1-苯氧基蒽醌 | 17613-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-苯氧基蒽醌
• 英文名称: 1-phenoxy-anthraquinone
• 英文别名: 1-Phenoxy-anthrachinon；phenoxyanthraquinone；1-Phenoxyanthracene-9,10-dione
• CAS: 17613-65-9
• 化学式: C₂₀H₁₂O₃
• 分子量: 300.313
• InChiKey: HCXMMSVIJXNUQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  477.9±34.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苯氧基蒽醌 以 solid matrix 为溶剂， 生成 9-phenoxy-1,10-anthraquinone
  参考文献：
  名称：

  Eroshkin, V. I.; Fokin, E. P.; Volkov, A. I., Russian Journal of Physical Chemistry, 1991, vol. 65, # 6, p. 784 - 787

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯蒽醌 、 苯酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到1-苯氧基蒽醌
  参考文献：
  名称：

  Alkynes and poly(ethylene glycol) derivatives as nucleophiles and catalysts in substitution reactions of 1-chloroanthraquinones

  摘要：

  Two synthetically useful approaches to 1-substituted anthraquinone derivatives are reported. Application of these methods afforded the following 1-anthraquinyl ethers: n-propyl, n-butyl, n-octyl, n-nonyl, n-hexadecyl, isoamyl, allyl, 2-butenyl, (E)-2-hexenyl, (E)-2-tridecyl, benzyl, phenyl, 4-methylphenyl, 2-butynyl, 2-pentynyl, 2-hexynyl, 3-pentynyl, 3-hexynyl, 3-heptynyl, 3-nonynyl, 4-hexynyl, 4-heptynyl, 5-heptynyl, 5-octynyl, 5-nonynyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-[2-(octadecyloxy)ethoxy]ethoxy]ethyl, 2-(methylthio)ethyl, 2-(1-piperidino)ethyl, and 2-(1-morpholino)ethyl. The results of about 100 nucleophilic substitution reactions (a number were duplicates) are presented. Most of these reactions involve either a new approach, new products, or both. Included are displacements of chloride by alkanols, alkenols, and alkynols. Of the three, only the latter afford acceptable yields of product, although lower yields are observed as the distance between hydroxyl and triple bond increases. Nucleophiles of the type RO(CH2CH2O)nOH proved remarkably effective. Alkynyl ethers and poly(oxyethylene) ethers also proved to be excellent leaving groups. Both alkynols and oligoethylene glycol monoethers were found to be catalysts for the conversion of 1-chloroanthraquinone into 1-anthraquinyl ethers. In an attempt to understand the mechanism of this reaction, solid-state structures of four anthraquinone derivatives have been obtained. These have poly(ethyleneoxy), morpholino, or alkynyl side arms.

  DOI：

  10.1021/jo00025a021

文献信息

• Reduction of 1-substituted anthraquinones to 1- and 4-substituted anthrones
  作者：V. A. Loskutov

  DOI：10.1007/bf02494377

  日期：1997.2

  The regioselectivity of reduction of 1-substituted anthraquinones to 1- or 4-substituted anthrones is determined by both the nature of the substituent and the type of the reducing system used.

  1-取代蒽醌还原为1-或4-取代蒽酮的区域选择性由取代基的性质和所用还原系统的类型决定。
• Effect of substituents on cation-receptor properties of crown-containing 1-hydroxyanthraquinone imines
  作者：A. A. Kudrevatykh、D. A. Neznaeva、T. P. Martyanov、L. S. Klimenko

  DOI：10.1007/s11172-019-2465-8

  日期：2019.3

  Complex formation properties of new crown-containing 1-hydroxyanthraquinone imines with donor and acceptor substituents in the anthraquinone nucleus were studied. The compounds were prepared by photochemical reactions of 4-aminobenzo-15-crown-5-ether with photoactive derivatives of 1-phenoxyanthraquinone. It has been established that the introduction of acceptor substituents causes a shift of the prototropic

