25,26,27,28-tetramethoxy-2-methyl-5,11,17,23-tetrakis(1,1-dimethylethyl)calix[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: 25,26,27,28-tetramethoxy-2-methyl-5,11,17,23-tetrakis(1,1-dimethylethyl)calix[4]arene
• 英文别名: 5,11,17,23-Tetratert-butyl-25,26,27,28-tetramethoxy-2-methylpentacyclo[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
• 化学式: C₄₉H₆₆O₄
• 分子量: 719.061
• InChiKey: FRPGJVXRDFHTQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 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：

  25,26,27,28-tetramethoxy-2-methyl-5,11,17,23-tetrakis(1,1-dimethylethyl)calix[4]arene 在 正丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.75h， 生成
  参考文献：
  名称：

  Easily accessible symmetrically and unsymmetrically bridge disubstituted tetrahydroxycalix[4]arenes in advantageous trans-cone conformation

  摘要：

  A new approach to symmetrically and unsymmetrically bridge disubstituted tetrahydroxycalix[4]arenes is reported involving high yields and facile workup of the products. Strong hydrogen bonds at the lower rim force the compounds to adopt the cone conformation with a trans arrangement of the bridge substituents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.101
• 作为产物：
  描述：

  5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetramethoxycalix[4]arene 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 25,26,27,28-tetramethoxy-2-methyl-5,11,17,23-tetrakis(1,1-dimethylethyl)calix[4]arene
  参考文献：
  名称：

  Easily accessible symmetrically and unsymmetrically bridge disubstituted tetrahydroxycalix[4]arenes in advantageous trans-cone conformation

  摘要：

  A new approach to symmetrically and unsymmetrically bridge disubstituted tetrahydroxycalix[4]arenes is reported involving high yields and facile workup of the products. Strong hydrogen bonds at the lower rim force the compounds to adopt the cone conformation with a trans arrangement of the bridge substituents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.101

文献信息

• Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study
  作者：Conrad Fischer、Guisheng Lin、Wilhelm Seichter、Edwin Weber

  DOI：10.1016/j.tet.2011.05.087

  日期：2011.8

  bearing various substituents including alkyl, p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkanes to give 2-alkylated calix[4]arenes or with CO2 the respective calixarene-2-carboxylic acid in good yields. A second lithiation step

  通过连续的金属化然后亲核取代，已经合成了一系列在各个亚甲基桥上带有烷基，对-溴苄基，羧基和烯丙基的取代基的杯[4]芳烃。在第一步中，单硅烷基杯[4]芳烃与末端溴代烷烃反应，以高收率得到2-烷基化杯[4]芳烃或与CO 2各自的杯芳烃-2-羧酸。单取代产物的第二次锂化步骤以及随后的极性和非极性取代基的连接产生了几种新的直径桥联二取代的杯[4]芳烃。2D-NMR测量确定双取代的杯芳烃主要采用1,2-交替解决方案中的构象。描述了新型二取代杯[4]芳烃的X射线晶体结构的第一个例子，其中杯[4]芳烃也具有罕见的1,2-交替构型。
• Synthesis of 2-Alkyl- and 2-Carboxy-<i>p</i>-<i>tert</i>-butylcalix[4]arenes via the Lithiation of Tetramethoxy-<i>p</i>-<i>tert</i>-butylcalix[4]arene
  作者：Peter A. Scully、Timothy M. Hamilton、Jordan L. Bennett

  DOI：10.1021/ol016346b

  日期：2001.8.1

  [GRAPHICS]Tetramethoxy-p-tert-butylcalix[4]arene reacts readily with ri-butyllithium to give a putative monolithiated intermediate that is substituted with alkyl halides and carbon dioxide to give in 60-75% yield conformationally mobile calix[4]arenes monosubstituted at the methylene bridge (2-position). 2-Alkyl- and 2-benzyl-substituted tetramethoxycalix[4]arenes are converted in 62-68% overall yield to the corresponding tetrahydroxy-p-tert-butylcalix[4]arenes by treatment with boron tribromide. The tetrahydroxy-p-tert-butylcalix[4]arenes exist in the cone conformation at room temperature in CDCl3 as judged by NMR spectroscopy.