2-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide | 14226-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide
• 英文别名: 2-bromo-N-(9,10-dioxoanthracen-1-yl)acetamide
• CAS: 14226-37-0
• 化学式: C₁₆H₁₀BrNO₃
• 分子量: 344.164
• InChiKey: MAUPEUPHEPMTIE-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  576.6±50.0 °C(Predicted)
• 密度：
  1.676±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-三氯苯酚 、 2-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以85%的产率得到N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-(2,4,6-trichlorophenoxy)acetamide
  参考文献：
  名称：

  1-(苯基硫基/苯氧基)-3H-萘并[1,2,3-de]喹啉-2,7-二酮的合成

  摘要：

  设计了一种方便的方法，通过 2-溴-N 的缩合，首次以高产率合成 1-(苯硫基/苯氧基)-3H-萘并[1,2,3-de]喹啉-2,7-二酮类似物-(9,10-二氧-二氢-蒽-1-基)-乙酰胺与苯硫醇/苯酚使用碳酸钾。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:221–227, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20399

  DOI：

  10.1002/hc.20399
• 作为产物：
  描述：

  溴乙酰氯 、 氨基-9,10-蒽二酮 以 苯 为溶剂， 反应 7.0h， 以74%的产率得到2-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide
  参考文献：
  名称：

  Litvinova, L. A.; Lyakhov, S. A.; Andronati, S. A., Pharmaceutical Chemistry Journal, 1998, vol. 32, # 12, p. 637 - 640

  摘要：

  DOI：

文献信息

• Optical and electrochemical properties of heteroditopic ion receptors derived from crown ether-based calix[4]arene with amido-anthraquinone pendants
  作者：Benjamat Chailap、Thawatchai Tuntulani

  DOI：10.1039/c2ob00048b

  日期：——

  Two heteroditopic receptors based on a calix[4]arene crown ether containing amidoanthraquinone pendants in cone and 1,3-alternate conformations (1 and 2, respectively) were synthesized. Photophysical properties of 1 and 2 were studied by UV-vis and fluorescence spectrophotometry in dried CH3CN. Both 1 and 2 showed the highest sensitivity towards F− through the appearance of a new charge transfer band at 500 nm and the enhancement of the emission spectra at λem = 542 nm and 528 nm respectively. Interestingly, in the presence of K+, the fluorescence intensity of 1 at 542 nm increased around 2 fold compared to that in the absence of K+ upon addition of F−, while this phenomenon was not observed in the case of receptor 2. Cyclic voltammograms of receptors 1 and 2 showed two consecutive one-electron reversible waves in 40% v/v CH3CN in CH2Cl2, corresponding to two single-electron reductions to give mono- and dianions species at E1/2I = −1.21 V and E1/2II = −1.66 V as well as E1/2I = −1.25 V and E1/2II = −1.71 V, respectively. H2PO4− gave remarkable potential shifts (ca. 200 mV) of the second reduction waves (E1/2II) of both free 1 and 2. In the presence of K+, only receptor 1 gave remarkable potential shifts in its redox wave II upon adding F− and AcO−. Therefore, receptors 1 and 2 exhibited dual sensing modes by fluorescence spectrophotometry and cyclic voltammetry. The topology of ligands also played an important role in cooperative binding properties of heteroditopic receptor 1 possessing a closer distance between a cation and an anion binding. On the other hand, the two ion binding sites of receptor 2 were separated by a longer distance and did not support the cooperative binding. This resulted in the abstraction of K+ from receptor 2 upon addition of anions.

