6-undecyl-1,2,4-trihydroxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-undecyl-1,2,4-trihydroxybenzene
• 英文别名: 6-Undecylbenzene-1,2,4-triol
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: BOKJRYKIAJNHJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  癸基溴 在 palladium on activated charcoal 氢气 、 碘 、 三溴化硼 、 对甲苯磺酸 、 magnesium 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 6-undecyl-1,2,4-trihydroxybenzene
  参考文献：
  名称：

  DNA cleavage by di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu(II), and alkali

  摘要：

  Several 5-alkyl-1,3-dihydroxybenzene (5-alkylresorcinol, 1) and 6-alkyl-1,2,4-trihydroxybenzene (2) derivatives were prepared and used to study the mechanism by which such compounds effect Cu(II)-dependent DNA strand scission. Comparison of the methyl, n-pentyl, n-undecyl, and n-hexadecyl derivatives in each structural series indicated that the efficiency of DNA cleavage increased with increasing length of the alkyl substituent. DNA cleavage by the 5-alkylresorcinols appears to involve initial oxygenation of the benzene nucleus, a process that occurs readily at alkaline pH in the presence of Cu2+ and O-2. The resulting trihydroxylated benzenes mediate DNA cleavage in a reaction dependent on the presence of both Cu2+ and O-2. The mechanism appears to involve reduction of CU2+ by the trihydroxybenzene moiety in 2, with subsequent formation of reactive oxygen species. The ability of catalase and dimethyl sulfoxide to suppress DNA strand scission is consistent with the intermediacy of H2O2 and (OH)-O-. in the DNA strand scission process.

  DOI：

  10.1021/ja00156a005

文献信息

• DNA cleavage by di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu(II), and alkali
  作者：Udai S. Singh、Ralph T. Scannell、Haoyun An、Barbara J. Carter、Sidney M. Hecht

  DOI：10.1021/ja00156a005

  日期：1995.12

  Several 5-alkyl-1,3-dihydroxybenzene (5-alkylresorcinol, 1) and 6-alkyl-1,2,4-trihydroxybenzene (2) derivatives were prepared and used to study the mechanism by which such compounds effect Cu(II)-dependent DNA strand scission. Comparison of the methyl, n-pentyl, n-undecyl, and n-hexadecyl derivatives in each structural series indicated that the efficiency of DNA cleavage increased with increasing length of the alkyl substituent. DNA cleavage by the 5-alkylresorcinols appears to involve initial oxygenation of the benzene nucleus, a process that occurs readily at alkaline pH in the presence of Cu2+ and O-2. The resulting trihydroxylated benzenes mediate DNA cleavage in a reaction dependent on the presence of both Cu2+ and O-2. The mechanism appears to involve reduction of CU2+ by the trihydroxybenzene moiety in 2, with subsequent formation of reactive oxygen species. The ability of catalase and dimethyl sulfoxide to suppress DNA strand scission is consistent with the intermediacy of H2O2 and (OH)-O-. in the DNA strand scission process.