  研究了在蒽醌核中具有供体和受体取代基的含新冠1-羟基蒽醌亚胺的复合物形成特性。这些化合物是通过 4-aminobenzo-15-crown-5-ether 与 1-phenoxyanthraquinone 的光活性衍生物的光化学反应制备的。已经确定，受体取代基的引入导致质子互变异构亚胺-烯胺平衡向形成 NH 形式的转变。结果，在复合物形成过程中观察到显着的阳离子诱导的光谱变化。
• Preparation of 1-amino-2-phenoxy-4-hydroxyanthraquinone
  申请人：BASF Aktiengesellschaft

  公开号：US04278606A1

  公开（公告）日：1981-07-14

  In a process for the preparation of 1-amino-2-phenoxy-4-hydroxyanthraquinone by reacting 1-amino-2-halogeno-4-hydroxyanthraquinone with a phenol in an alkaline aqueous medium at an elevated temperature, the improvement that 1-amino-2-chloro-4-hydroxyanthraquinone is reacted in aqueous suspension, at a pH of from 9 to 13 and at from 120.degree. to 150.degree. C., with the phenol in the presence of (a) ammonium salts N.sup..sym. (R).sub.4 A.sup..crclbar., wherein one or more R's are linear or branched C.sub.4 -C.sub.20 -alkyl or C.sub.7 -C.sub.10 -phenylalkyl and the remaining R or R's may also be phenyl or N.sup..sym. (R).sub.3 may be pyridinium, and A.sup..crclbar. is one equivalent of an anion, of (b) ethylene oxide/propylene oxide block copolymers or of (c) oxyethylation products of alkylphenols, of alkenylamines, of alkylamines or of alkanols. A very pure product is obtained, in high yield.

  在制备1-氨基-2-苯氧基-4-羟基蒽醌的过程中，通过在碱性水介质中，在升高的温度下，将1-氨基-2-卤代-4-羟基蒽醌与苯酚反应，改进了方法，即在水悬浮液中以pH为9至13，120℃至150℃的条件下，与苯酚在以下存在下反应：(a)铵盐N.sup..sym.(R).sub.4 A.sup..crclbar.，其中一个或多个R为线性或支链C.sub.4-C.sub.20-烷基或C.sub.7-C.sub.10-苯基烷基，其余的R或R也可以是苯基或N.sup..sym.(R).sub.3可以是吡啶基，A.sup..crclbar.是一个阴离子的当量，或(b)乙氧基/丙氧基嵌段共聚物，或(c)烷基酚、烯基胺、烷基胺或脂肪醇的氧乙烯化产物。可以得到高产率的非常纯净的产物。
• Strain gauge polymer comprising photochromic colorant
  申请人：XEROX CORPORATION

  公开号：US10381134B2

  公开（公告）日：2019-08-13

  A composite manufacture includes an extrudable thermoplastic matrix and a photochromic colorant, the photochromic colorant conferring to the composite a reversible strain-induced color change property. Methods include adding photochromic colorant to an extrudable thermoplastic polymer matrix to form a mixture, heating the mixture to form a composite, the photochromic colorant conferring to the composite a reversible strain-induced color change property. The composite manufactures can be used in cable coatings permitting visual detection of mechanical stresses in a wire based on the reversible strain-induced color change property.

  复合材料制造包括可挤出热塑性基体和光致变色着色剂，光致变色着色剂赋予复合材料可逆的应变诱导变色特性。方法包括将光致变色着色剂添加到可挤出热塑性聚合物基体中以形成混合物，加热混合物以形成复合材料，光致变色着色剂赋予复合材料可逆的应变诱导变色特性。这种复合材料可用于电缆涂层，根据可逆应变诱导变色特性，对电线中的机械应力进行视觉检测。
• DE165728
  申请人：——

  公开号：——

  公开（公告）日：——