5,17-dicyano-25,26,27,28-tetrakis(1-propyloxy)calix[4]arene | 950744-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,17-dicyano-25,26,27,28-tetrakis(1-propyloxy)calix[4]arene
• 英文别名: 5,17-bis-cyano-25,26,27,28-tetrapropyloxy-calix[4]arene；25,26,27,28-Tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5,17-dicarbonitrile
• CAS: 950744-67-9
• 化学式: C₄₂H₄₆N₂O₄
• 分子量: 642.838
• InChiKey: JUGAWPXJQKEXQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,17-dicyano-25,26,27,28-tetrakis(1-propyloxy)calix[4]arene 在 碘 、 silver trifluoroacetate 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以81%的产率得到5,17-dicyano-11,23-diiodo-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  Synthesis of Upper and Lower Rim Binaphthyl Bridged Calix[4]arenes:  New Potential Chiral Hosts for Molecular Recognition and Catalysis

  摘要：

  New chiral upper and lower rim (R)-binaphthyl-bridged calix[4]arenes in the cone conformation (5, 10, 11, 15, 17, 18) have been synthesized by exploiting the selective functionalization of the calix[4]arene skeleton, The conformational properties of the new hosts in CDCl3 and DMSO-d(6) have been clarified by dynamic NMR measurements, and their complexation properties toward neutral molecules, alkali metal, and silver(I) cations have been explored. The upper rim binaphthyl-bridged calix[4]arene 5 is able to form a 1:1 complex with Ag+ in CDCl3:CD3OD 1:1 v/v solution, where the silver cation is encapsulated into the apolar cavity. The determined association constant (log K = 3.51) is substantially higher than for unbridged calix[4]arenes in the cone conformation. These new macrobicyclic compounds are potential hosts for chiral recognition and catalysis.

  DOI：

  10.1021/jo9706990
• 作为产物：
  描述：

  11,23-dibromo-26,28-dipropoxycalix[4]arene-25,27-diol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 5,17-dicyano-25,26,27,28-tetrakis(1-propyloxy)calix[4]arene
  参考文献：
  名称：

  Casnati, Alessandro; Fochi, Mariacristina; Minari, Patrizia, Gazzetta chimica Italiana, 1996, vol. 126, # 2, p. 99 - 106

  摘要：

  DOI：

文献信息

• Cyanocalix[4]arenes: synthesis, crystal structures and reactivity studies
  作者：Malcolm J. Applewhite、Delia A. Haynes、Gareth E. Arnott

  DOI：10.1080/10610278.2015.1121268

  日期：2016.6.2

  Herein, we describe an improved method to synthesise mono-, di- and tetra-cyanocalix[4]arene and report their crystal structure determinations. We also report our attempts to further functionalise the cyanocalix[4]arenes into dithiadiazolyl-calix[4]arenes, and propose a hypothesis as to why the cyano group on a calix[4]arene is an extremely challenging group to modify.

  摘要 在此，我们描述了一种合成单、二和四氰基杯[4]芳烃的改进方法，并报告了它们的晶体结构测定。我们还报告了我们将氰基杯[4]芳烃进一步官能化为二噻二唑基-杯[4]芳烃的尝试，并提出了一个假设，即为什么杯[4]芳烃上的氰基是一个极具挑战性的修饰基团。
• Vreekamp, Remko H.; Verboom, Willem; Reinhoudt, David N., Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 7-8, p. 363 - 370
  作者：Vreekamp, Remko H.、Verboom, Willem、Reinhoudt, David N.

  DOI：——

  日期：——
• Calix[4]arene-Based Receptors with Hydrogen-Bonding Groups Immersed into a Large Cavity
  作者：Evgueni Pinkhassik、Vladimir Sidorov、Ivan Stibor

  DOI：10.1021/jo9804543

  日期：1998.12.1

  A one-pot procedure, which combines the Ritter and Friedel-Crafts reactions, produced the first members of a new type of calix[4]arene-based receptors. The cavity in these receptors is formed by a calix[4]arene framework fixed in the cone conformation and bulky adamantyl or (and) phenylacetylene moieties. Amido and amino groups were used as potential hygrogen bond donors. Preliminary studies revealed interesting complexation properties, in particular, the tetrahedral recognition of water molecules performed by one of the receptors.