1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone | 145146-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone
• 英文别名: 1,4-dihydro-5-hydroxy-1,4-ethano-9,10-anthraquinone；5-Hydroxy-1,4-dihydro-1,4-ethanoanthracene-9,10-dione；5-hydroxytetracyclo[10.2.2.02,11.04,9]hexadeca-2(11),4(9),5,7,13-pentaene-3,10-dione
• CAS: 145146-97-0
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: PNEYUXMYBRUGJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone 、 碘甲烷 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到(+/-)-1,4-Ethano-5-methoxy-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036
• 作为产物：
  描述：

  5-羟基对萘醌 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 312.0h， 生成 1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  醌的研究。第40部分：蒽醌环氧化物和异构化产物的合成和细胞毒性评估

  摘要：

  在二氯甲烷-DBU中对1,4,4a，10a-四氢-1,4-链烷-5,10-蒽醌和噻吩类似物进行有氧氧化，生成相应的二氢链烷醌，根据其结构，它们与原位生成的氢过氧化物阴离子反应得到环氧化物醌和/或氢过氧化物。氢氧化钙诱导的醌环氧化物的重排产生了含呋喃的角醌。在体外评估了醌环氧化物及其异构化产物对正常人肺成纤维细胞（MRC-5）和人癌胃上皮细胞（AGS）的细胞毒活性。

  DOI：

  10.1016/j.tet.2005.12.038

文献信息

• A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)
  作者：Allimuthu T. Dharmaraja、Harinath Chakrapani

  DOI：10.1021/ol403300a

  日期：2014.1.17

  Due to the short half-life of reactive oxygen species (ROS) such as a superoxide radical, controlled and localized generation of ROS is challenging. Here, we report a rationally designed small-molecule 1c that generates ROS only when triggered by a bacterial enzyme. We provide evidence for 1c predictably enhancing the intracellular superoxide radical in a model bacterium. Spatiotemporal control over ROS generation offered by 1c should help better understand stress responses in bacteria to increased ROS.
• Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones
  作者：M. Carmen Carreno、Jose L. Garcia Ruano、Antonio Urbano

  DOI：10.1021/jo00051a036

  日期：1992.12

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.
• Studies on quinones. Part 40: Synthesis and cytotoxicity evaluation of anthraquinone epoxides and isomerization products
  作者：Jaime A. Valderrama、Omar Espinoza、M. Florencia González、Ricardo A. Tapia、Jaime A. Rodríguez、Cristina Theoduloz、Guillermo Schmeda-Hirschmann

  DOI：10.1016/j.tet.2005.12.038

  日期：2006.3

  dihydroalkanoquinones which, depending on their structures, react with in situ generated hydroperoxide anion to give quinone epoxides and/or hydroperoxides. The calcium hydroxide-induced rearrangement of quinone epoxides yielded furan-containing angular quinones. The cytotoxic activities of quinone epoxides and their isomerization products were evaluated in vitro against normal human lung fibroblasts (MRC-5) and

  在二氯甲烷-DBU中对1,4,4a，10a-四氢-1,4-链烷-5,10-蒽醌和噻吩类似物进行有氧氧化，生成相应的二氢链烷醌，根据其结构，它们与原位生成的氢过氧化物阴离子反应得到环氧化物醌和/或氢过氧化物。氢氧化钙诱导的醌环氧化物的重排产生了含呋喃的角醌。在体外评估了醌环氧化物及其异构化产物对正常人肺成纤维细胞（MRC-5）和人癌胃上皮细胞（AGS）的细胞毒活性。