5,11-diamino-25,26,27,28-tetra-n-propylcalix[4]arene | 169267-32-7

• 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-diamino-25,26,27,28-tetra-n-propylcalix[4]arene
• 英文别名: 5,11-diamino-25,26,27,28-tetrapropoxycalix[4]arene；5,11-diaminocalix[4]arene；5,11-diamino-24,25,26,27-tetrapropoxycalix[4]arene；25,26,27,28-Tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-5,11-diamine；25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-5,11-diamine
• CAS: 169267-32-7
• 化学式: C₄₀H₅₀N₂O₄
• 分子量: 622.848
• InChiKey: HHEVHWHOXUCVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,11-diamino-25,26,27,28-tetra-n-propylcalix[4]arene 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-(6-aminopurin-9-yl)-N-[11-[[2-(6-aminopurin-9-yl)acetyl]amino]-25,26,27,28-tetrapropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaenyl]acetamide
  参考文献：
  名称：

  Synthesis of new calix[4]arenes containing nucleoside bases

  摘要：

  A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes 5,6 or 7 and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes 8, 9 or 10 in over 70% yield. Owing to the low solubility of adenine-N-9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated ammocalix[4]arenes derivatives 11, 12, 13 with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers 15 and 16 or 17 and 18 were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by C-13 NMR and H-1 NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00251-5
• 作为产物：
  描述：

  25,26,27,28-tetrapropyloxycalix[4]arene 在 硝酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5,11-diamino-25,26,27,28-tetra-n-propylcalix[4]arene
  参考文献：
  名称：

  A Fluorescent Probe for Al³⁺ Based on Calix[4]arene Containing Salicylaldehyde‐Derived Schiff Base

  摘要：

  摘要通过在钙[4]炔的上缘配合水杨醛衍生的希夫碱基团，制备了两种识别 Al3+ 的新型荧光探针 L1 和 L2。在这些探针中，L2 是识别 Al3+ 最有效的探针，它显示出高度选择性的荧光 "开启 "响应，发射波长为 478 nm，斯托克斯偏移为 88 nm。此外，探针 L2 还能与 Al3+ 形成 1 ：1 配位复合物，结合常数为 2.6×1010 M-1。此外，在 2.0×10-5 M 至 1.4×10-4 M 的范围内，探针 L2 的荧光强度与 Al3+ 浓度呈良好的线性关系，检测限低至 4.36×10-7 M。

  DOI：

  10.1002/ejoc.202300639

文献信息

• Calix[4]arene-porphyrin Conjugates as Versatile Molecular Receptors for Anions
  作者：Miroslav Dudič、Pavel Lhoták、Ivan Stibor、Kamil Lang、Petra Prošková

  DOI：10.1021/ol027175t

  日期：2003.1.1

  see text] Appending tetraphenylporphyrin units to the calix[4]arene skeleton via the ureido function leads to novel anion receptors designed for anion and/or cation detection by UV-vis spectroscopy. Calixarenes in the cone or 1,3-alternate conformations bearing two ureido moieties on the upper rim represent well-preorganized cavities where the anion can be held by synchronous hydrogen bonding interaction

  [结构：见正文]通过脲基官能团将四苯基卟啉单元附加到杯[4]芳烃骨架上，可得到新颖的阴离子受体，该受体设计用于通过紫外-可见光谱检测阴离子和/或阳离子。在上边缘带有两个脲基部分的圆锥形或1,3-交替构型的杯芳烃代表预先组装好的空腔，在该空腔中，阴离子可通过与NH基团的同步氢键相互作用而保持阴离子。
• Systematic approach to new ligands for anion recognition based on ureido-calix[4]arenes
  作者：Ivan Stibor、Jan Budka、Veronika Michlová、Marcela Tkadlecová、Michaela Pojarová、Petra Cuřínová、Pavel Lhoták

  DOI：10.1039/b802871k

  日期：——

  Mono, di-, tri- and tetraureido-calix[4]arenes in the cone, partial cone and 1,3-alternate conformations have been synthesised and their complexation ability towards selected anions has been studied. The structure–anion complexation ability relationship has been systematically monitored. A new type of very efficient ligands based on diureido-calix[4]arene in a 1,3-alternate conformation with pronounced bonding ability towards carboxylates was designed.

