5-hydroxy-4,9-dimethoxy-2-methyl-11-phenyl-benzo[b]fluoren-10-one | 870465-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-hydroxy-4,9-dimethoxy-2-methyl-11-phenyl-benzo[b]fluoren-10-one
• 英文别名: 5-Hydroxy-4,9-dimethoxy-2-methyl-11-phenylbenzo[b]fluoren-10-one；5-hydroxy-4,9-dimethoxy-2-methyl-11-phenylbenzo[b]fluoren-10-one
• CAS: 870465-38-6
• 化学式: C₂₆H₂₀O₄
• 分子量: 396.442
• InChiKey: SNOYIFGXFZILQM-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C (decomp)
• 沸点：
  644.1±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,9-dimethoxy-2-methyl-11-phenyl-benzo[b]fluoren-10-one 、 苄硫醇 反应 2.0h， 以94%的产率得到11-benzylsulfanyl-4,9-dimethoxy-2-methyl-11-phenyl-benzo[b]fluorene-5,10-diol
  参考文献：
  名称：

  Studies on the Mechanism of Action of Prekinamycin, a Member of the Diazoparaquinone Family of Natural Products:  Evidence for Both sp² Radical and Orthoquinonemethide Intermediates

  摘要：

  The putative reductive activation chemistry of the diazoparaquinone antibiotics was modeled with Bu3Sn-H and prekinamycin dimethyl ether along with prekinamycin itself. Reaction in various combinations of aromatic solvents, with and without the nucleophile benzylmercaptan present, led to isolation of both radical-trapping arene adducts and nucleophilic capture benzyl thioether products. On the basis of these product distribution studies, the intermediacies of, first, a cyclopentenyl radical and, next, an orthoquinonemethide electrophile are postulated.

  DOI：

  10.1021/ja0642616
• 作为产物：
  描述：

  5-diazo-1,7-dimethoxy-3-methyl-5H-benzo[b]fluoren-6,11-dione 、 苯 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以79%的产率得到5-hydroxy-4,9-dimethoxy-2-methyl-11-phenyl-benzo[b]fluoren-10-one
  参考文献：
  名称：

  Studies on the Mechanism of Action of Prekinamycin, a Member of the Diazoparaquinone Family of Natural Products:  Evidence for Both sp² Radical and Orthoquinonemethide Intermediates

  摘要：

  The putative reductive activation chemistry of the diazoparaquinone antibiotics was modeled with Bu3Sn-H and prekinamycin dimethyl ether along with prekinamycin itself. Reaction in various combinations of aromatic solvents, with and without the nucleophile benzylmercaptan present, led to isolation of both radical-trapping arene adducts and nucleophilic capture benzyl thioether products. On the basis of these product distribution studies, the intermediacies of, first, a cyclopentenyl radical and, next, an orthoquinonemethide electrophile are postulated.

  DOI：

  10.1021/ja0642616

文献信息

• A Proposal for the Mechanism-of-Action of Diazoparaquinone Natural Products
  作者：Ken S. Feldman、Kyle J. Eastman

  DOI：10.1021/ja053880w

  日期：2005.11.1

  Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.
• Studies on the Mechanism of Action of Prekinamycin, a Member of the Diazoparaquinone Family of Natural Products:  Evidence for Both sp² Radical and Orthoquinonemethide Intermediates
  作者：Ken S. Feldman、Kyle J. Eastman

  DOI：10.1021/ja0642616

  日期：2006.9.1

  The putative reductive activation chemistry of the diazoparaquinone antibiotics was modeled with Bu3Sn-H and prekinamycin dimethyl ether along with prekinamycin itself. Reaction in various combinations of aromatic solvents, with and without the nucleophile benzylmercaptan present, led to isolation of both radical-trapping arene adducts and nucleophilic capture benzyl thioether products. On the basis of these product distribution studies, the intermediacies of, first, a cyclopentenyl radical and, next, an orthoquinonemethide electrophile are postulated.