5,8-dihydroxy-2,7-dimethoxy-3-chloro-6-ethyl-1,4-naphthoquinone | 475084-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dihydroxy-2,7-dimethoxy-3-chloro-6-ethyl-1,4-naphthoquinone
• 英文别名: 6-chloro-3-ethyl-5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone；5,8-dihydroxy-3,6-dimethoxy-2-chloro-7-ethyl-1,4-naphthoquinone
• CAS: 475084-16-3
• 化学式: C₁₄H₁₃ClO₆
• 分子量: 312.707
• InChiKey: NSHYSFIEIHKGSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 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：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

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

  甲醇 、 6,7-dichloro-3-ethyl-5,8-dihydroxy-2-methoxy-1,4-naphthoquinone 在 aluminum oxide 、 cesium fluoride 作用下， 反应 1.0h， 以50%的产率得到5,8-dihydroxy-2,6-dimethoxy-3-chloro-7-ethyl-1,4-naphthoquinone
  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

文献信息

• ——
  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.