2-acetyl-3-chloro-1,4-benzoquinone | 52095-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-3-chloro-1,4-benzoquinone
• 英文别名: 2-acetil-3-cloro-1,4-benzoquinona；2-acetyl-3-chlorocyclohexa-2,5-diene-1,4-dione
• CAS: 52095-13-3
• 化学式: C₈H₅ClO₃
• 分子量: 184.579
• InChiKey: ZLURBXQNDDALMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-chloro-1,4-benzoquinone 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-(5-Chloro-3,6-dihydroxy-4-tricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraenyl)ethanone
  参考文献：
  名称：

  Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones

  摘要：

  Acylhydroquinone-based compounds are attractive targets for the design of new leishmanicidal drugs. We have previously described sesquiterpene quinones and hydroquinones series, which exhibit different degree of potency against Leishmania amazonensis. The present study details the preparation of acylchloroquinones and hydroquinones possessing lipophilic substituents and examines their in vitro activity against intracellular L. amazonensis amastigotes. The quinone or hydroquinone nucleus is essential for the activity of the members of the series. The lipophilicity of the cycloaliphatic systems in these members seems to attenuate the cytotoxical effect and increases the selectivity of those compounds containing the norbornene system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.041
• 作为产物：
  描述：

  1-(2-chloro-3,6-dihydroxyphenyl)ethanone 在 manganese(IV) oxide 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到2-acetyl-3-chloro-1,4-benzoquinone
  参考文献：
  名称：

  Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones

  摘要：

  Acylhydroquinone-based compounds are attractive targets for the design of new leishmanicidal drugs. We have previously described sesquiterpene quinones and hydroquinones series, which exhibit different degree of potency against Leishmania amazonensis. The present study details the preparation of acylchloroquinones and hydroquinones possessing lipophilic substituents and examines their in vitro activity against intracellular L. amazonensis amastigotes. The quinone or hydroquinone nucleus is essential for the activity of the members of the series. The lipophilicity of the cycloaliphatic systems in these members seems to attenuate the cytotoxical effect and increases the selectivity of those compounds containing the norbornene system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.041

文献信息

• Farina, F.; Valderrama, J. A., Anales de Quimica, 1995, vol. 91, # 3-4, p. 230 - 235
  作者：Farina, F.、Valderrama, J. A.

  DOI：——

  日期：——
• Farina, F.; Valderrama, J. A.; Gonzalez, Y. L., Anales de Quimica, 1995, vol. 91, # 5-6, p. 440 - 448
  作者：Farina, F.、Valderrama, J. A.、Gonzalez, Y. L.

  DOI：——

  日期：——