4-chloro-2,5-dihydroxy-6,11-dioxo-6,11-dihydroanthra[1,2-b]furan-3-carboxylic acid | 1443209-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-chloro-2,5-dihydroxy-6,11-dioxo-6,11-dihydroanthra[1,2-b]furan-3-carboxylic acid
• CAS: 1443209-58-2
• 化学式: C₁₉H₁₁ClO₇
• 分子量: 386.745
• InChiKey: IBJJXLWDVYKJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-chloro-2,5-dihydroxy-6,11-dioxo-6,11-dihydroanthra[1,2-b]furan-3-carboxylic acid 在 硫酸 作用下， 反应 0.5h， 以85%的产率得到2-carboxymethyl-3-chloro-1,4-dihydroxyanthraquinone
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione

  摘要：

  A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-halo-anthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

  DOI：

  10.1007/s10593-013-1240-2
• 作为产物：
  描述：

  2,3-二氯-1,4-二羟基蒽-9,10-二酮 、 丙二酸二乙酯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以88%的产率得到4-chloro-2,5-dihydroxy-6,11-dioxo-6,11-dihydroanthra[1,2-b]furan-3-carboxylic acid
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione

  摘要：

  A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-halo-anthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

  DOI：

  10.1007/s10593-013-1240-2