7,16-bis(tetrafluoropyridin-4-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane | 849544-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7,16-bis(tetrafluoropyridin-4-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• 英文别名: N,N'-bis(tetrafluoropyridyl)diaza-18-crown-6
• CAS: 849544-33-8
• 化学式: C₂₂H₂₄F₈N₄O₄
• 分子量: 560.444
• InChiKey: IEXAIOCHPJRLNV-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C(Solv: methanol (67-56-1))
• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.18
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  7,16-bis(tetrafluoropyridin-4-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 、 lead(II) perchlorate trihydrate 以 二氯甲烷 、 丙酮 为溶剂， 生成 diaqua[N,N'-bis(tetrafluoropyridyl)diaza-18-crown-6]lead(II) perchlorate
  参考文献：
  名称：

  The first example of a complex of N-perfluoroarylated azacrown ether: The crystal structure of diaqua{N,N′-bis(tetrafluoropyridyl)diaza-18-crown-6}lead(II) perchlorate

  摘要：

  Complex formation of lead( II) perchlorate with N, N '-diaryldiaza- 18-crown-6 ( aryl = C 6 H 5, 4- MeOC6 H-4, 4- C-5 F-4 N) has been studied. The stability of the complexes decreases with an increase in the electron-withdrawing character of the aryl substituent in the series (log beta, methanol): 4-MeOC6 H-4 (4.7), C-6 H-5 (2.7), 4-C-5 F-4 N (< 0 in methanol, 0.9 in acetone- d(6)). The dihydrate complex of lead( II) perchlorate with N,N'-bis( tetrafluoropyridyl) diaza-18-crown- 6 (L) [ Pb (L)( H2O)(2)](ClO4)(2) has been studied by X-ray crystallography. The crystals are monoclinic, a = 9.260(2) angstrom, b = 16.986(2) angstrom, c = 21.620(3) angstrom, beta = 96.01(2)degrees, V = 3381.9(9) angstrom(3), Z = 4, space group P2(1)/n, R = 0.0449 for 5126 reflections with I > 2 sigma(I). In the complex cation [Pb (L)( H2O)(2)] (2+), the coordination geometry of the metal atom is determined by partial delocalization of the lone pair. The Pb atom is asymmetrically bound to four oxygen atoms of substituted diaza-18-crown-6 and two oxygen atoms of water molecules (Pb-O, 2.450-2.726 angstrom). The CN of the metal atom is completed to ten by two nitrogen atoms of the macrocycle and two ortho fluorine atoms of two tetrafluoropyridyl substituents of the ligand L at longer distances (Pb-N, 2.978 and 3.108 angstrom; Pb-F, 2.890 and 3.123 angstrom).

  DOI：

  10.1134/s003602360707008x
• 作为产物：
  描述：

  五氟吡啶 、 二氮杂18-冠醚-6 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到7,16-bis(tetrafluoropyridin-4-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  参考文献：
  名称：

  N-aryl-and N-vinyldiaza-18-crown-6: Synthesis and complexing ability

  摘要：

  The nucleophilic aromatic and vinyl substitution using diaza-18-crown-6 as nucleophile afforded a number of its N,N'-diaryl-[aryl = 2,4-(NO2)(2)C6H3, 4-C5F4N, 4-CF3C6F4] and N,N'-dialkenyl-substituted derivatives [alkenyl = PhC(O)CH=CH, MeOCOCH=CH, (EtO2C)(2)C=C(Ph), etc.]. Arylation of diaza-18-crown-6 with nonactivated aryl bromides, such as 4-Me2NC6H4Br, 4-MeOC6H4Br, C6H5Br, and 4-CF3C6H4Br, was effected under catalysis by palladium complexes. N,N'-Diaryldiaza-18-crowns-6 having electron-acceptor substituents in the aromatic rings turned out to be incapable of fanning complexes with metal cations, while their analogs containing electron-donor para-methoxy and para-dimethylamino groups gave complexes with barium perchlorate.

  DOI：

  10.1134/s1070428006030171