2-allyl-1,8-dimethoxyanthracene-9,10-dione | 85313-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-allyl-1,8-dimethoxyanthracene-9,10-dione
• 英文别名: 1,8-Dimethoxy-2-prop-2-enylanthracene-9,10-dione
• CAS: 85313-89-9
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: CUOACMDJIPKRBT-UHFFFAOYSA-N

物化性质

• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2-allyl-1,8-dimethoxyanthracene-9,10-dione 在 B2H6-THF 作用下， 反应 23.0h， 以71%的产率得到3-(1,8-dimethoxy-9,10-dioxyanthracene-2-yl)propan-1-ol
  参考文献：
  名称：

  Studies on the synthesis of 4-(1,8-dioxygenated-9,10-dioxoanthracen(or anthracen)-2-yl)butanoic acid derivatives.

  摘要：

  所述化合物（11-14, 16, 17）预计在合成11-脱氧蒽醌酮中具有重要价值，采用易得的1,8-二羟基蒽-9,10-二酮（千层石（chrysazin））（3）作为原料，通过克莱森重排或马尔沙尔克反应作为关键合成步骤制备而成。

  DOI：

  10.1248/cpb.30.4539
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 氢氧化钾 、 2,6-二叔丁基苯酚 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 149.0h， 生成 2-allyl-1,8-dimethoxyanthracene-9,10-dione
  参考文献：
  名称：

  Studies on the synthesis of 4-(1,8-dioxygenated-9,10-dioxoanthracen(or anthracen)-2-yl)butanoic acid derivatives.

  摘要：

  所述化合物（11-14, 16, 17）预计在合成11-脱氧蒽醌酮中具有重要价值，采用易得的1,8-二羟基蒽-9,10-二酮（千层石（chrysazin））（3）作为原料，通过克莱森重排或马尔沙尔克反应作为关键合成步骤制备而成。

  DOI：

  10.1248/cpb.30.4539

文献信息

• Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G
  作者：David E. Zembower、Chih Min Kam、James C. Powers、Leon H. Zalkow

  DOI：10.1021/jm00087a014

  日期：1992.5

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.
• Studies on the synthesis of 4-(1,8-dioxygenated-9,10-dioxoanthracen(or anthracen)-2-yl)butanoic acid derivatives.
  作者：ICHIRO TAKAHASHI、SHIRO TERASHIMA

  DOI：10.1248/cpb.30.4539

  日期：——

  The title compounds (11-14, 16, 17), which are expected to be valuable in the synthesis of 11-deoxyanthracyclinones, were prepared from readily available 1, 8-dihydroxyan-thracene-9, 10-dione (chrysazin) (3) by employing the Claisen rearrangement or Marschalk reaction as a key synthetic step.

  所述化合物（11-14, 16, 17）预计在合成11-脱氧蒽醌酮中具有重要价值，采用易得的1,8-二羟基蒽-9,10-二酮（千层石（chrysazin））（3）作为原料，通过克莱森重排或马尔沙尔克反应作为关键合成步骤制备而成。