1,6-Dimethoxyphenanthrene-9,10-dione | 1424243-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,6-Dimethoxyphenanthrene-9,10-dione
• 英文别名: 1,6-dimethoxyphenanthrene-9,10-dione
• CAS: 1424243-55-9
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: SHQWUKBMODAKDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-Dimethoxyphenanthrene-9,10-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到1,6-dihydroxy-phenanthrene-9,10-dione
  参考文献：
  名称：

  Synthesis of novel inhibitors blocking Wnt signaling downstream of β-Catenin

  摘要：

  Large scale screening of libraries consisting of natural and small molecules led to the identification of many small molecule inhibitors repressing Wnt/β‐Catenin signaling. However, targeted synthesis of novel Wnt pathway inhibitors has been rarely described. We developed a modular and expedient way to create the aromatic ring system with an aliphatic ring in between. Our synthesis opens up the possibility, in principle, to substitute all positions at the ring system with any desired substituent. Here, we tested five different haloquinone analogs carrying methoxy‐ and hydroxy‐groups at different positions. Bona fide Wnt activity assays in cell culture and in Xenopus embryos revealed that two of these compounds act as potent inhibitors of aberrant activated Wnt/β‐Catenin signaling.

  DOI：

  10.1016/j.febslet.2013.01.034
• 作为产物：
  描述：

  草酰氯 、 3,3-二甲氧基联苯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以41%的产率得到1,6-Dimethoxyphenanthrene-9,10-dione
  参考文献：
  名称：

  Rediscovering the Double Friedel-Crafts Acylation: An Expedient Entry to Phenanthrene-9,10-diones

  摘要：

  The double Friedel-Crafts acylation of readily accessible biaryls with oxalyl chloride delivers the respective phenanthrene-9,10-diones, providing an alternative to the traditional methods, which require harsh oxidizing conditions and multistep sequences. This simple method allows the synthesis of various symmetrical and non-symmetrical targets, and is even effective for the synthesis of the parent ring system from (unactivated) biphenyl.

  DOI：

  10.1055/s-0032-1318481

文献信息

• Rediscovering the Double Friedel-Crafts Acylation: An Expedient Entry to Phenanthrene-9,10-diones
  作者：Kye-Simeon Masters、Stefan Bräse、Nicoletta Crosta、Sebastian Müller、Dietmar Gradl

  DOI：10.1055/s-0032-1318481

  日期：——

  The double Friedel-Crafts acylation of readily accessible biaryls with oxalyl chloride delivers the respective phenanthrene-9,10-diones, providing an alternative to the traditional methods, which require harsh oxidizing conditions and multistep sequences. This simple method allows the synthesis of various symmetrical and non-symmetrical targets, and is even effective for the synthesis of the parent ring system from (unactivated) biphenyl.
• Synthesis of novel inhibitors blocking Wnt signaling downstream of β-Catenin
  作者：Sonja Halbedl、Marie-Claire Kratzer、Karolin Rahm、Nicoletta Crosta、Kye-Simeon Masters、Jessica Zippert、Stefan Bräse、Dietmar Gradl

  DOI：10.1016/j.febslet.2013.01.034

  日期：2013.3.1

  Large scale screening of libraries consisting of natural and small molecules led to the identification of many small molecule inhibitors repressing Wnt/β‐Catenin signaling. However, targeted synthesis of novel Wnt pathway inhibitors has been rarely described. We developed a modular and expedient way to create the aromatic ring system with an aliphatic ring in between. Our synthesis opens up the possibility, in principle, to substitute all positions at the ring system with any desired substituent. Here, we tested five different haloquinone analogs carrying methoxy‐ and hydroxy‐groups at different positions. Bona fide Wnt activity assays in cell culture and in Xenopus embryos revealed that two of these compounds act as potent inhibitors of aberrant activated Wnt/β‐Catenin signaling.