1,8-diacetyloxy-9(10H)-anthracenone | 38165-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-diacetyloxy-9(10H)-anthracenone
• 英文别名: Acetic acid 8-acetoxy-9-oxo-9,10-dihydro-anthracen-1-yl ester；(8-acetyloxy-9-oxo-10H-anthracen-1-yl) acetate
• CAS: 38165-75-2
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: KZVNPJJZMRGJSL-UHFFFAOYSA-N

物化性质

• 沸点：
  508.8±50.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,8-diacetyloxy-9(10H)-anthracenone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 10-溴-1,8-二羟基-10H-蒽-9-酮
  参考文献：
  名称：

  AWE; KUEMMELL, Archiv der Pharmazie, 1960, vol. 293 /65, p. 271 - 277

  摘要：

  DOI：
• 作为产物：
  描述：

  地蒽酚 、 乙酸酐 生成 1,8-diacetyloxy-9(10H)-anthracenone
  参考文献：
  名称：

  Wiegrebe; Gerber; Kappler, Arzneimittel-Forschung/Drug Research, 1979, vol. 29, # 8, p. 1083 - 1088

  摘要：

  DOI：

文献信息

• Syntheses of Anthracenones. 3. Revised Preparative Route to 10-Benzoyl-1,8-dihydroxy-9(10<i>H</i>)-anthracenones
  作者：Helge Prinz、Wolfgang Wiegrebe、Klaus Müller

  DOI：10.1021/jo952037l

  日期：1996.1.1

  8-diacetoxy-9(10H)-anthracenone with benzoyl chloride and sodium hydride in THF followed by hydrolysis of an intermediate enol ester. Furthermore, when benzoyl chloride and DMF were used for the acylation of anthralin, a Vilsmeier-type reaction was observed leading to a novel enamine derivative of anthralin which was hydrolyzed or benzoylated to an enol or enol ester, respectively.

  发现蒽林（1,8-二羟基-9（10H）-蒽酮）与乙酰水杨酰氯在甲苯和可力丁中的酰化作用产生的是O-酰化产物，而不是10-（乙酰水杨基）蒽林。描述了在10位上的蒽醌苯甲酰化的方法，该方法包括使1，8-二乙酰氧基-9（10H）-蒽酮与苯甲酰氯和氢化钠在THF中反应，然后水解中间体烯醇酯。此外，当苯甲酰氯和DMF用于蒽环的酰化时，观察到Vilsmeier型反应，导致蒽环的新烯胺衍生物水解或苯甲酰化为烯醇酯或烯醇酯。
• Potent Antipsoriatic Agents: A Facile Preparation of Acylated Derivatives from Dithranol in a Mild Basic Reaction
  作者：David Woei-Ming Liang、Chun-Jian Du

  DOI：10.1002/jccs.200400018

  日期：2004.2

  Treatment of dithranol 1 with various equivalents of acetyl chloride and Et 3 N in THF at room temperature afforded the corresponding acylated derivatives, such as 1-acetyloxy- and 1,8-diacetyloxy-9(10H)-anthracenones, 6a,and 6b, as well as 1,8,9-triacetyloxyanthracene 7a, and 1,8,9-triacetyloxy-10-acetylanthracene 7b. 1,8-Bis(trimethylacetyloxy)-9(10H)-anthracenone 6c was also obtained in high yield

  在室温下，用各种当量的乙酰氯和 Et 3 N 在 THF 中处理联蒽酚 1，得到相应的酰化衍生物，例如 1-乙酰氧基-和 1,8-二乙酰氧基-9(10H)-蒽酮、6a 和 6b，以及1,8,9-三乙酰氧基蒽7a和1,8,9-三乙酰氧基-10-乙酰基蒽7b。1,8-双(三甲基乙酰氧基)-9(10H)-蒽酮6c也通过在温和酰化过程中使用新戊酰氯以高产率获得。
• 10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties
  作者：Klaus Müller、Reinhold Altmann、Helge Prinz

  DOI：10.1016/s0223-5234(98)80010-x

  日期：1998.3

  The synthesis and biological properties of 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones are described. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5-lipoxygenase enzyme in bovine polymorphonuclear leukocytes. In addition. generation of hydroxyl radicals was determined as measured by deoxyribose degradation. The results obtained with the new compounds show that substitution with a 4-hydroxy (4f) or a 4-benzyloxy group (4i) at the phenyl ring of the C-10 substituent resulted in potent antiproliferative agents. No correlation was found between hydroxyl-radical formation and the 5-LO inhibitory or antiproliferative action of the compounds. (C) Elsevier, Paris.
• Lambelet, Pierre; Prior, Elizabeth; Loeliger, Juerg, Journal of the Chemical Society. Perkin transactions II, 1990, # 9, p. 1509 - 1513
  作者：Lambelet, Pierre、Prior, Elizabeth、Loeliger, Juerg、Shroot, Braham

  DOI：——

  日期：——
• [EN] COMPOSITION COMPRISING AT LEAST ONE ANTHRONE DERIVATIVE AND ONE BASIFYING AGENT, AND METHOD FOR DYEING KERATINOUS FIBRES STARTING FROM THE COMPOSITION<br/>[FR] COMPOSITION COMPRENANT AU MOINS UN DÉRIVÉ D'ANTHRONE ET UN AGENT DE BASIFICATION, ET PROCÉDÉ DESTINÉ À COLORER DES FIBRES KÉRATINIQUES À PARTIR DE CETTE COMPOSITION
  申请人：OREAL

  公开号：WO2011045404A2

  公开（公告）日：2011-04-21

  A subject-matter of the invention is a composition for the dyeing of keratinous fibres comprising at least one anthrone derivative and at least one basifying agent, the use of the composition in hair dyeing and the use of the composition in a dyeing method. The dyeing method according to the invention makes it possible to dye keratinous fibres with anthrone derivatives under mild oxidizing conditions, even without using an oxidation base and an aromatic amine, while covering a broad palette of colours. The dyeing under oxidizing conditions observed operates under mild conditions of oxidation and/or of alkaline agent, in particular exposed to the air.