25-(3-amino)propoxy-26,27,28-tripropoxycalix[4]arene | 1304030-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25-(3-amino)propoxy-26,27,28-tripropoxycalix[4]arene
• 英文别名: 3-[(26,27,28-Tripropoxy-25-pentacyclo[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-dodecaenyl)oxy]propan-1-amine
• CAS: 1304030-57-6
• 化学式: C₄₀H₄₉NO₄
• 分子量: 607.833
• InChiKey: HBSVZDMZDUIWET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对羧基苯磺酰胺 、 25-(3-amino)propoxy-26,27,28-tripropoxycalix[4]arene 在 N,N-二异丙基乙胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.34h， 以41%的产率得到25-(4-sulfamoylbenzenamido)propoxy-26,27,28-tripropoxycalix[4]arene
  参考文献：
  名称：

  包含磺酰胺部分的杯芳烃：用于碳酸酐酶抑制的多功能配体

  摘要：

  带有以初级苯磺酰胺终止的臂的杯芳烃衍生物证明了它们抑制人碳酸酐酶的能力，并且在酶的不同异构体中具有显着的效率和选择性。X射线衍射数据和MD计算支持苯磺酰胺臂渗透到酶活性位点的漏斗中并与蛋白质Zn 2+离子相互作用的结合模式。

  DOI：

  10.1002/chem.202103527
• 作为产物：
  描述：

  tri(n-propoxy)calix[4]arene 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 25-(3-amino)propoxy-26,27,28-tripropoxycalix[4]arene
  参考文献：
  名称：

  CO₂ Capture by Multivalent Amino-Functionalized Calix[4]arenes: Self-Assembly, Absorption, and QCM Detection Studies

  摘要：

  The reactivity of CO2 with polyamino substrates based on calix[4]arenes and on a difunctional, noncyclic model has been studied. All the compounds react with CO2 in chloroform to form ammonium carb innate salts. However, the number, topology, and conformational features of the amino-functionalized arms present on the multivalent scaffold have a remarkable influence on the reaction efficiency and on the product composition. Tetraaminocalix[4]arenes 1-3 rapidly and efficiently react with 2 equiv of CO2, yielding highly stable hydrogen-bonded dimers formed by the self-assembly of two bis-ammonium bis-carbamate intramolecular salts. 1,3-Diaminocalix[4]arene 4 absorbs 1 mol of CO2, affording less stable zwitterionic ammonium carbamates. Gemini compound 5 reacts with CO2 in a 1:1 stoichiometry, forming hydrogen. bonded dimers of ammonium carbamate derivatives of moderate stability. For upper rim 1,3-diaminocalix[4]arene 6, in addition to the labile intramolecular salt, the presence of a self-assembled polymer was also detected. These systems were fully characterized in solution by H-1 and C-13 NMR spectroscopy, whereas the corresponding gas-solid reactions were further investigated by QCM measurements. Interestingly, the high affinity and reversibility of CO2 uptake shown by 1,3-diamino calix[4]arene 4 enabled us to attain a promising QCM device for carbon dioxide sensing.

  DOI：

  10.1021/jo200650f

文献信息

• Calixarenes Incorporating Sulfonamide Moieties: Versatile Ligands for Carbonic Anhydrases Inhibition
  作者：Davide Sbravati、Alessandro Bonardi、Silvia Bua、Andrea Angeli、Marta Ferraroni、Alessio Nocentini、Alessandro Casnati、Paola Gratteri、Francesco Sansone、Claudiu T. Supuran

  DOI：10.1002/chem.202103527

  日期：2022.1.27

  with primary benzensulfonamides demonstrated their ability of inhibiting human Carbonic Anhydrases with significant efficiency and selectivity among different isoforms of the enzymes. A mode of binding where the benzensulfonamide arm penetrates into the funnel of the enzyme active site and interacts with the protein Zn2+ ion is supported by X-ray diffraction data and MD calculations.

  带有以初级苯磺酰胺终止的臂的杯芳烃衍生物证明了它们抑制人碳酸酐酶的能力，并且在酶的不同异构体中具有显着的效率和选择性。X射线衍射数据和MD计算支持苯磺酰胺臂渗透到酶活性位点的漏斗中并与蛋白质Zn 2+离子相互作用的结合模式。
• CO₂ Capture by Multivalent Amino-Functionalized Calix[4]arenes: Self-Assembly, Absorption, and QCM Detection Studies
  作者：Laura Baldini、Monica Melegari、Valentina Bagnacani、Alessandro Casnati、Enrico Dalcanale、Francesco Sansone、Rocco Ungaro

  DOI：10.1021/jo200650f

  日期：2011.5.20

  The reactivity of CO2 with polyamino substrates based on calix[4]arenes and on a difunctional, noncyclic model has been studied. All the compounds react with CO2 in chloroform to form ammonium carb innate salts. However, the number, topology, and conformational features of the amino-functionalized arms present on the multivalent scaffold have a remarkable influence on the reaction efficiency and on the product composition. Tetraaminocalix[4]arenes 1-3 rapidly and efficiently react with 2 equiv of CO2, yielding highly stable hydrogen-bonded dimers formed by the self-assembly of two bis-ammonium bis-carbamate intramolecular salts. 1,3-Diaminocalix[4]arene 4 absorbs 1 mol of CO2, affording less stable zwitterionic ammonium carbamates. Gemini compound 5 reacts with CO2 in a 1:1 stoichiometry, forming hydrogen. bonded dimers of ammonium carbamate derivatives of moderate stability. For upper rim 1,3-diaminocalix[4]arene 6, in addition to the labile intramolecular salt, the presence of a self-assembled polymer was also detected. These systems were fully characterized in solution by H-1 and C-13 NMR spectroscopy, whereas the corresponding gas-solid reactions were further investigated by QCM measurements. Interestingly, the high affinity and reversibility of CO2 uptake shown by 1,3-diamino calix[4]arene 4 enabled us to attain a promising QCM device for carbon dioxide sensing.