5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(N-ethyl-carbamoylmethoxy)calix[4]arene | 306272-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(N-ethyl-carbamoylmethoxy)calix[4]arene
• 英文别名: N-ethyl-2-[[5,11,17,23-tetratert-butyl-26,27,28-tris[2-(ethylamino)-2-oxoethoxy]-25-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]oxy]acetamide
• CAS: 306272-43-5
• 化学式: C₆₀H₈₄N₄O₈
• 分子量: 989.349
• InChiKey: YMJJNNAUFSEBKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  72
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(N-ethyl-carbamoylmethoxy)calix[4]arene 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以72%的产率得到25,26,27,28-tetrakis(N-ethylthiocarbamoylmethoxy)-5,11,17,23-tetratert-butylcalix[4]arene
  参考文献：
  名称：

  Lower rim substituted p-tert-butyl calix[4]arene; Part 14. Synthesis, structures and binding studies of calix[4]arene thioamides

  摘要：

  我们合成了一些对叔丁基钙[4]炔硫代酰胺，并通过 1H-NMR 和元素分析对其进行了表征。化合物 1-5 是具有-CH2-C(=S)-N-X 基团的 O 取代衍生物，其中 NX = morpholidyl, NEt2, NHC2H4Ph, NHCH2Ph 和 NHEt 分别为-CH2-C(=S)-N-X 基团。本文展示了配体 1、3、5 和复合物 3-Pb(ClO4)2（化合物 6）的 X 射线结构，并确定了它们略微扭曲的锥形构象。研究了硫酰胺功能的性质（二级或三级）对一些选定金属阳离子萃取性的影响。所有这些钙烯类化合物对 Ag+ 的萃取率都最高，而三级硫代酰胺对 Pb2+ 的萃取率则高于二级硫代酰胺。

  DOI：

  10.1007/s10847-010-9735-2

文献信息

• UV-Vis and ESI MS/MS Study of Calix[4]arene Derivatives and Their Lanthanide Complexes
  作者：Marina Tranfić Bakić、Mariela Soledad Espinosa、Nikola Cindro、Leo Frkanec、Paola Alejandra Babay、Nives Galić

  DOI：10.5562/cca3288

  日期：——

  Coordination properties of calix[4]arenes bearing substituents on the lower rim: tetraethyl ester (1), tetraethylamide (2), and newly synthesized tetraethylmethylamide derivative (3), towards selected lanthanide cations (La3+, Eu3+, Yb3+) were studied by spectrophotometric titrations. No complexation was observed with ester derivative, while amide derivatives formed 1:1 complexes and bound lanthanide cations very efficiently (lgK(La2) = 5.1; lgK(Eu2) >= 6; lgK(Yb2) >= 6; lgK(La3) >= 6; lgK(Eu3) >= 6; lgK(Yb3) >= 6). The ligands and complexes were also analysed by ESI MS and MS/MS spectrometry. Both inductive cleavage and proton rearrangement fragmentation reactions were observed. Corresponding fragmentation pathways were proposed. The results obtained by MS analysis were in accordance with those obtained by spectrophotometric titrations.
• Lower rim substituted p-tert-butyl calix[4]arene; Part 14. Synthesis, structures and binding studies of calix[4]arene thioamides
  作者：Maria Bocheńska、Joanna Kulesza、Jarosław Chojnacki、Françoise Arnaud-Neu、Véronique Hubscher-Bruder

  DOI：10.1007/s10847-010-9735-2

  日期：2010.10

  A number of p-tert-butylcalix[4]arene thioamides were synthesized and characterized by 1H-NMR and elemental analysis. Compounds 1–5 are O-substituted derivatives with –CH2–C(=S)–N–X groups, where NX = morpholidyl, NEt2, NHC2H4Ph, NHCH2Ph and NHEt, respectively. The X-ray structures of the ligands 1, 3, 5 and of the complex 3·Pb(ClO4)2, (compound 6), are presented and their slightly distorted cone conformation is established. The influence of the nature of the thioamide functions (secondary or tertiary) on the extractability of some selected metal cations was investigated. Whereas all these calixarenes show the highest extraction level for Ag+, tertiary thioamides are more efficient extractants for Pb2+ than secondary thioamides.

  我们合成了一些对叔丁基钙[4]炔硫代酰胺，并通过 1H-NMR 和元素分析对其进行了表征。化合物 1-5 是具有-CH2-C(=S)-N-X 基团的 O 取代衍生物，其中 NX = morpholidyl, NEt2, NHC2H4Ph, NHCH2Ph 和 NHEt 分别为-CH2-C(=S)-N-X 基团。本文展示了配体 1、3、5 和复合物 3-Pb(ClO4)2（化合物 6）的 X 射线结构，并确定了它们略微扭曲的锥形构象。研究了硫酰胺功能的性质（二级或三级）对一些选定金属阳离子萃取性的影响。所有这些钙烯类化合物对 Ag+ 的萃取率都最高，而三级硫代酰胺对 Pb2+ 的萃取率则高于二级硫代酰胺。