25,27-bis(2-hydroxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate | 688330-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-bis(2-hydroxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate
• 英文别名: 25,27-bis(2-hydroxyethoxy)-26,28-bis(1-propoxy)calix[4]arene；25,27-bis(2-hydroxyethoxy)-26,28-bispropoxycalix[4]arene；2-[[27-(2-Hydroxyethoxy)-26,28-dipropoxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]oxy]ethanol；2-[[27-(2-hydroxyethoxy)-26,28-dipropoxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]oxy]ethanol
• CAS: 688330-17-8
• 化学式: C₃₈H₄₄O₆
• 分子量: 596.764
• InChiKey: JUASBDIGTJBJNO-UHFFFAOYSA-N

物化性质

• 沸点：
  797.4±60.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  25,27-bis(2-p-toluenesulfonyloxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate 、 25,27-bis(2-hydroxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以13%的产率得到60,61,69,70-Tetrapropoxy-3,6,9,29,32,35-hexaoxaundecacyclo[35.15.7.711,27.117,21.143,47.154,58.02,49.010,15.023,28.036,41.163,67]heptaconta-1(52),2(49),10(15),11,13,17(69),18,20,23(28),24,26,36(41),37,39,43,45,47(61),50,54(60),55,57,63,65,67(70)-tetracosaene
  参考文献：
  名称：

  Toward Synthetic Tubes for NO₂/N₂O₄:  Design, Synthesis, and Host−Guest Chemistry

  摘要：

  Design of molecular nanotubes is proposed for entrapment and conversion of NO2/N2O4 gases. Synthesis of 1,3-alternate bis-calix[4]arene tube 3 of 5 x 11 Angstrom internal dimensions is presented, and its reversible reactions with NO2/N2O4 in solution are studied. Exposure of 3 to NO2/N2O4 in chlorinated solvents results in the rapid encapsulation of nitrosonium (NO+) cations within its interior. Mono- and dinitrosonium complexes 4 and 5, respectively, were isolated and characterized by UV-vis, FTIR, and H-1 NMR spectroscopies, and also molecular modeling. The NO+ entrapment process is reversible, and addition of water quickly recovered starting tube 3. Encapsulated within the tube NO+ species act as nitrosating agents for secondary amides. These findings open wider perspectives toward NO2/NOx storing and converting materials and also offer a promise for further development of supramolecular chemistry of synthetic nanotubes.

  DOI：

  10.1021/ja0392869
• 作为产物：
  描述：

  25,27-bis(2-p-toluenesulfonyloxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到25,27-bis(2-hydroxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate
  参考文献：
  名称：

  Toward Synthetic Tubes for NO₂/N₂O₄:  Design, Synthesis, and Host−Guest Chemistry

  摘要：

  Design of molecular nanotubes is proposed for entrapment and conversion of NO2/N2O4 gases. Synthesis of 1,3-alternate bis-calix[4]arene tube 3 of 5 x 11 Angstrom internal dimensions is presented, and its reversible reactions with NO2/N2O4 in solution are studied. Exposure of 3 to NO2/N2O4 in chlorinated solvents results in the rapid encapsulation of nitrosonium (NO+) cations within its interior. Mono- and dinitrosonium complexes 4 and 5, respectively, were isolated and characterized by UV-vis, FTIR, and H-1 NMR spectroscopies, and also molecular modeling. The NO+ entrapment process is reversible, and addition of water quickly recovered starting tube 3. Encapsulated within the tube NO+ species act as nitrosating agents for secondary amides. These findings open wider perspectives toward NO2/NOx storing and converting materials and also offer a promise for further development of supramolecular chemistry of synthetic nanotubes.

  DOI：

  10.1021/ja0392869

文献信息

• A procedure for filling calixarene nanotubes
  作者：Valentina Sgarlata、Voltaire G. Organo、Dmitry M. Rudkevich

  DOI：10.1039/b509299j

  日期：——

  Alkyl nitrites readily transfer nitrosonium into calixarene-based synthetic nanotubes thus offering a mild, effective and precise method to fill them.

  亚硝酸烷基酯很容易将硝氮转移到基于杯芳烃的合成纳米管中，因此提供了一种温和，有效和精确的填充方法。
• Long Synthetic Nanotubes from Calix[4]arenes
  作者：Voltaire G. Organo、Valentina Sgarlata、Farhood Firouzbakht、Dmitry M. Rudkevich

  DOI：10.1002/chem.200601545

  日期：2007.5.7

  We report the synthesis and encapsulation properties of long (up to 5 nm) molecular nanotubes 1-4, which are based on calix[4]arenes and can be filled with multiple nitrosonium (NO(+)) ions upon reaction with NO(2)/N(2)O(4) gases. These are among the largest nanoscale molecular containers prepared to date and can entrap up to five guests. The structure and properties of tubular complexes 1(NO(+))(2)-4(NO(+))(5)

  我们报告长（可达5纳米）分子纳米管1-4的合成和封装性能，这些纳米管基于杯[4]芳烃，与NO（2）反应后可充满多个硝基（NO（+））离子）/ N（2）O（4）气体。这些是迄今为止制备的最大的纳米级分子容器，最多可容纳五名客人。管状配合物1（NO（+））（2）-4（NO（+））（5）的结构和性质通过溶液中的UV / Vis，FTIR和（1）H NMR光谱进行了研究，还通过分子建模。NO（+）截留在1（NO（+））（2）-4（NO（+））（5）中是可逆的，添加[18] crown-6可以快速恢复起始管1-4。FTIR和滴定数据表明，较长的试管中NO（+）的结合增强，这可能是由于协同作用所致。所述的纳米管可以用作存储和转化NO（x）的材料，并且还有望进一步发展分子容器的超分子化学。这些发现也为合成碳纳米管作为碳纳米管的替代品的应用开辟了广阔的前景。
• Supramolecular Features of Calixarene-Based Synthetic Nanotubes
  作者：Voltaire G. Organo、Alexander V. Leontiev、Valentina Sgarlata、H. V. Rasika Dias、Dmitry M. Rudkevich

  DOI：10.1002/anie.200500057

  日期：2005.5.13
• Toward Synthetic Tubes for NO₂/N₂O₄:  Design, Synthesis, and Host−Guest Chemistry
  作者：Grigory V. Zyryanov、Dmitry M. Rudkevich

  DOI：10.1021/ja0392869

  日期：2004.4.1

  Design of molecular nanotubes is proposed for entrapment and conversion of NO2/N2O4 gases. Synthesis of 1,3-alternate bis-calix[4]arene tube 3 of 5 x 11 Angstrom internal dimensions is presented, and its reversible reactions with NO2/N2O4 in solution are studied. Exposure of 3 to NO2/N2O4 in chlorinated solvents results in the rapid encapsulation of nitrosonium (NO+) cations within its interior. Mono- and dinitrosonium complexes 4 and 5, respectively, were isolated and characterized by UV-vis, FTIR, and H-1 NMR spectroscopies, and also molecular modeling. The NO+ entrapment process is reversible, and addition of water quickly recovered starting tube 3. Encapsulated within the tube NO+ species act as nitrosating agents for secondary amides. These findings open wider perspectives toward NO2/NOx storing and converting materials and also offer a promise for further development of supramolecular chemistry of synthetic nanotubes.