  我们合成了两种基于钙[4]炔冠醚的异位受体，它们含有锥构型和 1,3 邻构型的氨基蒽醌垂饰（分别为 1 和 2）。在干燥的 CH3CN 中，通过紫外-可见分光光度法和荧光分光光度法研究了 1 和 2 的光物理特性。通过在 500 纳米波长处出现新的电荷转移带，以及分别在 λem = 542 纳米波长和 528 纳米波长处增强发射光谱，1 和 2 对 F- 显示出最高的灵敏度。有趣的是，在 K+ 存在的情况下，加入 F- 后，1 在 542 nm 处的荧光强度比 K+ 不存在时增加了约 2 倍，而受体 2 则没有观察到这种现象。受体 1 和 2 的循环伏安图在 40% v/v CH3CN in CH2Cl2 中显示出两个连续的单电子可逆波，分别对应于两个单电子还原，在 E1/2I = -1.21 V 和 E1/2II = -1.66 V 以及 E1/2I = -1.25 V 和 E1/2II = -1.71 V 时产生单离子和双离子。H2PO4- 使游离 1 和游离 2 的第二还原波（E1/2II）发生显著的电位偏移（约 200 mV）。在 K+ 存在的情况下，只有受体 1 在加入 F- 和 AcO- 后其氧化还原波 II 发生了显著的电位移动。因此，通过荧光分光光度法和循环伏安法，受体 1 和 2 表现出双重感应模式。配体的拓扑结构对异位受体 1 的协同结合特性也起着重要作用，它具有阳离子和阴离子之间更近的结合距离。另一方面，受体 2 的两个离子结合位点之间的距离较长，不支持协同结合。这导致受体 2 在加入阴离子时会抽取 K+。
• The photoinduced electron transference of porphyrin–anthraquinone dyads bridged with different lengths of links
  作者：Ping Zhao、Jin-Wang Huang、Lian-Cai Xu、Li Ma、Liang-Nian Ji

  DOI：10.1016/j.saa.2010.11.006

  日期：2011.1

  The photoinduced electron transference (PET) interaction in porphyrin containing donor-acceptor (D-A) molecules is of great importance in nature and a significant part of the PET research has been devoted to the study of its mechanism ("through-space" or "through-bond") in these decades. Herein we synthesized a series of covalently linked porphyrin-anthraquinone dyads (Por-C(n)-AQ) bridged with flexible alkoxy chains at different lengths (n = 1, 4, 10) and investigated their intramolecular PET using a combination of electronic absorption, steady-state fluorescence and decayed luminescence spectra. The experimental results show that the PET efficiency depends on the length of the flexible linkage between the porphyrin and anthraquinone moieties. Meanwhile, theoretical calculation applying the density functional theory (OFT) was also carried out to give the frontier orbital distribution and the optimized structures of these dyads. It is found that the orientation of the dyad with high PET efficiency is disadvantageous to pi-pi interaction. Thus, the PET of these dyads seemingly is best compatible with a "through-bond" (superexchange) mechanism. (c) 2010 Elsevier B.V. All rights reserved.
• Selective fluoride ion recognition by a thiacalix[4]arene receptor containing N-(4-nitrophenyl)acetamide and 1-amidoanthraquinone fragments
  作者：Alena A. Vavilova、Roman V. Nosov、Ivan I. Stoikov

  DOI：10.1016/j.mencom.2016.11.016

  日期：2016.11

  New derivatives of thiacalix[4]arene, tri- and tetrasubstituted at the lower rim by N-(4-nitrophenyl)acetamide and 1-amidoanthraquinone fragments were synthesized. Their ability for recognition and binding of some anions (F-, Cl-, Br-, I-, MeCO2-, H2PO4-, NO3-) was examined by UV spectroscopy, and a selective receptor for fluoride ion giving a 1:1 complex was invented.
• Chromofluorescent Probes for Selective Detection of Fluoride and Acetate Ions
  作者：Subodh Kumar、Vijay Luxami、Ashwani Kumar

  DOI：10.1021/ol802352j

  日期：2008.12.18

  Chromofluorescent probe 2 has been developed for selective and ratiometric estimation of F- (CH3CN) ions. The presence of a lipophilic dodecyl appendage at imidazolium nitrogen in 3 successfully allows the selective determination of AcO- ions in protic (CHCl3-MeOH, 1:1) solvent.
• US7173026B2
  申请人：——

  公开号：US7173026B2

  公开（公告）日：2007-02-06