2,3-bis(bromomethyl)-1,4-dihydroxyanthracene-9,10-dione | 77422-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-bis(bromomethyl)-1,4-dihydroxyanthracene-9,10-dione
• CAS: 77422-59-4
• 化学式: C₁₆H₁₀Br₂O₄
• 分子量: 426.061
• InChiKey: PKHIPHBPAMPVCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis(bromomethyl)-1,4-dihydroxyanthracene-9,10-dione 在 硫酸 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  3-(Acyloxy)-3-buten-2-ones as dienophiles in anthracyclinone synthesis. An efficient route to 4-demethoxy-7-deoxydaunomycinone derivatives

  摘要：

  DOI：

  10.1021/jo00342a005
• 作为产物：
  描述：

  2,3-二甲基氢醌 在 盐酸 、 三氯化铝 、 过氧化氢苯甲酰 、 溴 、 sodium chloride 作用下， 以 四氯乙烯 为溶剂， 反应 22.03h， 生成 2,3-bis(bromomethyl)-1,4-dihydroxyanthracene-9,10-dione
  参考文献：
  名称：

  Simple o-quinodimethane route to (.+-.)-4-demethoxydaunomycinone

  摘要：

  DOI：

  10.1021/ja00398a020

文献信息

• Synthesis and characterisation of C60 derivatives containing functionalised anthraquinone groups and an unusual fullerene-stabilised cation
  作者：Wolfgang Bidell、Richard G Compton、John C Eklund、Malcolm L.H Green、Thomas O Rebbitt、Adam H.H Stephens

  DOI：10.1016/s0022-328x(98)00436-7

  日期：1998.7

  ortho-anthraquinonedimethane dienophiles prepared in situ from 1,4-dihydroxy-2,3-bis(bromomethyl)-anthraquinone and 1,4-dimethoxy-2,3-bis(bromomethyl)anthraquinone respectively react with the fullerene C60 to give the anthraquinone derivatives: dihydroxy-anthraquinone-C60 and dimethoxy-anthraquinone-C60. The former compound with sodium butoxide and 15-crown-5 gives the bis(sodium-15-crown-5)dioxo-anthraquinone-C60

  的邻位由1,4-二羟基-2,3-双（溴甲基）原位制备-anthraquinonedimethane亲二烯体-蒽醌和1,4-二甲氧基-2,3-双（溴甲基）蒽醌分别与富勒烯C反应60，得到蒽醌衍生物：二羟基蒽醌-C 60和二甲氧基蒽醌-C 60。与丁醇钠和15-冠5的前一种化合物得到双（钠-15-冠-5）二氧杂蒽醌-C 60。所述二甲氧基蒽醌-C 60分发生反应，以[Ru（PPH 3）2（NO）CL]，以形成双加合物[ η 2 - （二甲氧基-蒽醌-C 60）]的[Ru（PPH 3）2（NO）Cl]}。已经通过循环伏安法研究了二羟基和二甲氧基蒽醌-C 60衍生物的电化学，与1,4-二羟基-2,3-二甲基蒽醌相反，化合物二羟基-蒽醌-C 60显示两个独立的一个电子在较低电位下的氧化强烈表明富勒烯稳定阳离子的一个相对罕见的例子。
• Influence of Silver Nanoparticles on 2,3-Bis(Chloromethyl)Anthracene-1,4,9,10-Tetraone
  作者：Mahalingam Umadevi、N. A. Sridevi、A. S. Sharmila、Beulah J. M. Rajkumar、M. Briget Mary、P. Vanelle、T. Terme、O. Khoumeri

  DOI：10.1007/s10895-009-0533-4

  日期：2010.1

  Size effect of silver nano particles on the photophysical properties of 2,3-bis(chloromethyl)anthracene-1,4,9,10-tetraone (BCMAT) have been investigated using optical absorption and fluorescence emission techniques. Silver NPs of different sizes have been prepared by two different methods. Quenching of fluorescence of BCMAT has been found to increase with decrease in the size of the silver NPs. Stern–Volmer quenching constants have also been calculated.

  利用光学吸收和荧光发射技术研究了纳米银粒子的尺寸对 2,3-双（氯甲基）蒽-1,4,9,10-四酮（BCMAT）光物理性质的影响。通过两种不同的方法制备了不同大小的银 NPs。研究发现，BCMAT 的荧光淬灭随银 NPs 尺寸的减小而增加。此外，还计算了斯特恩-沃尔默淬灭常数。
• Surface-Enhanced Infrared Spectral Investigations of 2,3-Bis(chloromethyl)anthracene-1,4,9,10-tetraone on Copper Nanoparticles
  作者：M. Umadevi、S. Jeyaseeli、M. Anuratha、P. Vanelle、T. Terme

  DOI：10.1080/00387010.2011.635173

  日期：2012.9

  Surface-enhanced infrared (IR) absorption spectroscopic technique has been employed to investigate the orientation of 2,3-bis(chloromethyl) anthracene-1,4,9,10-tetraone (BCMAT) on copper nanoparticles (NPs). Copper NPs have been prepared by the chemical reduction method. The observed ring stretching modes show higher downshifts, broader bandwidths, and higher enhancement. The observed features in out-of-plane and in-plane CH deformation modes indicate that the BCMAT molecules may be adsorbed in a "flat-on" orientation on the copper NPs. The observed lower enhancement factor of the in-plane C=O deformation mode and C=O stretching mode and the higher enhancement factor of out-of-plane C=O deformation mode elucidate that the BCMAT molecules are adsorbed on the copper NPs in a "flat-on" orientation. All these observations show that BCMAT is adsorbed on copper NPs through the pi-anthraquinone ring system in a "flat-on" orientation.
• 3-(Acyloxy)-3-buten-2-ones as dienophiles in anthracyclinone synthesis. An efficient route to 4-demethoxy-7-deoxydaunomycinone derivatives
  作者：Robert J. Ardecky、Domingo Dominguez、Michael P. Cava

  DOI：10.1021/jo00342a005

  日期：1982.1
• Simple o-quinodimethane route to (.+-.)-4-demethoxydaunomycinone
  作者：Francis A. J. Kerdesky、Robert J. Ardecky、M. V. Lakshmikantham、Michael P. Cava

  DOI：10.1021/ja00398a020

  日期：1981.4