25,27-bis(1-propyloxy)calix[4]arene azacrown-5 | 268746-67-4

• 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(1-propyloxy)calix[4]arene azacrown-5
• 英文别名: 40,41-Dipropoxy-3,6,12,15-tetraoxa-9-azahexacyclo[15.15.7.123,27.134,38.02,29.016,21]hentetraconta-1(32),2(29),16(21),17,19,23,25,27(41),30,34(40),35,37-dodecaene
• CAS: 268746-67-4；334905-17-8
• 化学式: C₄₂H₅₁NO₆
• 分子量: 665.87
• InChiKey: OJORURRJDPVWRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(溴甲基)芘 、 25,27-bis(1-propyloxy)calix[4]arene azacrown-5 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以21%的产率得到N-(1-pyrenemethyl)-25,27-bis(1-propyloxy)calix[4]arene azacrown-5
  参考文献：
  名称：

  -武装的杯[4]氮杂ac作为新的荧光离子载体：通过荧光变化的“分子跆拳道”过程。

  摘要：

  合成了一系列新的基于杯芳烃的氟离子载体。使用我们的新杯芳烃衍生物，其中冠状醚和氮杂冠状醚作为两个结合位点，发现金属离子在这两个配体之间选择性地选择了更好的结合口袋。Ag（+）-K（+），Cu（2 +）-K（+）和Ag（+）-Cs（+）对之间有趣的“分子跆拳道”过程很容易通过荧光变化进行监测。

  DOI：

  10.1021/jo010877w
• 作为产物：
  描述：

  9-(4-Methylphenyl)sulfonyl-40,41-dipropoxy-3,6,12,15-tetraoxa-9-azahexacyclo[15.15.7.123,27.134,38.02,29.016,21]hentetraconta-1(32),2(29),16(21),17,19,23,25,27(41),30,34(40),35,37-dodecaene 在 sodium amalgam 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.0h， 以52%的产率得到25,27-bis(1-propyloxy)calix[4]arene azacrown-5
  参考文献：
  名称：

  Synthesis and Metal Ion Complexation Studies of Proton-Ionizable Calix[4]azacrown Ethers in the 1,3-Alternate Conformation

  摘要：

  A series of novel N-chromogenic calix[4]arene azacrown ethers were synthesized as selective extractants of potassium ion. 1,3-Alternate calix[4]arene azacrown ethers were prepared by reacting 25,27-dipropyloxy-26,28-bis(5-chloro-3-oxapentyloxy) calix[4]arenes with p-toluenesulfonamide in the presence of potassium carbonate. The coupling reaction of calix[4]arene azacrown ether with 2-hydroxy-5-nitrobenzyl bromide in the presence of triethylamine in THF gave the chromogenic calix[4]arene azacrown ether in moderate yield. These compounds show high potassium selectivity, over other metal ions as shown by two-phase extraction, bulk liquid membrane, and H-1 NMR studies on a ligand-metal complex. It is assumed that the OH of the chromogenic group attached on nitrogen can assist the complexation by encapsulation of the metal.

  DOI：

  10.1021/jo9912754

文献信息

• Chromogenic Indoaniline Armed-Calix[4]azacrowns
  作者：Jong Seung Kim、Ok Jae Shon、Seung Hwan Yang、Jong Yeol Kim、Moon Jib Kim

  DOI：10.1021/jo0201169

  日期：2002.9.1

  Two novel chromogenic 1,3-alternate calix[4]azacrown (1) and calix[4]-bis-azacrown (2) in which an indoaniline chromophore was attached on the nitrogen atom of the azacrown unit with one methylene spacer were synthesized. The H-1 NMR spectrum of the ligand 1 and Ca2+ proved that the metal ion is entrapped by the calix[4]azacrown unit and by the conjugated indoaniline system. From the UV/vis band shifts upon metal ion complexation, Zn2+ ion was found to give the largest band shifts compared to other metal cations, indicating that Zn2+ ion (K-a = 18 760 M-1 for 1 and K-a = 19 930 M-1 for 2) was selectively encapsulated by the calix[4]azacrown cavity with assistance of the pendent indoaniline sidearm.
• Kim, Jong Seung; Shon, Ok Jae; Sim, Wonbo, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 1, p. 31 - 36
  作者：Kim, Jong Seung、Shon, Ok Jae、Sim, Wonbo、Kim, Sun Kyu、Cho, Moon Hwan、Kim, Jin-Gyu、Suh, Il-Hwan、Kim, Dong Won

  DOI：——

  日期：——
• Synthesis and Metal Ion Complexation Studies of Proton-Ionizable Calix[4]azacrown Ethers in the 1,3-Alternate Conformation
  作者：Jong Seung Kim、Ok Jae Shon、Jong Won Ko、Moon Hwan Cho、Ill Yong Yu、Jacques Vicens

  DOI：10.1021/jo9912754

  日期：2000.4.1

  A series of novel N-chromogenic calix[4]arene azacrown ethers were synthesized as selective extractants of potassium ion. 1,3-Alternate calix[4]arene azacrown ethers were prepared by reacting 25,27-dipropyloxy-26,28-bis(5-chloro-3-oxapentyloxy) calix[4]arenes with p-toluenesulfonamide in the presence of potassium carbonate. The coupling reaction of calix[4]arene azacrown ether with 2-hydroxy-5-nitrobenzyl bromide in the presence of triethylamine in THF gave the chromogenic calix[4]arene azacrown ether in moderate yield. These compounds show high potassium selectivity, over other metal ions as shown by two-phase extraction, bulk liquid membrane, and H-1 NMR studies on a ligand-metal complex. It is assumed that the OH of the chromogenic group attached on nitrogen can assist the complexation by encapsulation of the metal.
• Pyrene-Armed Calix[4]azacrowns as New Fluorescent Ionophores:  “Molecular Taekowndo” Process via Fluorescence Change
  作者：Jong Seung Kim、Ok Jae Shon、Jeong Ah Rim、Sook Kyung Kim、Juyoung Yoon

  DOI：10.1021/jo010877w

  日期：2002.4.1

  A series of new calixarene-based fluoroionophores were synthesized. With our new calixarene derivative bearing a crown ether and an azacrown ether as two binding sites, the metal ion was found to selectively choose its better binding pocket between these two ligands. Interesting "molecular taekowndo" processes between Ag(+)-K(+), Cu(2+)-K(+), and Ag(+)-Cs(+) pairs were easily monitored via fluorescence

  合成了一系列新的基于杯芳烃的氟离子载体。使用我们的新杯芳烃衍生物，其中冠状醚和氮杂冠状醚作为两个结合位点，发现金属离子在这两个配体之间选择性地选择了更好的结合口袋。Ag（+）-K（+），Cu（2 +）-K（+）和Ag（+）-Cs（+）对之间有趣的“分子跆拳道”过程很容易通过荧光变化进行监测。