5,17-dicyano-11,23-diiodo-25,26,27,28-tetrapropoxycalix[4]arene | 198989-77-4

• 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-11,23-diiodo-25,26,27,28-tetrapropoxycalix[4]arene
• 英文别名: 11,23-Diiodo-25,26,27,28-tetrapropoxypentacyclo[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-5,17-dicarbonitrile
• CAS: 198989-77-4
• 化学式: C₄₂H₄₄I₂N₂O₄
• 分子量: 894.631
• InChiKey: GXHYJUFDIAMFRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  50
• 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-11,23-diiodo-25,26,27,28-tetrapropoxycalix[4]arene 在 4-二甲氨基吡啶 、 三氟化硼四氢呋喃络合物 作用下， 以 二氯甲烷 为溶剂， 生成 N-[[17-[(adamantane-1-carbonylamino)methyl]-11,23-diiodo-25,26,27,28-tetrapropoxy-5-pentacyclo[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-dodecaenyl]methyl]adamantane-1-carboxamide
  参考文献：
  名称：

  Calix[4]arene-Based Receptors with Hydrogen-Bonding Groups Immersed into a Large Cavity

  摘要：

  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.

  DOI：

  10.1021/jo9804543
• 作为产物：
  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