/jm00346a008

文献信息

• Scholl, Monatshefte fur Chemie, 1913, vol. 34, p. 1016 Anm. 2
  作者：Scholl

  DOI：——

  日期：——
• DE383030
  申请人：——

  公开号：——

  公开（公告）日：——
• Boddy, Ian K.; Cambie, Richard C.; Rutledge, Peter S., Australian Journal of Chemistry, 1986, vol. 39, p. 2075 - 2088
  作者：Boddy, Ian K.、Cambie, Richard C.、Rutledge, Peter S.、Woodgate, Paul D.

  DOI：——

  日期：——
• Charcharow, 1934, vol. 4, p. 268,271
  作者：Charcharow

  DOI：——

  日期：——
• Ioffe; Schtokgammer, 1937, vol. 4, p. 257,259
  作者：Ioffe、Schtokgammer

  DOI：——

  日期：——