1-(allyloxy)-8-methoxy-9,10-anthraquinone | 85313-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(allyloxy)-8-methoxy-9,10-anthraquinone
• 英文别名: 1-allyloxy-8-methoxyanthracene-9,10-dione；9,10-Anthracenedione, 1-methoxy-8-(2-propenyloxy)-；1-methoxy-8-prop-2-enoxyanthracene-9,10-dione
• CAS: 85313-87-7
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: LXLNDKWBLWRFDO-UHFFFAOYSA-N

物化性质

• 沸点：
  478.3±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-(allyloxy)-8-methoxy-9,10-anthraquinone 在 sodium hydroxide 、 sodium dithionite 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 2-(2',3'-epoxypropyl)-1-hydroxy-8-methoxy-9,10-anthraquinone
  参考文献：
  名称：

  Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G

  摘要：

  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.

  DOI：

  10.1021/jm00087a014
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 氢氧化钾 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 124.0h， 生成 1-(allyloxy)-8-methoxy-9,10-anthraquinone
  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

• Syntheses of Anthracenones. 1. Sodium Dithionite Reduction of <i>peri</i>-Substituted Anthracenediones
  作者：Helge Prinz、Wolfgang Wiegrebe、Klaus Müller

  DOI：10.1021/jo9520351

  日期：1996.1.1

  The reaction of peri-substituted anthracenediones with sodium dithionite in dimethylformamide and water has been investigated. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 4,5-disubstituted 9(10H)-anthracenones and thus provides a route to anthracenones which are otherwise difficult to obtain. Many functional groups

  研究了过取代的蒽二酮与连二亚硫酸钠在二甲基甲酰胺和水中的反应。该体系选择性地还原蒽二酮的周围取代基侧接的羰基，得到相应的4，5-二取代的9（10H）-蒽酮，因此提供了一种难以获得的蒽酮途径。可以容许许多官能团，该反应与起始的蒽二酮的周边烷氧基和不饱和侧链的存在相容，并且还原不超过蒽酮阶段。然而，蒽酮的形成取决于周围取代基的性质。从1，8-二甲基取代的蒽二酮和没有取代基的母体化合物没有得到产物。
• Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids
  作者：Nadali, Samaneh、Khoshroo, Ali、Aghapour, Ghasem

  DOI：10.3906/kim-1711-49

  日期：——

  A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones to 1-hydroxy-2-(prop-2'-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF$_4}$ (1-methylimidazolium tetrafluoroborate), in short reaction times (5-35 min). Our study showed that 1-(prop-2'-enyloxy)anthraquinone is more active than 1-(2'-chloroprop-2'-enyloxy)anthraquinone to perform this rearrangement.

  本研究介绍了铁介导的各种丙-2'-烯氧基蒽醌和 2'-氯丙-2'-烯氧基蒽醌到 1-羟基-2-(丙-2'-烯基)蒽醌和蒽呋喃酮的快速和选择性还原性克莱森重排反应。 所有反应均在离子液体[Bzmim]Cl（1-苄基-3-甲基咪唑氯化物）和[Hmim]BF$_4}$（1-甲基咪唑四氟硼酸盐）的混合物中进行，反应时间短（5-35 分钟）。我们的研究表明，1-(丙-2'-烯氧基)蒽醌比 1-(2'-氯丙-2'-烯氧基)蒽醌在进行这种重排反应时更为活跃。
• Claisen Rearrangement of Allyloxyanthraquinones with Silver/Potassium Iodide in Acetic Acid as a New and Efficient Reagent
  作者：Hashem Sharghi、Ghasem Aghapour

  DOI：10.1021/jo991674z

  日期：2000.5.1
• Glucose Promoted Claisen Rearrangement of 1-Allyloxy Anthraquinones
  作者：Kadiyala V. S. N. Murty、Ranjan Pal、Kalyani Datta、Dipakranjan Mal

  DOI：10.1080/00397919408011730

  日期：1994.5

  Glucose effects the Claisen rearrangement of allyloxy anthraquinones at low temperatures(100-130-degrees-C).
• 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.