| 135513-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 四环素类
• CAS: 135513-28-9
• 化学式: C₂₁H₂₀N₂O₈
• 分子量: 428.398
• InChiKey: PNGZYTUSBGPAPU-UVPAEMEASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  184.12
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  米诺环素 在 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Identification and characterization of a tetracycline semiquinone formed during the oxidation of minocycline

  摘要：

  Oxidation of minocycline under slightly alkaline conditions produces a semiquinone free radical with hyperfine splittings that are atypical for a p-semiquinone. At high pH or on complexation with calcium and strontium, somewhat different spectra are observed, which are associated, respectively, with removal of the proton of the C-12 hydroxy group or with metal binding to the C-11-C-12-beta-diketone system. The initial oxidation of minocycline is a two-electron process with no detectable free-radical intermediate. Hydrolysis of the dimethylamino group of this oxidation product yields a quinone. The reduced form of the quinone has been isolated and, by comparison of its NMR spectra to those of minocycline, has been identified as the quinol, 7-hydroxy-6-deoxy-6-demethyltetracycline. Complete analyses of the H-1 NMR spectra of both minocycline and 7-hydroxy-6-deoxy-6-demethyltetracycline are presented. Reverse dismutation of the quinone and its hydroquinone gives a p-semiquinone radical: the first reported tetracycline semiquinone. A hyperfine splitting of 7 G, which is atypical for a p-semiquinone, is attributed to an axial beta-hydrogen proton adjacent to a position with a beta-carbonyl group.

  DOI：

  10.1021/jo00019a031