5-ethyl-7,10-dihydroxy-1,2,3,4-tetrahydrobenzo[f]quinoxalin-6(10bH)-one | 1184950-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-ethyl-7,10-dihydroxy-1,2,3,4-tetrahydrobenzo[f]quinoxalin-6(10bH)-one
• CAS: 1184950-96-6
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: ISWPINLFDPNYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.92
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-ethyl-5,7,8-trihydroxynaphthalene-1,4-dione 、 1,2-diaminoethane dihydrochloride 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 以85%的产率得到5-ethyl-7,10-dihydroxy-1,2,3,4-tetrahydrobenzo[f]quinoxalin-6(10bH)-one
  参考文献：
  名称：

  Amination of 2-hydroxy- and 2,3-dihydroxynaphthazarins. Synthesis of echinamines A and B, metabolites produced by the sand dollar Scaphechinus mirabilis

  摘要：

  2-Hydroxynaphthazarins reacted with aqueous ammonia at the C(1)=O carbonyl group, following the addition-elimination pattern with formation of 8-aminojuglone derivatives. Reactions of 2,3-dihydroxynaphthazarins with the same reagent involved the C(2)=O carbonyl group of the corresponding 1,2-naphthoquinoid tautomer to produce 2-aminonaphthazarin derivatives. 7-Ethyl-2,3,6-trihydroxynaphthazarin (echinochrome) reacted with aqueous ammonia to give 3(2)-amino-7-ethyl-2(3),6-dihydroxynaphthazarins (echinamines A and B) that are metabolites recently isolated from the sand dollar Scaphechinus mirabilis.

  DOI：

  10.1134/s1070428009010060