5,17-bis(aminomethyl)-25,26,27,28-tetra-n-propoxy-calix[4]arene | 950744-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,17-bis(aminomethyl)-25,26,27,28-tetra-n-propoxy-calix[4]arene
• 英文别名: [17-(Aminomethyl)-25,26,27,28-tetrapropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]methanamine
• CAS: 950744-69-1
• 化学式: C₄₂H₅₄N₂O₄
• 分子量: 650.902
• InChiKey: QMOQRPRDNVYQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  硫代异氰酸苯酯 、 5,17-bis(aminomethyl)-25,26,27,28-tetra-n-propoxy-calix[4]arene 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到5,17-bis<(N'-phenyl(thio)ureido)methyl>-25,26,27,28-tetrakis(1-propyloxy)calix<4>arene
  参考文献：
  名称：

  Casnati, Alessandro; Fochi, Mariacristina; Minari, Patrizia, Gazzetta chimica Italiana, 1996, vol. 126, # 2, p. 99 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  25,27-dipropyloxy-5,17-diformylcalix[4]arene 在 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 硼烷 、 sodium hydride 、 一水合肼 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 87.0h， 生成 5,17-bis(aminomethyl)-25,26,27,28-tetra-n-propoxy-calix[4]arene
  参考文献：
  名称：

  Casnati, Alessandro; Fochi, Mariacristina; Minari, Patrizia, Gazzetta chimica Italiana, 1996, vol. 126, # 2, p. 99 - 106

  摘要：

  DOI：

文献信息

• Synthesis of Novel Macrocyclic Peptido-calix[4]arenes and Peptidopyridines as Precursors for Potential Molecular Metallacages, Chemosensors and Biologically Active Candidates
  作者：Abd El-Galil El-Sayed Amr、Mohamed Abo-Ghalia、Mohamed M. Abdalah

  DOI：10.1515/znb-2006-1104

  日期：2006.11.1

  Novel macrocyclic dipicolinic acid acylated peptides based on upper rim bridged peptidocalix[ 4]arenes, peptido-pyridines or hybrid structures of both, were synthesized as potential molecular metallacages and chemosensors. While conventional azide or mixed anhydride (ethyl chloroformate) peptide couplings served well for assembling the L-tyrosine or L-ornithine peptide backbones, the acid chloride of pyridine-2,6-dicarboxylic acid (dipicolinic acid) acid served as the complementary acylating agent. The structure assignment of the new compounds was based on chemical and spectroscopic evidences. Some of these compounds exhibit antimicrobial activities.

  基于上缘桥联的肽联四醚，肽-吡啶或两者混合结构的新型大环二吡啯酸酰化肽被合成为潜在的分子金属笼和化学传感器。传统的叠氮或混合酸酐（氯甲酸乙酯）肽偶联反应可用于组装L-酪氨酸或L-鸟氨酸肽骨架，而吡啶-2,6-二羧酸（二吡啯酸）的酸氯化物则用作补充酰化试剂。新化合物的结构鉴定基于化学和光谱证据。其中一些化合物表现出抗菌活性。
• Anion receptors based on intramolecularly bridged calix[4]arenes bearing ureido functions
  作者：Markéta Řezanková、Jan Budka、Jiří Mikšátko、Václav Eigner、Ivana Císařová、Petra Cuřínová、Pavel Lhoták

  DOI：10.1016/j.tet.2016.12.054

  日期：2017.2

  A novel type of anion receptor, based on the intramolecularly bridged calix[4]arene immobilized in the cone conformation, is described. The reductive coupling of a distal dialdoxime using Zn/TiCl4 led to calix[4]arene with a meso-1,2-diaminoethane-1,2-diyl bridge that was transformed into the corresponding receptors by reaction with aryl isocyanates. 1H NMR titration experiments revealed that the combination

  描述了一种新型的阴离子受体，其基于分子内桥联的杯[4]芳烃固定在圆锥构象上。使用Zn / TiCl 4的远端二氧肟肟的还原偶联导致杯[4]芳烃与内消旋-1，2-二氨基乙烷-1，2，2-二芳基桥基通过与芳基异氰酸酯反应转化为相应的受体。1 H NMR滴定实验表明，独特的结构特征（桥）与芳基脲基官能团的组合导致形成非常有效的阴离子受体。相反，非桥连化合物进行建模，这些公预组织受体可以有效地结合选定的阴离子（H 2 PO 4 -，ACO -，BZO−）即使在竞争激烈的溶剂（DMSO- d 6）中也可以通过氢键相互作用。
• Synthesis of Some New Chiral Tricyclic and Macrocyclic Pyridine Derivatives as Antimicrobial Agents
  作者：Abd El-Galil E. Amr、Ashraf M. Mohamed、Alhussein A. Ibrahim

