endo-1,4-Ethano-5-hydroxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone | 131924-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: endo-1,4-Ethano-5-hydroxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone
• 英文别名: JCHD；5-Hydroxy-1,4,4a,9a-tetrahydro-1,4-ethanoanthracene-9,10-dione；5-hydroxytetracyclo[10.2.2.02,11.04,9]hexadeca-4(9),5,7,13-tetraene-3,10-dione
• CAS: 131924-05-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: PGASHFHOCSXRLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  endo-1,4-Ethano-5-hydroxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone 在 E_. coli nitroreductase 、 还原型辅酶II(NADPH)四钠盐 、 silver(l) oxide 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)

  摘要：

  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.

  DOI：

  10.1021/ol403300a
• 作为产物：
  描述：

  5-羟基对萘醌 、 1,3-环己二烯 反应 12.0h， 生成 endo-1,4-Ethano-5-hydroxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone
  参考文献：
  名称：

  Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors

  摘要：

  在此，我们报告了5-羟基-1,2,3,4,4a,9a-六氢-1,4-乙烯-9,10-蒽醌（13），这是一种在pH 7.4缓冲液中、在常温好氧条件下生成活性氧（ROS）的小分子，具有选择性和强效的抗结核分枝杆菌生长抑制活性。

  DOI：

  10.1039/c2cc35343a

文献信息

• Photocontrolled endogenous reactive oxygen species (ROS) generation
  作者：Ajay Kumar Sharma、Harshit Singh、Harinath Chakrapani

  DOI：10.1039/c9cc01747j

  日期：——

  A cell-permeable small molecule for light-triggered generation of endogenous reactive oxygen species (ROS) is reported.

  报道了一种细胞可渗透的小分子，用于光触发内源性活性氧（ROS）的产生。
• 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.