11,23-Di-tert-butyl-26,28-dihydroxy-5,17-dinitro-25,27-dipentyloxycalix[4]arene | 181711-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11,23-Di-tert-butyl-26,28-dihydroxy-5,17-dinitro-25,27-dipentyloxycalix[4]arene
• 英文别名: 5,17-Ditert-butyl-11,23-dinitro-26,28-dipentoxypentacyclo[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: 181711-23-9
• 化学式: C₄₆H₅₈N₂O₈
• 分子量: 766.975
• InChiKey: ZLHOHHCILZTTOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  56
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11,23-Di-tert-butyl-26,28-dihydroxy-5,17-dinitro-25,27-dipentyloxycalix[4]arene 在 Ra-Ni 氢气 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Selective Derivatization of Calix[4]arenes via Amino Groups Attached to the Wide Rim

  摘要：

  提出了一种新的合成策略，用于在宽口环上的特定位置引入硝基和邻酰苯胺基的卡立克斯[4]芳烃四醚衍生物。由于这两种基团都是氨基功能的前体，因此经不同的N-酰基氨基取代的卡立克斯[4]芳烃四醚很容易在四个步骤内获得。合成前体的关键步骤是通过形成它们的邻酰苯胺酰基来保护氨基团，然后对剩余的叔丁基酚醚单元进行ipso-硝化。与简单的N-酰基衍生物相比，这种硝化不会在邻酰苯胺基取代单元发生副反应。

  DOI：

  10.1135/cccc20041009
• 作为产物：
  描述：

  5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene 在 硝酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以12%的产率得到
  参考文献：
  名称：

  Selective ipso-nitration of tert-butylcalix[4]arene 1,3-diethers: X-ray structure of an unexpected side product

  摘要：

  1,3-Diether derivatives of tert-butylcalix[4] arene can be selectively nitrated at the para-position of the phenolic units, In this way calix[4]arenes bearing tert-butyl and nitro groups at the upper rim in alternating sequence are easily available in yields up to 75%, Ipso-attack may also occur ortho to the phenolic hydroxy group leading in a side reaction to macrocyclic compounds with two 6-nitrocyclohexa-2,4-dienone units. Both types of structures were established by single crystal X-ray analysis.

  DOI：

  10.1039/p19960001711

文献信息

• Selective Derivatization of Calix[4]arenes via Amino Groups Attached to the Wide Rim
  作者：Anca Bogdan、Myroslav O. Vysotsky、Volker Böhmer

  DOI：10.1135/cccc20041009

  日期：——

  A new strategy is proposed for the synthesis of tetraether derivatives of calix[4]arenes bearing at the wide rim nitro and phthalimido groups in well defined positions. Since both groups are precursors of amino functions, calix[4]arenes substituted by different N-acylamino residues are easily available in four steps. The essential steps during the synthesis of the precursor consist in the protection of amino groups by the formation of their phthalimides followed by ipso-nitration of the remaining tert-butylphenol ether units. This nitration occurs without side reactions at the phthalimido substituted units, in contrast to simple N-acyl derivatives.

  提出了一种新的合成策略，用于在宽口环上的特定位置引入硝基和邻酰苯胺基的卡立克斯[4]芳烃四醚衍生物。由于这两种基团都是氨基功能的前体，因此经不同的N-酰基氨基取代的卡立克斯[4]芳烃四醚很容易在四个步骤内获得。合成前体的关键步骤是通过形成它们的邻酰苯胺酰基来保护氨基团，然后对剩余的叔丁基酚醚单元进行ipso-硝化。与简单的N-酰基衍生物相比，这种硝化不会在邻酰苯胺基取代单元发生副反应。
• Selective ipso-nitration of tert-butylcalix[4]arene 1,3-diethers: X-ray structure of an unexpected side product
  作者：Oliver Mogck、Volker Böhmer、George Ferguson、Walter Vogt

  DOI：10.1039/p19960001711

  日期：——

  1,3-Diether derivatives of tert-butylcalix[4] arene can be selectively nitrated at the para-position of the phenolic units, In this way calix[4]arenes bearing tert-butyl and nitro groups at the upper rim in alternating sequence are easily available in yields up to 75%, Ipso-attack may also occur ortho to the phenolic hydroxy group leading in a side reaction to macrocyclic compounds with two 6-nitrocyclohexa-2,4-dienone units. Both types of structures were established by single crystal X-ray analysis.