  DOI：10.1515/znb-2003-0908

  日期：2003.9.1

  A series of chiral macrocyclic pyridines has been prepared starting from N²,N²-(pyridine- 2,6-dicarbonyl)diamino acid hydrazides (2a-c) and N,N-bis-(1-carboxy-2-substituted)-2,6- diaminocarbonyl)pyridines (3a,b). The coupling of (2a-c) with 2,6-pyridine dicarbonyldichloride (4) gave the compounds (5a-c). Compounds 2a-c were coupled with 2,6-diacetylpyridine (6) to yield compounds (7a-c) and with heterocyclic aldehydes (8) or (10) to give the compounds (9a-c) or (11a-c). In addition, the hydrazides (2a-c) were reacted with diformylcalix[4]arene 12 to afford the macrocyclic calix[4]arene hydrazone derivatives (13a-c) in reasonable yields. Finally, reaction of diaminocalix-[4]arene derivatives (14a,b) with hydrazides 2a,b or acids (3a,b), using azide or mixed anhydride methods afforded macrocyclic calix[4]arene derivatives 15a,b and 16a,b, respectively. The structure assignments of the new compounds are based on chemical and spectroscopic evidence. The biological activity screening tests showed that many of the obtained compounds exhibit high antimicrobial activity comparable to ampicillin and chloramphenicol which are used as reference compounds.

  一系列手性大环吡啶化合物是从N^2,N^2-(吡啶-2,6-二羧基)二氨基酸脒酰肼（2a-c）和N,N-双-(1-羧基-2-取代基)-2,6-二氨基羧基）吡啶（3a,b）出发制备的。将（2a-c）与2,6-吡啶二羧酰二氯化物（4）偶联得到化合物（5a-c）。将化合物2a-c与2,6-二乙酰基吡啶（6）偶联得到化合物（7a-c），与杂环醛（8）或（10）偶联得到化合物（9a-c）或（11a-c）。此外，将脒酰肼（2a-c）与二甲酰基杯[4]芳烃12反应，以合理产率得到大环杯[4]芳烃脒肼衍生物（13a-c）。最后，将二氨基杯[4]芳烃衍生物（14a,b）与脒酰肼2a,b或酸（3a,b）反应，使用叠氮化物或混合酐方法得到大环杯[4]芳烃衍生物15a,b和16a,b，分别。这些新化合物的结构鉴定基于化学和光谱证据。生物活性筛选测试显示，许多获得的化合物表现出高抗菌活性，与作为参考化合物的氨苄青霉素和氯霉素相媲美。
• Calix[4]arene based α-aminophosphonates: Novel carriers for zwitterionic amino acids transport
  作者：Igor S. Antipin、Ivan I. Stoikov、Evgueni M. Pinkhassik、Nataly A. Fitseva、Ivan Stibor、Alexander I. Konovalov

  DOI：10.1016/s0040-4039(97)01305-1

  日期：1997.8

  a series of calix[4]arene based α-aminophosphonates were synthesized by the Kabachnik-Fields reaction of the calixarene-diamine (either at lower or upper rim), diethyl phosphite and a carbonyl compound (acetone or cyclohexanone). These compounds exhibited remarkable selectivity as carriers for the membrane transport of the zwitterionic form of aromatic amino acids.

  通过杯芳烃-二胺（上下边缘），亚磷酸二乙酯和羰基化合物（丙酮或环己酮）的Kabachnik-Fields反应，合成了一系列杯芳烃[4]芳烃基的α-氨基膦酸酯。这些化合物作为两性离子形式的芳香族氨基酸膜运输的载体表现出显着的选择性。
• Synthesis of New Chiral Ligands by Capping of Calix[4]arene Derivatives
  作者：Evgueni Pinkhassik、Ivan Stibor、Vladimír Havlíček

  DOI：10.1135/cccc19961182

  日期：——

  Calix[4]arene derivatives are used as a scaffold for the attachment of chiral substituents. Calix[4]arenes having either lower or upper rim capped with chiral binaphtholic species 5 and 6, as well as new biscalix[4]arenodiaza-18-crown-6 (8), have been synthesized.

  Calix[4]芳烃衍生物被用作连接手性取代基的支架。已合成具有手性双萘基物种5和6的下缘或上缘被封顶的Calix[4]芳烃，以及新的双Calix[4]芳烃二氮杂18-冠-6（8）。