  锥形、部分锥形和1,3-交替构象的单、二、三和四脲基环[4]芳烃已被合成，并研究了它们对选定阴离子的配位能力。系统监测了结构-阴离子配位能力的关系。设计了一种新型的高效配体，其基于1,3-交替构象的二脲基环[4]芳烃，对羧酸盐具有显著的键合能力。
• Wide-rim functionalization of calix[4]arene: The di- and tetraisocyanocalix[4]arene assembling ligands and their silver(I) polymers and oligomers
  作者：Pascal Mongrain、Pierre D Harvey

  DOI：10.1139/v03-116

  日期：2003.11.1

  The 5,11- and 5,17-diisocyano-25,26,27,28-tetra-n-propoxycalix[4]arene bridging ligands (calix(NC)2) have been prepared in four steps with 34 and 30% global yields, respectively. Their corresponding Ag(I) complexes have been prepared from the direct reaction of the ligand with AgBF4 and are characterized from various spectroscopic and physical techniques. The MALDI-TOF spectra indicate the presence

  5,11- 和 5,17-二异氰基-25,26,27,28-四正丙氧基杯[4]芳烃桥连配体（杯（NC）2）分四步制备，分别为34%和30%产量，分别。它们相应的 Ag(I) 配合物是通过配体与 AgBF4 的直接反应制备的，并通过各种光谱和物理技术进行表征。MALDI-TOF 光谱表明存在Ag(calix(NC)2)(BF4)}n 类型的聚合物或低聚物。这些化合物已通过 TGA、DSC 和 XRD 进一步表征，并与低聚物种 5,11,17,23-四异氰基-25,26,27,28-四正丙氧基杯[4]芳烃银(I)进行了比较（作为 ??盐）。关键词：银，杯[4]芳烃，聚合物，异氰化物，光敏，热重分析。
• Anion-Induced Dimerization in <i>p</i>-Squaramidocalix[4]arene Derivatives
  作者：Carmine Gaeta、Carmen Talotta、Paolo Della Sala、Luigi Margarucci、Agostino Casapullo、Placido Neri

  DOI：10.1021/jo500422u

  日期：2014.4.18

  Spherical anions induce the dimerization of calix[4]arene derivatives 3 and 4 bearing squaramide moieties at the exo rim (p-squaramidocalixarenes). 1H NMR titration experiments showed that unlike the distal isomer 3, proximal p-squaramidocalixarene 4 is also able to form dimeric complexes with trigonal-planar anions.

  球形阴离子在exo边缘（p -squaramidocalixarenes）诱导杯芳烃[4]芳烃衍生物3和4带有方胺部分的二聚化。1 H NMR滴定实验表明，与远侧异构体3不同，近侧对-squaramidocalixarene 4也能够与三角平面阴离子形成二聚体络合物。
• Synthesis of potential receptor molecules by combination of upper-rim-functionalized calix[4]arenes and partly bridged resorcinarenes
  作者：Peter Timmerman、Harold Boerrigter、Willem Verboom、David N. Reinhoudt

  DOI：10.1002/recl.19951140306

  日期：——

  Combination of upper-rim-1,3-difunctionalized calix[4]arenes 14, 16, and 18 with tribridged resorcinarenes 4 and 6 and A,C-di-bridged resorcinarenes 10 and 13 yields both 1/1 calix-resorcinarenes (22–24) and 2/1 calix-resorcinarenes (25, 26). 1/1 Calix-resorcinarene 22 mainly exists as one conformer (a), but at low temperatures (−60°C) very small amounts ( < 5%) of a second conformer (b) can be observed

  上边缘1,3-双官能度杯[4]芳烃14、16和18与三桥间苯二烃4和6以及A，C-二桥间苯二酚10和13的结合产生1/1杯-间苯二烃（22 –24）和2/1杯-间苯二酚（25，26）。1/1杯型间苯二芳烃22主要作为一种构象异构体（a）存在，但是在低温（-60℃ ）下，可以观察到非常少量（＜5％）的第二种构象异构体（b）。两种构象异构体均通过绕一个C（芳烃）-N键旋转而达到平衡，并具有活化自由能（ΔG ≠）为13 kcal / mol。2/1 Calix-间苯二酚25和26更具柔韧性，并且以构象异构体的混合物形式存在。为了能够通过杯[4]芳烃片段之间的刚性间隔基来刚性化2/1杯-间芳烃芳烃的结构，合成了带有硝基，羧基的1,3-二氨基杯[4]芳烃衍生物31、32和34酯和未取代的芳环上的氰基。利用这些杯[4]芳烃衍生物，合成了三个新的功能化的2/1杯-间苯二碳烯芳烃35-37。