4,4',5,5'-Tetraaminodibenzo-18-crown-6 | 122942-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4',5,5'-Tetraaminodibenzo-18-crown-6
• 英文别名: 6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine-2,3,13,14-tetraamine；2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(22),9(14),10,12,23,25-hexaene-11,12,24,25-tetramine
• CAS: 122942-39-6
• 化学式: C₂₀H₂₈N₄O₆
• 分子量: 420.466
• InChiKey: VHKNDNAYRKYOFY-UHFFFAOYSA-N

物化性质

• 沸点：
  702.0±60.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  二(2-吡啶基)乙二酮 、 4,4',5,5'-Tetraaminodibenzo-18-crown-6 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以30%的产率得到2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline
  参考文献：
  名称：

  Ratiometric and Selective Fluorescent Sensor for Zn²⁺ as an “Off–On–Off” Switch and Logic Gate

  摘要：

  A new chemosensor, 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline (1), containing 2,3-bis(pyridin-2-yl)quinoxaline and crown ether moieties, has been designed and found to be a ratiometric and selective fluorescent detector of Zn2+ over a wide range of tested metal ions. The addition of Zn2+ to the solution of 1 in acetonitrile induced the formation of a 1:2 ligand-metal complex, 1-Zn2+, which exhibits a remarkable enhanced fluorescent emission centered at 460 nm, with the disappearance of the fluorescent emission of 1 centered at 396 nm due to the mechanism of internal charge transfer. In contrast, the presence of K+ results in the fluorescence quenching of 1 and 1-Zn2+ through the photoinduced electron-transfer mechanism. These results demonstrate that 1 can perform as not only an INHIBIT logic gate but also an "off-on-off" molecular switch triggered by Zn2+ and K+. The structure of complex 1-Zn2+ has been characterized by single-crystal X-ray crystallography, mass spectrometry, and H-1 NMR titration experiments. Density functional theory calculation results on 1 and the 1-Zn2+ complex are well consistent with the experimental results.

  DOI：

  10.1021/ic300738e
• 作为产物：
  描述：

  二苯并-18-冠醚-6 在 palladium on activated charcoal 氢气 、 硝酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 4,4',5,5'-Tetraaminodibenzo-18-crown-6
  参考文献：
  名称：

  Lipophilic Metal−Salicylideneimine−Crown Ether Hybrids — Ditopic Carriers in the Facilitated Transport of Amphiphilic Molecules Across Bulk Liquid Membranes

  摘要：

  DOI：

  10.1002/1099-0682(200103)2001:3<761::aid-ejic761>3.3.co;2-q

文献信息

• Crown ether functionalized texaphyrin monomers and dimers
  作者：Christian Preihs、Darren Magda、Jonathan L. Sessler

  DOI：10.1142/s108842461100315x

  日期：2011.7

  The synthesis and characterization of two 18-crown-6 functionalized analogues of an extensively studied gadolinium texaphyrin derivative, motexafin gadolinium (1, MGd), are reported. These are the monomeric and dimeric species, compounds 2 and 3, respectively. Both crown ether functionalized species proved to be stable at physiological pH and revealed distinct shifts in the UV spectrum when treated with sodium-, potassium-, ammonium- or zinc(II)-salts. Zinc(II) is believed to play a major role regulating apoptosis mechanisms in cancerous cells. Therefore, cytotoxicity studies of 2 and 3 were carried out using the Ramos cell line in the presence and absence of zinc(II).

  本研究报道了一种经过广泛研究的钆特沙芬衍生物--莫特沙芬钆（1，MGd）的两种 18 冠 6 官能化类似物的合成和表征。它们分别是单体和二聚体化合物 2 和 3。事实证明，这两种冠醚官能化物种在生理 pH 值条件下都很稳定，并且在钠盐、钾盐、铵盐或锌盐（II）处理时，紫外光谱会发生明显的偏移。锌（II）被认为在调节癌细胞凋亡机制方面发挥着重要作用。因此，我们使用拉莫斯细胞系，在锌盐（II）存在和不存在的情况下，对 2 和 3 进行了细胞毒性研究。
• Lipophilic Metal−Salicylideneimine−Crown Ether Hybrids — Ditopic Carriers in the Facilitated Transport of Amphiphilic Molecules Across Bulk Liquid Membranes
  作者：Jay??D. Pike、Dell??T. Rosa、Dimitri Coucouvanis

  DOI：10.1002/1099-0682(200103)2001:3<761::aid-ejic761>3.3.co;2-q

  日期：2001.3
• Crown-Linked Porphyrin Systems
  作者：Sandhya A. Duggan、Gary Fallon、Steven J. Langford、Vei-Lin Lau、Jacqueline F. Satchell、Michael N. Paddon-Row

  DOI：10.1021/jo001700p

  日期：2001.6.1
• Ovchinnikova; Fedorova; Rusinov, Russian Journal of Organic Chemistry, 1999, vol. 35, # 7, p. 1082 - 1085
  作者：Ovchinnikova、Fedorova、Rusinov

  DOI：——

  日期：——
• Ratiometric and Selective Fluorescent Sensor for Zn²⁺ as an “Off–On–Off” Switch and Logic Gate
  作者：Ya-Ping Li、Hua-Rong Yang、Qiang Zhao、Wei-Chao Song、Jie Han、Xian-He Bu

  DOI：10.1021/ic300738e

  日期：2012.9.17

  A new chemosensor, 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline (1), containing 2,3-bis(pyridin-2-yl)quinoxaline and crown ether moieties, has been designed and found to be a ratiometric and selective fluorescent detector of Zn2+ over a wide range of tested metal ions. The addition of Zn2+ to the solution of 1 in acetonitrile induced the formation of a 1:2 ligand-metal complex, 1-Zn2+, which exhibits a remarkable enhanced fluorescent emission centered at 460 nm, with the disappearance of the fluorescent emission of 1 centered at 396 nm due to the mechanism of internal charge transfer. In contrast, the presence of K+ results in the fluorescence quenching of 1 and 1-Zn2+ through the photoinduced electron-transfer mechanism. These results demonstrate that 1 can perform as not only an INHIBIT logic gate but also an "off-on-off" molecular switch triggered by Zn2+ and K+. The structure of complex 1-Zn2+ has been characterized by single-crystal X-ray crystallography, mass spectrometry, and H-1 NMR titration experiments. Density functional theory calculation results on 1 and the 1-Zn2+ complex are well consistent with the experimental results.