1-(benzyloxy)anthracene-9,10-dione | 79352-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(benzyloxy)anthracene-9,10-dione
• 英文别名: 1-benzyloxy-9,10-anthraquinone；1-(Benzyloxy)anthraquinone；1-phenylmethoxyanthracene-9,10-dione
• CAS: 79352-68-4
• 化学式: C₂₁H₁₄O₃
• 分子量: 314.34
• InChiKey: QDXBUEMSDUAJKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C(Solv: methanol (67-56-1))
• 沸点：
  522.4±39.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-(benzyloxy)anthracene-9,10-dione 在 三氟乙酸 作用下， 反应 1.0h， 以77%的产率得到1-羟基蒽醌
  参考文献：
  名称：

  蒽醌的新途径

  摘要：

  衍生自邻苯二甲酸酯3位的锂盐与芳烃反应形成加合物，在空中氧化后可产生中等至良好收率的蒽醌。取代的邻苯二甲酸酯和芳烃也参与该一般反应。不对称取代的芳烃的添加显示了区域选择性，而新的通用方法可用于邻苯二甲酰亚胺扩展了该反应的范围。

  DOI：

  10.1039/p19810002120
• 作为产物：
  描述：

  1-氯蒽醌 、 苯甲醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以22%的产率得到1-(benzyloxy)anthracene-9,10-dione
  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

• Photochemistry of 1,<i>n</i>-Dibenzyloxy-9,10-anthraquinones
  作者：Saurav J. Sarma、Paul B. Jones

  DOI：10.1021/jo100650u

  日期：2010.6.4

  favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C−O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance

  研究了一系列具有多个苄氧基取代基的9,10-蒽醌的光化学性质。在极性溶剂中，预期的Blankespoor氧化裂解反应是主要的反应途径，但在大多数情况下，观察到一些次要产物。在非极性溶剂中，这些次要产物的丰度急剧增加。观察到四种类型的产物，其有利的反应路径发生了变化，蒽醌上的取代发生了微小变化。几种类型的产品需要裂解苄氧基上的C-O键，并且显然遵循光克莱森型机理。其他涉及预期的1，5-双自由基，但不表现出通常在布兰克斯珀型反应中观察到的单电子转移。
• PHASE-TRANSFER CATALYZED ALKYLATION OF HYDROXY 9,10-ANTHRAQUINONES
  作者：Douglas R. Robello、Teresa D. Eldridge、Edward J. Urankar

  DOI：10.1080/00304949909355734

  日期：1999.8
• DODSWORTH D. J.; CALCAGNO M.-P.; EHRMANN E. U.; DEVADAS B.; SAMMES P. G., J. CHEM. SOC. PERKIN TRANS. PART 1, 1981, NO 7, 2120-2124
  作者：DODSWORTH D. J.、 CALCAGNO M.-P.、 EHRMANN E. U.、 DEVADAS B.、 SAMMES P. G.

  DOI：——

  日期：——
• SEGUCHI, KAZUYOSHI;OZASA, AKIKO, YUKAGAKU, 1982, 31, N 9, 609-611
  作者：SEGUCHI, KAZUYOSHI、OZASA, AKIKO

  DOI：——

  日期：——
• METHOD OF GENOME-WIDE DIRECT IDENTIFICATION OF ELECTROPHILE-SENSING TARGETS
  申请人：Cornell University

  公开号：US20190265250A1

  公开（公告）日：2019-08-29

  The present invention relates to a method for identifying endogenous first responder protein-cysteines. Methods for screening candidate compounds suitable for regulating NF-kB signaling and the DNA damage response pathway are also disclosed.