4-ethyl-6,9-dihydroxy-2,2-dimethylnaphtho[1,2-d]oxazol-5(2H)-one | 1184950-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-ethyl-6,9-dihydroxy-2,2-dimethylnaphtho[1,2-d]oxazol-5(2H)-one
• CAS: 1184950-94-4
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: RREGCEIPAVBSJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.12
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  8-amino-6-ethyl-5,7-dihydroxy-1,4-dihydronaphthalene-1,4-dione 在 硫酸 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以95%的产率得到4-ethyl-6,9-dihydroxy-2,2-dimethylnaphtho[1,2-d]oxazol-5(2H)-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

文献信息

• Amination of 2-hydroxy- and 2,3-dihydroxynaphthazarins. Synthesis of echinamines A and B, metabolites produced by the sand dollar Scaphechinus mirabilis
  作者：G. I. Mel’man (Sopel’nyak)、N. P. Mishchenko、V. A. Denisenko、D. V. Berdyshev、V. P. Glazunov、V. F. Anufriev

  DOI：10.1134/s1070428009010060

  日期：2009.1

  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.