5,8-dihydroxy-2,6-dimethoxy-3-chloro-7-ethyl-1,4-naphthoquinone | 475084-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2,6-dimethoxy-3-chloro-7-ethyl-1,4-naphthoquinone
• 英文别名: 3-chloro-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-1,4-naphthoquinone；5,8-dihydroxy-3,7-dimethoxy-2-chloro-6-ethyl-1,4-naphthoquinone；Agn-PC-00ayx4；2-chloro-6-ethyl-5,8-dihydroxy-3,7-dimethoxynaphthalene-1,4-dione
• CAS: 475084-15-2
• 化学式: C₁₄H₁₃ClO₆
• 分子量: 312.707
• InChiKey: DKEWQHBQSSHPMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,8-dihydroxy-2,6-dimethoxy-3-chloro-7-ethyl-1,4-naphthoquinone 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 2-Azido-6-ethyl-5,8-dihydroxy-3,7-dimethoxynaphthalene-1,4-dione
  参考文献：
  名称：

  Echinamines A and B, First Aminated Hydroxynaphthazarins from the Sea Urchin Scaphechinus mirabilis

  摘要：

  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.

  DOI：

  10.1021/np049585r
• 作为产物：
  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

文献信息

• Synthesis of Echinamines A and B, the First Aminated Hydroxynaphthazarins Produced by the Sea Urchin <i>Scaphechinus </i><i>m</i><i>irabilis</i> and Its Analogues
  作者：Nataly D. Pokhilo、Maria I. Shuvalova、Maxim V. Lebedko、Galina I. Sopelnyak、Alla Ya. Yakubovskaya、Natalia P. Mischenko、Sergey A. Fedoreyev、Victor Ph. Anufriev

  DOI：10.1021/np0502185

  日期：2006.8.1

  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.
• 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.
• ——
  作者：T. Yu. Kochergina、V. F. Anufriev

  DOI：10.1023/a:1016551223482

  日期：——

  The nucleophilic substitution of halogen by methoxy groups in 5,8-dihydroxy-2,3-dichloro-1,4-naphthoquinones effected by complex reagent KF-MeOH-Al2O3 is considerably accelerated in the presence of electron-donor solvents.
• 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.