8,9-dehydro-ζ-rhodomycinone 8,9-α-epoxide | 75324-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 8,9-dehydro-ζ-rhodomycinone 8,9-α-epoxide
• 英文别名: Naphthaceno(2,3-b)oxirene-2-carboxylic acid, 1a-ethyl-1a,2,4,9,11,11a-hexahydro-3,8,10-trihydroxy-4,9-dioxo-, methyl ester, (1aS-(1aalpha,2alpha,11aalpha))-；methyl (4R,5S,7R)-5-ethyl-2,10,14-trihydroxy-12,19-dioxo-6-oxapentacyclo[9.8.0.03,9.05,7.013,18]nonadeca-1,3(9),10,13(18),14,16-hexaene-4-carboxylate
• CAS: 75324-03-7
• 化学式: C₂₂H₁₈O₈
• 分子量: 410.38
• InChiKey: SLOAUJRRFDJQDU-ZQNCNBDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8,9-dehydro-ζ-rhodomycinone 8,9-α-epoxide 在 高氯酸 作用下， 以 丙酮 为溶剂， 反应 144.0h， 以54%的产率得到8β-hydroxy-ζ-rhodomycinone
  参考文献：
  名称：

  8-Hydroxyanthracyclinones from .epsilon.-rhodomycinone

  摘要：

  epsilon-Rhodomycinone was converted into 8,9-dehydro-zeta-rhodomycinone, which gave a cis diol with osmium tetroxide and a pair of epimeric epoxides with m-chloroperbenzoic acid. Acid-catalyzed opening of the epoxides gave the corresponding trans diols. In contrast, acid treatment of the trimethyl ethers of these epoxides gave predominantly a lactone and an eta-rhodomycinone derivative, with only small amounts of the diols. None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-zeta-rhodomycinone was active in the induction of lytic phage in Escherichia coli.

  DOI：

  10.1021/jm00185a020
• 作为产物：
  描述：

  ζ-rhodomycinone 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 8,9-dehydro-ζ-rhodomycinone 8,9-α-epoxide
  参考文献：
  名称：

  8-Hydroxyanthracyclinones from .epsilon.-rhodomycinone

  摘要：

  epsilon-Rhodomycinone was converted into 8,9-dehydro-zeta-rhodomycinone, which gave a cis diol with osmium tetroxide and a pair of epimeric epoxides with m-chloroperbenzoic acid. Acid-catalyzed opening of the epoxides gave the corresponding trans diols. In contrast, acid treatment of the trimethyl ethers of these epoxides gave predominantly a lactone and an eta-rhodomycinone derivative, with only small amounts of the diols. None of the new rhodomycinones were active against Bacillus subtilis, but 8,9-dehydro-zeta-rhodomycinone was active in the induction of lytic phage in Escherichia coli.

  DOI：

  10.1021/jm00185a020