2-(5-azidopentyl)-25,26,27,28-tetramethoxy-p-tert-butylcalix[4]arene | 1333321-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-azidopentyl)-25,26,27,28-tetramethoxy-p-tert-butylcalix[4]arene
• 英文别名: 2-(5-Azidopentyl)-5,11,17,23-tetratert-butyl-25,26,27,28-tetramethoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene；2-(5-azidopentyl)-5,11,17,23-tetratert-butyl-25,26,27,28-tetramethoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 1333321-66-6
• 化学式: C₅₃H₇₃N₃O₄
• 分子量: 816.18
• InChiKey: WXYXENFNMPWQCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  60
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-azidopentyl)-25,26,27,28-tetramethoxy-p-tert-butylcalix[4]arene 、 1-己炔 在 铜 、 copper(II) sulfate 作用下， 以 水 、 叔丁醇 为溶剂， 以41.8%的产率得到2-(5-((4-butyl)-1H-1,2,3-triazolyl)pentyl)-25,26,27,28-tetramethoxy-p-tert-butylcalix[4]arene
  参考文献：
  名称：

  Synthesis and ‘click’ cycloaddition reactions of tetramethoxy- and tetrapropoxy-2-(ω-azidoalkyl)calix[4]arenes

  摘要：

  2-(omega-Chloroalkyl)tetramethoxycalix[4]arenes are converted to 2-(omega-azidoalkyl)tetramethoxy- and cone-2-(omega-azidoalkyl)tetrapropoxycalix[4]arenes, the former by substitution and the latter by demethylation to 2-(omega-chloroalkyl)tetrahydroxycalix[4]arenes, which are O-propylated before substitution of azide for chloride. The azide-terminated calixarenes undergo Cu(I)-catalyzed 1,3-cycloaddition to terminal alkynes to give 1,4-disubstituted 1,2,3-triazoles, demonstrating the potential to couple calixarenes from a tether at the 2-position (methylene bridge) to substrates that bear a terminal alkyne group. The cone conformation of cone-2-(4-chlorobutyl)tetrapropoxycalix[4]arene has been confirmed by X-ray diffraction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.022
• 作为产物：
  描述：

  2-(5-chloropentyl)tetramethoxy-p-tert-butylcalix[4]arene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(5-azidopentyl)-25,26,27,28-tetramethoxy-p-tert-butylcalix[4]arene
  参考文献：
  名称：

  Bis-calix[4]arene-based podants using the bridge position as a constructive mode of subunit connection

  摘要：

  本文介绍了通过不同长度的柔性亚烷基链或更刚性的双环三唑修饰连接元件将两个钙钛矿进行桥式连接的合成途径。核磁共振测量和 MM 计算表明，相当柔性的共轭物适合与适当大小的中性和阴离子客体形成包合物。

  DOI：

  10.1007/s10847-013-0338-6

文献信息

• Synthesis and ‘click’ cycloaddition reactions of tetramethoxy- and tetrapropoxy-2-(ω-azidoalkyl)calix[4]arenes
  作者：Michael J. Hardman、Ashley M. Thomas、Louise T. Carroll、Linus C. Williams、Sean Parkin、Jordan L. Fantini

  DOI：10.1016/j.tet.2011.07.022

  日期：2011.9

  2-(omega-Chloroalkyl)tetramethoxycalix[4]arenes are converted to 2-(omega-azidoalkyl)tetramethoxy- and cone-2-(omega-azidoalkyl)tetrapropoxycalix[4]arenes, the former by substitution and the latter by demethylation to 2-(omega-chloroalkyl)tetrahydroxycalix[4]arenes, which are O-propylated before substitution of azide for chloride. The azide-terminated calixarenes undergo Cu(I)-catalyzed 1,3-cycloaddition to terminal alkynes to give 1,4-disubstituted 1,2,3-triazoles, demonstrating the potential to couple calixarenes from a tether at the 2-position (methylene bridge) to substrates that bear a terminal alkyne group. The cone conformation of cone-2-(4-chlorobutyl)tetrapropoxycalix[4]arene has been confirmed by X-ray diffraction. (C) 2011 Elsevier Ltd. All rights reserved.
• Bis-calix[4]arene-based podants using the bridge position as a constructive mode of subunit connection
  作者：Conrad Fischer、Edwin Weber

  DOI：10.1007/s10847-013-0338-6

  日期：2014.6

  Synthetic pathways for a bridge type connection of two calixarenes by a flexible alkylene chain or a more rigid bistriazole modified connection element of different length are presented. NMR measurements as well as MM calculations point to rather flexible conjugates showing suitable requirements for a potential formation of inclusion complexes with neutral and anionic guests of appropriate size.

  本文介绍了通过不同长度的柔性亚烷基链或更刚性的双环三唑修饰连接元件将两个钙钛矿进行桥式连接的合成途径。核磁共振测量和 MM 计算表明，相当柔性的共轭物适合与适当大小的中性和阴离子客体形成包合物。