5,8-diacetoxy-benzo[rst]pentaphene | 3509-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 5,8-diacetoxy-benzo[rst]pentaphene
• 英文别名: 5,8-Diacetoxy-benzo[rst]pentaphen；5,8-Diacetoxy-3,4,9,10-dibenzpyren；Benzo[rst]pentaphene-5,8-diyl diacetate；(13-acetyloxy-8-hexacyclo[10.10.2.02,7.09,23.014,19.020,24]tetracosa-1(23),2,4,6,8,10,12,14,16,18,20(24),21-dodecaenyl) acetate
• CAS: 3509-60-2
• 化学式: C₂₈H₁₈O₄
• 分子量: 418.449
• InChiKey: WMQAIOGPASQFBI-UHFFFAOYSA-N

物化性质

• 熔点：
  332 °C(Solv: xylene (1330-20-7))
• 沸点：
  658.6±28.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯并[a,i]芘 在 chromium(VI) oxide 、 乙酸酐 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 5,8-diacetoxy-benzo[rst]pentaphene
  参考文献：
  名称：

  Investigation of the Metabolism of 3,4,9,10-Dibenzpyrene

  摘要：

  DOI：

  10.1021/jo01051a063

文献信息

• Anthraquinone and anthrone series—XXII
  作者：B.D. Tilak、M.K. Unni、K. Venkataraman

  DOI：10.1016/s0040-4020(01)82611-9

  日期：1958.1

  Indanthrene scarlet 4G with Raney nickel, aqueous sodium hydroxide and hydrogen. Reduction of (II) with aluminium tricyclohexoxide gave 3:4:9:10-dibenzopyrene (I), a potent carcinogen, which was isolated by Bonnet and Neukomm from tobacco smoke. Oxidation of 3:4:9:10-dibenzopyrene-5:8-quinone with chromic acid in glacial acetic acid gave pentaphene-5:14:8:13-diquinone (V). Reduction of (V) with aluminium

  Mayvat艳红AF被鉴定为3：4：9：10-二苯并py 5：8-醌（II）的卤代衍生物，后者是通过Mayvat艳红AF或Indanthrene猩红色4G与阮内镍脱卤而获得的，氢氧化钠水溶液和氢气。与铝，三（II）的还原环4：己醇，得到3 9：10-二苯并芘（I），一种有效的致癌物质，将其从烟草烟雾中分离由阀盖和Neukomm。在冰醋酸中用铬酸氧化3：4：9：10-二苯并re-5：8-醌，得到五苯乙酮-5：14：8：13-二醌（V）。有铝（V）的还原三环己醇，得到戊芬（VI）。的（V）缩合用肼，得到1:2二氮杂- 3：4：9：10-二苯并芘-5：8-醌（VII），减少其与铝的三环己氧化物产生1：2-二氮杂-3：4：9：10-二苯并py（VIII）。
• One-electron oxidation of dibenzo[a]pyrenes by manganic acetate
  作者：Paolo Cremonesi、Bruce Hietbrink、Eleanor G. Rogan、Ercole L. Cavalieri

  DOI：10.1021/jo00038a015

  日期：1992.6

  The dibenzo[a]pyrenes (DB[a]Ps) are carcinogenic polycyclic aromatic hydrocarbons (PAH) found as environmental pollutants. DB[a,l]P is the most potent carcinogenic PAH ever tested. To investigate the bioactivation of DB[a]Ps by one-electron oxidation, oxidation of DB[a,e]P, DB[a,h]P, DB[a,i]P, DB[a,l]P, and anthanthrene with Mn(OAc)3 was conducted and compared to that of benzo[a]pyrene (B[a]P). All five DB[a]Ps produced monoacetoxy derivatives, and all of them except DB[a,l]P also produced diacetoxy derivatives. Kinetic studies of the formation of monoacetoxy and diacetoxy derivatives of DB[a]Ps were carried out, and the results were compared to those of the parent compound B[a]P. DB[a,l]P was similar to B[a]P. DB[a,e]P reacted inefficiently to form monoacetoxy and diacetoxy products. The other three DB[a]Ps resembled one another. These results provide preliminary essential information for studies of the bioactivation of the very potent carcinogen DB[a,l]P to form DNA adducts.
• Investigation of the Metabolism of 3,4,9,10-Dibenzpyrene
  作者：ENVARE ÜNSEREN、LOUIS F. FIESER

  DOI：10.1021/jo01051a063

  日期：1962.4