5,11,17,23-Tetra-p-tert-butyl-25,26,27,28-tetrakis<(aminobutyl)oxy>calix<4>arene | 166804-12-2

• 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-p-tert-butyl-25,26,27,28-tetrakis<(aminobutyl)oxy>calix<4>arene
• 英文别名: 7,13,19,25-tetra-tert-butyl-27,28,29,30-tetra[(4-aminobutyl)-oxy]-2,3-dihomo-3-oxacalix[4]arene；5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[(4-amino)butoxy]calix[4]arene；5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(aminobutoxy)calix[4]arene；25,26,27,28-tetrakis(4-aminobutoxy)p-tert-butylcalix[4]arene；tetrakis 4-(amino-butoxy)-p-tert butyl calix[4]arene；5,11,17,23-Tetra-p-tert-butyl-25,26,27,28-tetrakis[(aminobutyl)oxy]calix[4]arene；4-[[26,27,28-Tris(4-aminobutoxy)-5,11,17,23-tetratert-butyl-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]butan-1-amine
• CAS: 166804-12-2
• 化学式: C₆₀H₉₂N₄O₄
• 分子量: 933.415
• InChiKey: CIAWVXZMGWBOHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-Tetra-p-tert-butyl-25,26,27,28-tetrakis<(aminobutyl)oxy>calix<4>arene 以40%的产率得到
  参考文献：
  名称：

  Scheerder Jurgen, Fochi Mariacristina, Engbersen Johan F. J., Reinhoudt D+, J. Org. Chem, 59 (1994) N 25, S 7815-7820

  摘要：

  DOI：
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 sodium tetrahydroborate 、 sodium hydride 、 potassium carbonate 、 cobalt(II) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 169.0h， 生成 5,11,17,23-Tetra-p-tert-butyl-25,26,27,28-tetrakis<(aminobutyl)oxy>calix<4>arene
  参考文献：
  名称：

  Urea-Derivatized p-tert-Butylcalix[4]arenes: Neutral Ligands for Selective Anion Complexation

  摘要：

  Functionalization of the lower rim of p-tert-butylcalix[4]arene with four (thio)urea groups, results in a class of receptors selective for spherical onions that-are bound exclusively through hydrogen bonding. H-1 NMR spectroscopy in CDCl3 reveals a selectivity for Cl- over Br- and I-. The stoichiometry is 1:1 in all cases as was confirmed by Job plots. The association constants are strongly dependent on the nature of the substituent at the urea moiety. The bidentate phenylurea derivative 9 shows the strongest complexation (K-ass. Cl- = 7.1 x 10(3) M(-1)) and the largest selectivity for Cl-.

  DOI：

  10.1021/jo00104a044

文献信息

• Synthesis of multivalent oxamate ligands based on calix[4]arene and thiacalix[4]arene backbones in 1,3-Alternate conformation
  作者：Mohamed Habib Noamane、Sylvie Ferlay、Rym Abidi、Mir Wais Hosseini

  DOI：10.1016/j.tet.2017.05.043

  日期：2017.7

  Five new multivalent ligands based on either p-tert-butylthiacalix[4]arene (TCA) 1 or p-tert-butylcalix[4]arene (CA) 2 backbones in 1,3-Alternate conformation bearing four oxamate coordinating groups at their lower rim were designed and synthesized by a multistep strategy. These ligands differ either by the nature of the calix[4]arene backbone (CA or TCA) or by the nature of the spacer ((CH2)n) connecting

  根据任一五个新多价配体对叔丁基硫杂杯[4]芳烃（TCA）1或对-叔丁基lcalix [4]芳烃（CA）2个主链中的1,3- -Alternate构象轴承4个草氨酸盐配位基团在他们的下轮圈是通过多步策略设计和合成的。这些配体的不同之处在于杯[4]芳烃骨架（CA或TCA）的性质，或将草酸酯结合单元连接至骨架的间隔基（（CH 2）n）的性质。
• Calixarene-Based Picolinamide Extractants for Selective An/Ln Separation from Radioactive Waste
  作者：Alessandro Casnati、Nicola Della Ca'、Marco Fontanella、Francesco Sansone、Franco Ugozzoli、Rocco Ungaro、Karine Liger、Jean-Francois Dozol

  DOI：10.1002/ejoc.200400793

  日期：2005.6

  Eleven novel ligands having picolinamide or thiopicolinamide binding groups at the upper or lower rim of calix[4]-, calix[6]- and calix[8]arenes have been synthesised. The conformational properties of some of these ligands were studied in solution by means of NMR spectroscopy and in the solid state by X-ray diffraction. Their ability to extract AmIII or EuIII from water to NPHE (o-nitrophenyl hexyl

