5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-cyanopropyloxy)calix[4]arene | 1254972-82-1

• 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-26,27,28-trihydroxy-25-(3-cyanopropyloxy)calix[4]arene
• 英文别名: 4-[(5,11,17,23-Tetratert-butyl-26,27,28-trihydroxy-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]butanenitrile
• CAS: 1254972-82-1
• 化学式: C₄₈H₆₁NO₄
• 分子量: 716.017
• InChiKey: JQIXYIKRFMUEPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  93.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-cyanopropyloxy)calix[4]arene 在 氢氟酸 作用下， 以 苯甲醚 为溶剂， 反应 1.5h， 生成 (6S,9S,12S,15R)-9,12-dibenzyl-7,10,13-trioxo-17,21-dithia-2,8,11,14,22-pentazatricyclo[17.2.1.02,6]docosa-1(22),19-diene-15-carboxamide
  参考文献：
  名称：

  Two-Step Hantzsch Based Macrocyclization Approach for the Synthesis of Thiazole-Containing Cyclopeptides

  摘要：

  Macrocyclization via an efficient high-yielding solid-phase intramolecular thioalkylation reaction is described The reaction of S-nucleophiles with newly generated N-terminal 4-chloromethyl thiazoles led to the desired macrocyclization products 5 in high purities and good overall yields

  DOI：

  10.1021/jo1016822
• 作为产物：
  描述：

  5,11,17,23-Tetra-p-tert-butyl-25,27-bis<(cyanopropyl)oxy>-26,28-dihydroxycalix<4>arene 在 titanium(IV) chloride tetrahydrofuran 、 盐酸 、 水 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以60%的产率得到5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-cyanopropyloxy)calix[4]arene
  参考文献：
  名称：

  Easy and Selective Method for the Synthesis of Various Mono-O-functionalized Calix[4]arenes: De-O-functionalization Using TiCl₄

  摘要：

  An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized

  DOI：

  10.1021/jo101319s

文献信息

• Anionic tert-butyl-calix[4]arenes substituted at the narrow and wide rim by cobalt bis(dicarbollide)(1−) ions and CMPO-groups. Effect of stereochemistry and ratios of the functional groups on the platform on the extraction efficiency for Ln(III)/An(III)
  作者：Bohumír Grűner、Volker Böhmer、Crenguta Dordea、Pavel Selucký、Mária Bubeníková

  DOI：10.1016/j.jorganchem.2013.04.035

  日期：2013.12

  Two ionic calix[4]arenes substituted at the narrow rim with an unpaired number (n) of cobalt bis(dicarbollide)(1−) anions (1−) (n = 1 and 3) and (4 − n) CMPO groups (3c, 4c) have been synthesized via a three-step procedure based on nitrile substituted calix[4]arene precursors. Conjointly with them, the compound with a paired ratio of the groups, where n = 2 and the same substituents are located in

  两种离子杯[4]在窄边沿的取代芳烃与不成对数（Ñ钴双）（dicarbollide）（1-）阴离子（1 - ）（ñ  = 1和3）和（4 -  ñ）CMPO基（已经基于腈取代的杯[4]芳烃前体通过三步程序合成了3c，4c）。与它们结合， 报道了具有成对比率的基团的化合物，其中n = 2并且相同的取代基位于彼此相邻的1,2-位（5c）。具有成对比率的另一个化合物，但来自宽边沿系列（6c）（n 从杯[4]芳烃开始，成功地制备了＝ 2）芳烃，所述芳烃被两个硝基官能团和两个OH位点取代，可以进一步修饰。反应步骤包括：a）通过1-二恶烷衍生物[8-O（CH 2 CH 2）2 O （+） - 1,2 -C 2 B 9 H对存在于同一边缘的羟基官能团进行O-烷基化10）-（1'，2'-C 2 B 9 H 11）-3,3'-Co]（2）用作反应性结构单元，生成各自的离子腈（3a - 5a）或硝基化合物（6a））;
• Two-Step Hantzsch Based Macrocyclization Approach for the Synthesis of Thiazole-Containing Cyclopeptides
  作者：Adel Nefzi、Sergey Arutyunyan、Jason E. Fenwick

  DOI：10.1021/jo1016822

  日期：2010.11.19

  Macrocyclization via an efficient high-yielding solid-phase intramolecular thioalkylation reaction is described The reaction of S-nucleophiles with newly generated N-terminal 4-chloromethyl thiazoles led to the desired macrocyclization products 5 in high purities and good overall yields
• Easy and Selective Method for the Synthesis of Various Mono-<i>O</i>-functionalized Calix[4]arenes: De-<i>O</i>-functionalization Using TiCl₄
  作者：Joackim Bois、Jeff Espinas、Ulrich Darbost、Caroline Felix、Christian Duchamp、Denis Bouchu、Mostafa Taoufik、Isabelle Bonnamour

  DOI：10.1021/jo101319s

  日期：2010.11.19

  An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized