3-amino-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-1,4-naphthoquinone | 866229-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-1,4-naphthoquinone
• CAS: 866229-66-5
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: KICSQPUQWCYHTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  119.08
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-amino-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-1,4-naphthoquinone 在 氢溴酸 、 溶剂黄146 作用下， 以91%的产率得到3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-dihydronaphthlene-1,4-dione
  参考文献：
  名称：

  Synthesis of Echinamines A and B, the First Aminated Hydroxynaphthazarins Produced by the Sea Urchin Scaphechinus mirabilis and Its Analogues

  摘要：

  The first total synthesis of two marine aminated hydroxynaphthazarins, echinamines A (3-amino-7-ethyl- 2,5,6,8-tetrahydroxy-1,4- naphthoquinone) and B (2-amino-7-ethyl- 3,5,6,8-tetrahydroxy-1,4- naphthoquinone), produced by the sea urchin Scaphechinus mirabilis is described. This was achieved from 1,2,4-triacetoxybenzene (13) through a sequence involving double Fries rearrangement of 13, reduction of 3,5-diacetyl-1,2,4-trihydroxybenzene (14), methylation of 3,5-diethyl-1,2,4- trihydroxybenzene (15), simultaneous double acylation of 3,5-diethyl-1,2,4- trimethoxybenzene ( 16) with a dichloromaleic anhydride-ethyl radical elimination process, methylation of 6,7-dichloro-3-ethyl-2-hydroxynaphthazarin (17), nucleophilic substitution of a chlorine atom by the methoxy group in 6,7-dichloro-3-ethyl-2-methoxynaphthazarin (18), introduction of an amino group via direct substitution of a chlorine atom in 7-chloro-3-ethyl-2,6- dimethoxy- (11) and 7-chloro-2-ethyl-3,6-dimethoxynaphthazarins (12) by an azido group, and functional group deprotection. The synthesis of amino analogues of spinazarin and spinochrome D is also described.

  DOI：

  10.1021/np0502185
• 作为产物：
  描述：

  2-azido-3-chloro-7-ethyl-5,6,8-trihydroxynaphthalene-1,4-dione 在 sodium azide 、 potassium carbonate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-amino-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-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

文献信息

• Echinamines A and B, First Aminated Hydroxynaphthazarins from the Sea Urchin <i>Scaphechinus </i><i>m</i><i>irabilis</i>
  作者：Natalia P. Mischenko、Sergey A. Fedoreyev、Nataly D. Pokhilo、Victor Ph. Anufriev、Vladimir A. Denisenko、Valery P. Glazunov

  DOI：10.1021/np049585r

  日期：2005.9.1

  Two new spinochromes, echinamines A (1) and B (2), were isolated from the sea urchin Scaphechinus mirabilis. Compounds 1 and 2 represent the first examples of natural polyhydroxynaphthazarins with a primary amine group. The structures of 1 and 2 were established by analysis of spectroscopic data and synthesis of their dimethyl ethers.