  已经合成了 11 种在杯[4]-、杯[6]-和杯[8]芳烃的上缘或下缘具有吡啶甲酰胺或硫代吡啶酰胺结合基团的新型配体。这些配体中的一些的构象特性在溶液中通过核磁共振光谱法和在固态下通过 X 射线衍射进行研究。在不同浓度的 LiNO3、HNO3 和亲脂性二碳化物阴离子 (BrCosan) 下测试了它们从水中提取 AmIII 或 EuIII 到 NPHE（邻硝基苯基己基醚）的能力。与使用模型配体 N-丁基吡啶甲酰胺 (19) 获得的数据相比，数据显示杯芳烃配体的结合位点之间的高度合作。其中一些配体显示出非常高的 Am3+ 分配系数 (DAm > 300)，并且在 pH ≥ 3 时具有良好的 Am/Eu 选择性，这为它们在处理低酸度放射性废物中的应用开辟了有趣的前景。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Calixarene derivatives
  申请人：Commissariat a l'Energie Atomique

  公开号：US06657081B1

  公开（公告）日：2003-12-02

  The invention relates to new calixarenes according to the formula: wherein: R1 is an alkyl or aryl group, or a hydrogen atom, R2 and R3, which may be identical or different, are alkyl or aryl groups, n is an integer ranging from 2 to 8, and p is an integer ranging from 4 to 8. Said calixarenes may be used to extract actinides and lanthanides from aqueous solutions.

  该发明涉及新的杯芳烃，其化学式如下：其中：R1是烷基或芳基基团，或氢原子，R2和R3可以相同也可以不同，是烷基或芳基基团，n是2到8之间的整数，p是4到8之间的整数。该杯芳烃可用于从水溶液中提取锕系元素和镧系元素。
• Amphiphilic Guanidinocalixarenes Inhibit Lipopolysaccharide (LPS)- and Lectin-Stimulated Toll-like Receptor 4 (TLR4) Signaling
  作者：Stefania E. Sestito、Fabio A. Facchini、Ilaria Morbioli、Jean-Marc Billod、Sonsoles Martin-Santamaria、Alessandro Casnati、Francesco Sansone、Francesco Peri

  DOI：10.1021/acs.jmedchem.7b00095

  日期：2017.6.22

  optimized to dock into MD-2 and CD14 binding sites. Some of these calixarenes were active in inhibiting, in a dose-dependent way, the LPS-stimulated TLR4 activation and TLR4-dependent cytokine production in human and mouse cells. Moreover, guanidinocalixarenes also inhibited TLR4 signaling when TLR4 was activated by a non-LPS stimulus, the plant lectin PHA. While the activity of guanidinocalixarenes

  我们最近报道了阳离子两亲物在抑制TLR4活化以及随后在细胞和动物模型中产生炎性细胞因子的活性。从适当设计的阳离子两亲物可以充当CD14 / MD-2配体并因此调节TLR4信号的假设出发，我们在此介绍一组两亲性胍基杯芳烃，其结构在计算上经过优化，可与MD-2和CD14结合位点对接。这些杯芳烃中的一些在以剂量依赖性方式抑制人和小鼠细胞中LPS刺激的TLR4活化和TLR4依赖性细胞因子产生方面具有活性。此外，当TLR4被非LPS刺激（植物凝集素PHA）激活时，胍基杯芳烃也抑制TLR4信号传导。
• Selective Binding of Spherical and Linear Anions by Tetraphenyl(thio)urea-Based Dihomooxacalix[4]arene Receptors
  作者：Filipa A. Teixeira、Paula M. Marcos、José R. Ascenso、Giovanna Brancatelli、Neal Hickey、Silvano Geremia

  DOI：10.1021/acs.joc.7b01801

  日期：2017.11.3

  dihomooxacalix[4]arene anion receptors (phenylurea 4a, phenylthiourea 4b, and tert-butylurea 4c) were synthesized and obtained in the cone conformation in solution, as shown by NMR studies. The X-ray crystal structure of 4c is reported. The host–guest properties of these receptors toward several anions were investigated by 1H NMR titrations. Phenylurea 4a displayed a very efficient binding toward the spherical

  合成了三种新颖的四（硫）脲基二高氧杂lix [4]芳烃阴离子受体（苯基脲4a，苯基硫脲4b和叔丁基脲4c），并在溶液中呈锥形构象，如NMR研究所示。报告了4c的X射线晶体结构。通过1 H NMR滴定研究了这些受体对几种阴离子的主客体性质。苯基脲图4a中显示的非常有效的朝向球形F结合- Cl和-的阴离子，及所述线性CN - （日志ķ屁股分别为3.46、3.50和4.02）。与相关的双齿苯基脲二高氧杂acalix [4]芳烃相比，四苯基脲4a的预组织性更高，氢键供体位点的数量更高，其结合效率显着提高。