5,11,17,23-tetra-tert-butyl-25,27-bis(isocyanatopropoxy)-26,28-dihydroxycalix[4]arene | 936716-64-2

• 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-25,27-bis(isocyanatopropoxy)-26,28-dihydroxycalix[4]arene
• 英文别名: 5,11,17,23-Tetratert-butyl-26,28-bis(3-isocyanatopropoxy)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-dodecaene-25,27-diol
• CAS: 936716-64-2
• 化学式: C₅₂H₆₆N₂O₆
• 分子量: 815.106
• InChiKey: KRCBRXAHFQEVQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  60
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-bis(isocyanatopropoxy)-26,28-dihydroxycalix[4]arene 、 甘氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以70%的产率得到Methyl 2-[3-[[5,11,17,23-tetratert-butyl-26,28-dihydroxy-27-[3-[(2-methoxy-2-oxoethyl)carbamoylamino]propoxy]-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]propylcarbamoylamino]acetate
  参考文献：
  名称：

  N-Linked Peptidocalix[4]arene Bisureas as Enantioselective Receptors for Amino Acid Derivatives

  摘要：

  Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius rearrangement from the corresponding carboxylic acid derivatives. The conformational properties of the ligands 1 and 2 were investigated by means of a combined NMR and molecular modeling study which evidences that they are deeply influenced by strong intramolecular H-bonds between the urea NH groups and the vicinal phenolic oxygen atoms or the opposite urea CO group. Complexation studies performed by ESI-MS and NMR spectroscopy in acetone solution show that the binding ability of these bisurea hosts decreases by increasing the side chain size of the amino acid. Host 2b has a remarkable binding ability for the N-acetyl-D-phenylalaninate anion with an interesting enantioselectivity (K-ass(D)/K-ass(L) = 4.14), which is explained on the basis of a three-point interaction mode of binding.

  DOI：

  10.1021/jo062410x
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 氢氧化钾 、 草酰氯 、 叠氮基三甲基硅烷 、 四丁基碘化铵 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 40.0h， 生成 5,11,17,23-tetra-tert-butyl-25,27-bis(isocyanatopropoxy)-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  N-Linked Peptidocalix[4]arene Bisureas as Enantioselective Receptors for Amino Acid Derivatives

  摘要：

  Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius rearrangement from the corresponding carboxylic acid derivatives. The conformational properties of the ligands 1 and 2 were investigated by means of a combined NMR and molecular modeling study which evidences that they are deeply influenced by strong intramolecular H-bonds between the urea NH groups and the vicinal phenolic oxygen atoms or the opposite urea CO group. Complexation studies performed by ESI-MS and NMR spectroscopy in acetone solution show that the binding ability of these bisurea hosts decreases by increasing the side chain size of the amino acid. Host 2b has a remarkable binding ability for the N-acetyl-D-phenylalaninate anion with an interesting enantioselectivity (K-ass(D)/K-ass(L) = 4.14), which is explained on the basis of a three-point interaction mode of binding.

  DOI：

  10.1021/jo062410x