ethyl 5-hydroxy-4,7-dioxobenzothiophene-6-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-hydroxy-4,7-dioxobenzothiophene-6-carboxylate
• 英文别名: Ethyl 5-hydroxy-4,7-dioxo-benzothiophene-6-carboxylate；ethyl 5-hydroxy-4,7-dioxo-1-benzothiophene-6-carboxylate
• 化学式: C₁₁H₈O₅S
• 分子量: 252.248
• InChiKey: PYQXPAIMSTWCEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-4,7-dioxobenzothiophene-6-carboxylate 在 盐酸 、 sodium hydroxide 作用下， 生成 5-hydroxy-4,7-dioxobenzothiophene
  参考文献：
  名称：

  Friedel-Crafts coordinated processes: highly selective synthesis of hydroxynaphthoquinones

  摘要：

  Simple preparation of ethyl 3-hydroxy-1,4-naphthoquinone-2-carboxylates 2 including heterocyclic analogs is accomplished by C-regioselective bis-acylation of aromatic and heteroaromatic beta-keto esters 1. Compounds 2 are readily hydrolyzed and decarboxylated to the corresponding 2-hydroxy-1,4-naphthoquinone derivatives 3.

  DOI：

  10.1021/jo00056a014
• 作为产物：
  描述：

  草酰氯 、 2-噻吩甲酰乙酸乙酯 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以85%的产率得到ethyl 5-hydroxy-4,7-dioxobenzothiophene-6-carboxylate
  参考文献：
  名称：

  Friedel-Crafts coordinated processes: highly selective synthesis of hydroxynaphthoquinones

  摘要：

  Simple preparation of ethyl 3-hydroxy-1,4-naphthoquinone-2-carboxylates 2 including heterocyclic analogs is accomplished by C-regioselective bis-acylation of aromatic and heteroaromatic beta-keto esters 1. Compounds 2 are readily hydrolyzed and decarboxylated to the corresponding 2-hydroxy-1,4-naphthoquinone derivatives 3.

  DOI：

  10.1021/jo00056a014