5,11,17,23-tetrakis(t-butyl)-25-allyloxy-26,27,28-tris-(n-propyloxy)calix[4]arene | 816437-79-3

• 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-tetrakis(t-butyl)-25-allyloxy-26,27,28-tris-(n-propyloxy)calix[4]arene
• 英文别名: 25-allyloxy-5,11,17,23-tetra-tert-butyl-26,27,28-tripropoxycalix<4>arene；5,11,17,23-Tetratert-butyl-25-prop-2-enoxy-26,27,28-tripropoxypentacyclo[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
• CAS: 816437-79-3
• 化学式: C₅₆H₇₈O₄
• 分子量: 815.233
• InChiKey: RBKKMRNTTSWZNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.6
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(t-butyl)-25-allyloxy-26,27,28-tris-(n-propyloxy)calix[4]arene 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.5h， 以95%的产率得到5,11,17,23-tetrakis(t-butyl)-25-(3'-hydroxypropyloxy)-26,27,28-tris-(n-propyloxy)calix[4]arene
  参考文献：
  名称：

  Polymer-supported calix[4]arenes for sensing and conversion of NO2/N2O4

  摘要：

  The use of simple calix[4]arenes 1a,b for NO2/N2O4 sensing and conversion is demonstrated, both in solution and in the solid state. Upon reacting with these gases, compounds la,b encapsulate reactive NO+ cations within their cavities with the formation of deeply colored (gimel(max) similar to 570 nm) charge-transfer complexes 2a,b. Further functionalization of the calix[4]arene platform is reported for attachment to solid supports. Polymer-supported calixarene material 3 was prepared, which reversibly traps NO2/N2O4 with the formation of nitrosonium storing polymer 4. Material 4 was effectively used for nitrosation of amides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.063
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 potassium carbonate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 84.0h， 生成 5,11,17,23-tetrakis(t-butyl)-25-allyloxy-26,27,28-tris-(n-propyloxy)calix[4]arene
  参考文献：
  名称：

  Polymer-supported calix[4]arenes for sensing and conversion of NO2/N2O4

  摘要：

  The use of simple calix[4]arenes 1a,b for NO2/N2O4 sensing and conversion is demonstrated, both in solution and in the solid state. Upon reacting with these gases, compounds la,b encapsulate reactive NO+ cations within their cavities with the formation of deeply colored (gimel(max) similar to 570 nm) charge-transfer complexes 2a,b. Further functionalization of the calix[4]arene platform is reported for attachment to solid supports. Polymer-supported calixarene material 3 was prepared, which reversibly traps NO2/N2O4 with the formation of nitrosonium storing polymer 4. Material 4 was effectively used for nitrosation of amides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.063

文献信息

• Towards Supramolecular Fixation of NOX Gases: Encapsulated Reagents for Nitrosation
  作者：Yanlong Kang、Grigory V. Zyryanov、Dmitry M. Rudkevich

  DOI：10.1002/chem.200400939

  日期：2005.3.4

  nitrosated with much lower yields (<8 %). Enantiomerically pure encapsulating reagent 2 d was tested for nitrosation of racemic amide 5 t, showing modest but reproducible stereoselectivity and approximately 15 % ee. Given high affinity to NO+ species, which can be generated by a number of NOX gases, these supramolecular reagents and materials may be useful for NOX entrapment and separation in the environment

  已证明在溶液和固态下使用简单的杯[4]芳烃进行化学转化为NO2 / N2O4气体。与这些气体反应后，杯芳烃1在其腔内封入亚硝基（NO +）阳离子，并形成稳定的杯芳烃-NO +络合物2。空穴效应控制着它们的反应性和选择性。配合物2被有效地用于仲酰胺5的亚硝化，包括手性衍生物。观察到独特的尺寸-形状选择性，允许较少拥挤的5-ae N-Me酰胺进行独家亚硝化（产率高达95％）。由于对包封的NO +试剂的阻碍方法，大块的N-Alk（Alk> Me）基材5不反应。制备了坚固的硅胶基杯芳烃材料3，其可逆地捕集到 / ，并形成储存有NO +的硅胶4。对于材料4，对于亚硝化，观察到相似的尺寸-形状选择性。获得N-Me-N-亚硝基衍生物6 d，e的收率约为30％，而将体积较大的酰胺亚硝化的收率要低得多（<8％）。测试了对映体纯的包封试剂2d的消旋酰胺5t的亚硝化，显示适度但可重现的立体选择性和
• Synthesis and metal-binding properties of oligo-calixarenes. an approach towards the calix[4]arene-based dendrimers
  作者：Pavel Lhotak、Seiji Shinkai

  DOI：10.1016/0040-4020(95)00408-z

  日期：1995.7

  A series of bis-calix[4]arene derivatives 4a-h (cone conformation) linked through the phenolic oxygens with the help of a single aliphatic chain (lower rim-lower rim connection) was obtained in high yields (50-80%) by alkylation of 25, 26, 27-tripropoxy-28-hydroxycalix [4]arenes 2a, 2b with 0.5 equiv. of Br-(CH2)(n)-Br in the presence of NaH. The same reaction with excess dibromides yielded corresponding bromoalkyl derivatives 3a-c which were used for construction of oligo-calix[4]arenes (bis, tris, pentakis) - a new family of calix[4]arene derivatives representing the first step on the way towards the calixarene-based dendrimers. The metal complexation behavior of newly prepared compounds was investigated with the help of H-1 NMR spectroscopy.