11-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)undecanamide | 790229-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)undecanamide
• CAS: 790229-47-9
• 化学式: C₂₅H₂₈BrNO₃
• 分子量: 470.406
• InChiKey: HVQRPYQTZMALSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  11-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)undecanamide 、 5-(4-hydroxyphenyl)-10,15,20-tri(p-tolyl)porphyrin 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以87%的产率得到
  参考文献：
  名称：

  The photoinduced electron transference of porphyrin–anthraquinone dyads bridged with different lengths of links

  摘要：

  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.

  DOI：

  10.1016/j.saa.2010.11.006
• 作为产物：
  描述：

  11-溴十一酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 11-bromo-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)undecanamide
  参考文献：
  名称：

  The photoinduced electron transference of porphyrin–anthraquinone dyads bridged with different lengths of links

  摘要：

  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.

  DOI：

  10.1016/j.saa.2010.11.006

文献信息

• DNA-binding and photocleavage properties of cationic porphyrin–anthraquinone hybrids with different lengths of links
  作者：Ping Zhao、Lian-Cai Xu、Jin-Wang Huang、Bo Fu、Han-Cheng Yu、Wei-Hong Zhang、Jian Chen、Jun-Hua Yao、Liang-Nian Ji

  DOI：10.1016/j.bioorg.2008.08.002

  日期：2008.12

  Four cationic porphyrin-anthraquinone (Por-AQ) hybrids differing in lengths of flexible alkyl linkage, 5-[4-(1-N-anthraquinonon-yl)-L-oxophenyl]-10,15,20-tris(N-methylpyridinium-4-yl)p orphyrin triiodide, (L = acetyl, pentanoyl, octanoyl, undecanoyl, designed as [AQATMPyP]I3, [AQPTMPyP]I3, [AQOTMPyP]I3 and [AQUTMPyP]I3, respectively, see Fig. 1), were synthesized and their interactions with DNA were

  四个阳离子卟啉-蒽醌（Por-AQ）杂化物，其柔性烷基键长度不同，5- [4-（1-N-蒽醌基-基）-L-氧代苯基] -10,15,20-三（N-甲基吡啶鎓） -4-基）p卟啉三碘化物（分别为[AQATMPyP] I3，[AQPTMPyP] I3，[AQOTMPyP] I3和[AQUTMPyP] I3，分别设计为L =乙酰基，戊酰基，辛酰基，十一烷酰基，见图1），合成并研究了它们与DNA的相互作用。光谱，变性和粘度测量的结果表明，[AQATMPyP] I3通过非插入模式与DNA结合，而具有较长连接的其他三个杂种通过双插入模式结合。进行了溴化乙锭（EB）竞争实验以确定这些化合物与CT DNA的结合常数（Kb），[AQPTMPyP] I3显示了这些杂种中最大的Kb。