2-azido-3-chloro-7-ethyl-5,6,8-trihydroxynaphthalene-1,4-dione | 880154-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-azido-3-chloro-7-ethyl-5,6,8-trihydroxynaphthalene-1,4-dione
• CAS: 880154-54-1
• 化学式: C₁₂H₈ClN₃O₅
• 分子量: 309.666
• InChiKey: BDJIWWCNZZQPBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  143.59
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-azido-3-chloro-7-ethyl-5,6,8-trihydroxynaphthalene-1,4-dione 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 5,8-dihydroxy-2,6-dimethoxy-3-chloro-7-ethyl-1,4-naphthoquinone
  参考文献：
  名称：

  Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis

  摘要：

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.109
• 作为产物：
  描述：

  2,3-dichloro-7-ethyl-6-hydroxynaphthazarin 在 sodium azide 作用下， 以 甲醇 为溶剂， 生成 2-azido-3-chloro-7-ethyl-5,6,8-trihydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis

  摘要：

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.109

文献信息

• Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis
  作者：Nataly D. Pokhilo、Alla Ya. Yakubovskaya、Vladimir A. Denisenko、Victor Ph. Anufriev

  DOI：10.1016/j.tetlet.2005.12.109

  日期：2006.2

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.