N,N′-bis(4-(pyridin-4-ylethynyl)phenyl)terephthalamide | 1447972-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N′-bis(4-(pyridin-4-ylethynyl)phenyl)terephthalamide
• 英文别名: 1-N,4-N-bis[4-(2-pyridin-4-ylethynyl)phenyl]benzene-1,4-dicarboxamide
• CAS: 1447972-06-6
• 化学式: C₃₄H₂₂N₄O₂
• 分子量: 518.574
• InChiKey: DRVXLMYZTPMECV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [Ru₂(p-cymene)₂(2,5-dioxido-1,4-benzoquinonato)Cl₂] 、 N,N′-bis(4-(pyridin-4-ylethynyl)phenyl)terephthalamide 、 silver trifluoromethanesulfonate 以 甲醇 、 硝基甲烷 为溶剂， 反应 14.0h， 以90%的产率得到[Ru₂(cymene)₂(2,5-dihydroxy-1,4-benzoquinonato)Cl₂]₂(N,N′-bis[4-(pyridin-4-ylethynyl)phenyl]terephthalamide)₂(triflate)₄
  参考文献：
  名称：

  Synthesis and Characterization of Self-Assembled Nanoscopic Metallarectangles Capable of Binding Fullerenes with Size-Selective Responses

  摘要：

  Two new metallarectangles, 4 and 5, were obtained from the self assembly of areneruthenium-based molecular clips 2 and 3 with a new dipyridyl donor ligand 1 containing a diamide core and ethynyl spacers. The metallarectangles were characterized by multinuclear NMR, electrospray ionization mass spectrometry, and UV-vis spectroscopy, and the molecular structure of 4 was unambiguously determined by single crystal X-ray diffraction analysis. Because of the presence of an extended pi-electron aromatic surface, the tetracene-containing molecular rectangle 5 was capable of binding C-60 and C-70 fullerenes as quantified by UV-vis, emission, and H-1 NMR experiments, providing an example of a supramolecular host capable of recognizing large guest molecules

  DOI：

  10.1021/ic401685s
• 作为产物：
  描述：

  N,N′-bis(4-iodophenyl)terephthalamide 、 4-ethynylpyridine hydrochloride 在 三乙胺 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以77%的产率得到N,N′-bis(4-(pyridin-4-ylethynyl)phenyl)terephthalamide
  参考文献：
  名称：

  Synthesis and Characterization of Self-Assembled Nanoscopic Metallarectangles Capable of Binding Fullerenes with Size-Selective Responses

  摘要：

  Two new metallarectangles, 4 and 5, were obtained from the self assembly of areneruthenium-based molecular clips 2 and 3 with a new dipyridyl donor ligand 1 containing a diamide core and ethynyl spacers. The metallarectangles were characterized by multinuclear NMR, electrospray ionization mass spectrometry, and UV-vis spectroscopy, and the molecular structure of 4 was unambiguously determined by single crystal X-ray diffraction analysis. Because of the presence of an extended pi-electron aromatic surface, the tetracene-containing molecular rectangle 5 was capable of binding C-60 and C-70 fullerenes as quantified by UV-vis, emission, and H-1 NMR experiments, providing an example of a supramolecular host capable of recognizing large guest molecules

  DOI：

  10.1021/ic401685s

文献信息

• Coordination-Driven Self-Assembly and Anticancer Potency Studies of Arene–Ruthenium-Based Molecular Metalla-Rectangles
  作者：Anurag Mishra、Yong Joon Jeong、Jae-Ho Jo、Se Chan Kang、Hyunuk Kim、Ki-Whan Chi

  DOI：10.1021/om401042m

  日期：2014.3.10

  The two new large molecular metalla-rectangles 6 and 8 were obtained by the reaction of the two different arene-ruthenium acceptors [Ru-2(p-cymene)(2)(mu-eta(4)-C2O4)Cl-2] (2) and [Ru-2(p-cymene)(2)(donq)(Cl)(2)] (donq = 5,8-dioxido-1,4-naphthoquinonato) (4) with a symmetrical N,N'-bis(4-(pyridin-4-ylethynyl)phenyl)-terephthalamide (1) donor ligand. Both metalla-rectangles were isolated in good yields as triflate salts and were characterized by multinuclear NMR, ESI-MS, and UV-vis spectroscopy. X-ray crystallography of 6 confirmed a molecular metalla-rectangle. The cytotoxicities of metalla-rectangles 6-9 were established in SK-hep-1 (liver cancer), AGS (gastric cancer), and HCT-15 (colorectal cancer) human cancer cell lines. The cytotoxicity of metalla-rectangle 8 was found to be considerably stronger against all cancer cell lines, even much more effective than the well-known anticancer drugs doxorubicin and cisplatin. In addition, expressions of APC and p53, colorectal cancer suppressor genes, were significantly increased following exposure to the metalla-rectangle 8.
• Synthesis and Characterization of Self-Assembled Nanoscopic Metallarectangles Capable of Binding Fullerenes with Size-Selective Responses
  作者：Anurag Mishra、Hyunji Jung、Min Hyung Lee、Myoung Soo Lah、Ki-Whan Chi

  DOI：10.1021/ic401685s

  日期：2013.8.5

  Two new metallarectangles, 4 and 5, were obtained from the self assembly of areneruthenium-based molecular clips 2 and 3 with a new dipyridyl donor ligand 1 containing a diamide core and ethynyl spacers. The metallarectangles were characterized by multinuclear NMR, electrospray ionization mass spectrometry, and UV-vis spectroscopy, and the molecular structure of 4 was unambiguously determined by single crystal X-ray diffraction analysis. Because of the presence of an extended pi-electron aromatic surface, the tetracene-containing molecular rectangle 5 was capable of binding C-60 and C-70 fullerenes as quantified by UV-vis, emission, and H-1 NMR experiments, providing an example of a supramolecular host capable of recognizing large guest molecules