methyl 2-(3-bromo-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate | 1443209-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methyl 2-(3-bromo-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate
• 英文别名: methyl 2-(3-bromo-1,4-dimethoxy-9,10-dioxoanthracen-2-yl)acetate
• CAS: 1443209-64-0
• 化学式: C₁₉H₁₅BrO₆
• 分子量: 419.228
• InChiKey: BSBVBZCMWFXPTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-bromo-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate 在 盐酸 、 copper(l) iodide 、 水 、 铜 、 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 溶剂黄146 、 mineral oil 为溶剂， 反应 11.0h， 生成 4,11-dimethoxy-5,10-dioxo-5,10-dihydroanthra[2,3-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
• 作为产物：
  描述：

  methyl 2-(3-bromo-1,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以57%的产率得到methyl 2-(3-bromo-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate
  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