3-chloro-2,5,7,8-tetrahydroxy-1,4-naphthoquinone | 367922-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-2,5,7,8-tetrahydroxy-1,4-naphthoquinone
• CAS: 367922-82-5
• 化学式: C₁₀H₅ClO₆
• 分子量: 256.599
• InChiKey: WHLZXPAZZYISIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115.06
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-chloro-2,5,7,8-tetrahydroxy-1,4-naphthoquinone 以 乙醚 为溶剂， 以62%的产率得到6-chloro-2,5,8-trihydroxy-7-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  摘要：

  A set of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins were synthesized. The IR spectra of 2-hydroxy-6-methoxynaphthazarins and 7-hydroxypyranonaphthazarins, on the one hand, and of 2-hydroxy-7-methoxynaphthazarins and 8-hydroxypyranonaphthazarins, on the other hand, have the characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. These regularities confirm the structures of cristazarin and 6-methylcristazarin, which are metabolites of lichen Cladonia cristatella.

  DOI：

  10.1023/a:1009533403588
• 作为产物：
  描述：

  5,8-dihydroxy-2-methoxy-6,7-dichloro-1,4-naphthoquinone 在 potassium fluoride 、 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 20.5h， 生成 3-chloro-2,5,7,8-tetrahydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  First direct observation of tautomerism of monohydroxynaphthazarins by IR-spectroscopy

  摘要：

  Some substituted monohydroxylated naphthazarins (5,8-dihydroxy-1,4-naphthoquinones) were synthesized and studied by IR-spectroscopy in aprotic organic solvents at ambient temperature. Two narrow stretching mode bands in the high frequency range 3540-3410 cm(-1) due to a beta-hydroxy group were observed; it was established that this effect was caused by tautomerism. This allowed the creation of a convenient and accurate method for the measurement of a small amount of tautomer engaged in rapid exchange with the principal tautomer. Solvent and substituent effects were estimated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00060-1