7,13,19,25-tetra-tert-butyl-27,29-bis[[(N0-tert-butylureido)butyl]oxy]-28,30-dibenzyloxy-2,3-dihomo-3-oxacalix[4]arene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7,13,19,25-tetra-tert-butyl-27,29-bis[[(N0-tert-butylureido)butyl]oxy]-28,30-dibenzyloxy-2,3-dihomo-3-oxacalix[4]arene
• 英文别名: 1-Tert-butyl-3-[4-[[5,11,17,25-tetratert-butyl-27-[4-(tert-butylcarbamoylamino)butoxy]-28,30-bis(phenylmethoxy)-21-oxapentacyclo[21.3.1.13,7.19,13.115,19]triaconta-1(27),3,5,7(30),9(29),10,12,15(28),16,18,23,25-dodecaen-29-yl]oxy]butyl]urea；1-tert-butyl-3-[4-[[5,11,17,25-tetratert-butyl-27-[4-(tert-butylcarbamoylamino)butoxy]-28,30-bis(phenylmethoxy)-21-oxapentacyclo[21.3.1.13,7.19,13.115,19]triaconta-1(27),3,5,7(30),9(29),10,12,15(28),16,18,23,25-dodecaen-29-yl]oxy]butyl]urea
• 化学式: C₇₇H₁₀₆N₄O₇
• 分子量: 1199.71
• InChiKey: SWBHOKXNIURQPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.2
• 重原子数：
  88
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-叔丁基二高氧杯[4]芳烃 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 41.0h， 生成 7,13,19,25-tetra-tert-butyl-27,29-bis[[(N0-tert-butylureido)butyl]oxy]-28,30-dibenzyloxy-2,3-dihomo-3-oxacalix[4]arene
  参考文献：
  名称：

  Synthesis and anion binding properties of new dihomooxacalix[4]arene diurea and dithiourea receptors

  摘要：

  Functionalization of the lower rim of p-tert-butyldihomooxacalix[4]arene with two (thio)ureido moieties provided new diurea (n-propyl 5a, tert-butyl 5b and phenyl 5c) and dithiourea (phenyl 5d) derivatives, all in the cone conformation, as shown by NMR studies. The X-ray crystal structure of 5c is reported. The binding ability of these neutral receptors towards a large variety of anions was assessed by H-1 NMR titrations. The structures and complexation energies of some complexes were also studied using DFT methods. The data showed that, in general, the association constants decrease with decrease of anion basicity and they are strongly dependent on the nature of the substituent at the urea moiety. Phenyl(thio)urea derivatives 5c and 5d are the best anion receptors, showing the strongest complexation for F-(log K-ass=2.70 and 2.75, respectively) and also for the oxoanions AcO-, BzO(-) and H2PO4-. These results were corroborated by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.020

文献信息

• Synthesis and anion binding properties of new dihomooxacalix[4]arene diurea and dithiourea receptors
  作者：Paula M. Marcos、Filipa A. Teixeira、Manuel A.P. Segurado、José R. Ascenso、Raul J. Bernardino、Giovanna Brancatelli、Silvano Geremia

  DOI：10.1016/j.tet.2014.07.020

  日期：2014.9

  Functionalization of the lower rim of p-tert-butyldihomooxacalix[4]arene with two (thio)ureido moieties provided new diurea (n-propyl 5a, tert-butyl 5b and phenyl 5c) and dithiourea (phenyl 5d) derivatives, all in the cone conformation, as shown by NMR studies. The X-ray crystal structure of 5c is reported. The binding ability of these neutral receptors towards a large variety of anions was assessed by H-1 NMR titrations. The structures and complexation energies of some complexes were also studied using DFT methods. The data showed that, in general, the association constants decrease with decrease of anion basicity and they are strongly dependent on the nature of the substituent at the urea moiety. Phenyl(thio)urea derivatives 5c and 5d are the best anion receptors, showing the strongest complexation for F-(log K-ass=2.70 and 2.75, respectively) and also for the oxoanions AcO-, BzO(-) and H2PO4-. These results were corroborated by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.