5,17-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene | 1078151-72-0

• 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-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene
• 英文别名: 5,17-diamino-25,26,27,28-tetrapropoxycalix[4]arene；5,17-diamino-25,26,27,28-tetra-n-propyloxycalix[4]arene；25,26,27,28-tetrapropoxypentacyclo[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-dodecaene-5,17-diamine
• CAS: 1078151-72-0
• 化学式: C₄₀H₅₀N₂O₄
• 分子量: 622.848
• InChiKey: VYVMNSKCVGCAFZ-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：

  5,17-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene 在 氨 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 bis(chlorotriazine)
  参考文献：
  名称：

  Noncovalent Assembly of Functional Groups on Calix[4]Arene Molecular Boxes

  摘要：

  AbstractCalix[4]arenes diametrically substituted at the upper rim with two melamine units spontaneously form well‐defined box‐like assemblies in the presence of two equivalents of 5,5‐diethylbarbituric acid. These assemblies, consisting of nine different components, are held together by 36 hydrogen bonds and are stable in apolar solvents at concentrations of up to 10−4M. This paper reports the first X‐ray crystal structure, and the MALDI TOF mass spectra together with the complete 1H NMR spectroscopic characterization of these hydrogen‐bonded assemblies. The crystal structure clearly shows that the assemblies are stereogenic, as a result of the antiparallel orientation of the two rosette motifs. Furthermore, the synthesis of twelve new 1,3‐bis(melamine)calix[4]arenes carrying different numbers and types of functionalities at the upper rim is described. Detailed 1H NMR spectroscopic studies on the assembly behavior of these functionalized calix[4]arenes shows that 1) polar substituents (e.g. nitro, cyano) hardly affect the stability of the hydrogen‐bonded assembly; 2) hydrogen bond donating or accepting groups, like amino and acetamido, can disturb assembly of the boxes under certain conditions by destabilizing the calix[4]arene pinched cone conformation as a result of intramolecular hydrogen bond formation; and 3) sterically bulky groups (e.g. tBu) can significantly inhibit the formation of the hydrogen‐bonded assembly, but this effect very much depends on the exact positions of the groups.

  DOI：

  10.1002/chem.19970031115
• 作为产物：
  描述：

  5,17-dibromo-25,26,27,28-tetra-n-propylcalix[4]arene 在 copper(I) oxide 、 一水合肼 作用下， 以 2,4,6-三甲基吡啶 、 乙醇 为溶剂， 反应 98.0h， 生成 5,17-diamino-25,26,27,28-tetrakis(propyloxy)calix[4]arene
  参考文献：
  名称：

  杯[4]芳烃的宽边功能化：二和四异氰杯[4]芳烃组装配体及其银（I）聚合物和低聚物

  摘要：

  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BF4??盐）。关键词：银，杯[4]芳烃，聚合物，异氰化物，光敏，热重分析。

  DOI：

  10.1139/v03-116

文献信息

• Multiple Cycloadditive Macrocyclization: An Efficient Method for Crown Ether-Type Cyclophanes, Bis-Calix[4]arenes and Silamacrocycles
  作者：Byeang Hyean Kim、Eun Jeong Jeong、Gil Tae Hwang、Natarajan Venkatesan

  DOI：10.1055/s-2001-18061

  日期：——

  Macrocycles constitute a broad spectrum of compounds, which play a significant role in host-guest supramolecular chemistry. We have rationally designed an efficient novel synthetic method to synthesize different types of artificial receptive macrocycles containing isoxazoline or isoxazole ring systems. This method involves multiple (double, triple or quadruple) cycloadditions between bifunctional dipoles and bifunctional dipolarophiles. We have presented our synthetic results to show the ease with which this one-pot synthetic method can be extended to synthesize different types of macrocycles such as cyclophanes, bis-calix[4]arenes and silamacrocycles. Hence, with appropriate combination of bifunctional dipoles and bifunctional dipolarophiles, the ring size of macrocycles could be controlled. This multiple cycloadditive macrocyclization will be a useful arsenal for the synthesis of various macrocycles.

  大环化合物构成了广泛的一类化合物，在主客体超分子化学中发挥着重要作用。我们合理设计了一种高效的新型合成方法，用于合成含有异噁唑啉或异噁唑环系的人工受体大环。该方法涉及双功能亲电试剂与双功能亲双烯体之间的多次（双、三或四重）环加成反应。我们展示了合成结果，表明这种一锅法合成方法可以轻松扩展，用于合成不同类型的大环，如环芳烷、双杯[4]芳烃和大环硅烷。因此，通过适当组合双功能亲双烯体和双功能亲电试剂，可以控制大环的环尺寸。这种多次环加成大环化将为合成各种大环提供有用的工具。
• Hexameric assembly of 5,17-di-substituted calix[4]arene in the solid state
  作者：Yutaro Yamasaki、Ryo Sekiya、Takeharu Haino

  DOI：10.1039/c7ce01515a

  日期：——

  form a chiral hexagonal channel, which is a rare example of calix[4]arene derivatives in the solid state. The fact that the branched guest (2-PrOH) and the racemic mixture of the host formed different crystal packings wherein no hexameric structure existed indicates that both the linearity of the guest and the homochirality of the host are important factors for driving the columnar structures to form

  拥有（S）-扁桃酰胺臂（（S，S）-1）的手性5,17-双官能化25,26,27,28-四丙基氧基杯[4]芳烃提供共结晶（S，S）-1（溶剂）（溶剂＝ MeOH，EtOH，1-PrOH，2-PrOH和CH 3 CN）。X射线衍射分析表明，（S，S）-1形成了从头到尾的柱状结构。在大多数共晶体中（MeOH，EtOH，1-PrOH和CH 3CN），将柱状结构以六聚体形式排列以形成手性六边形通道，这是固态杯中杯[4]亚芳基衍生物的一个罕见例子。支化的客体（2-PrOH）与主体的外消旋混合物形成不同的晶体堆积（其中不存在六聚体结构）这一事实表明，客体的线性和主体的同手性都是驱动柱状结构转化为碳原子的重要因素形成六聚体装配体。载脂蛋白（S，S）-1载脂蛋白表现出有趣的吸附行为; 它在测试的有机分子中吸附了苯。重复几次吸附和解吸过程，证明了（S，S）-1个载脂蛋白。
• 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。
• Synthesis and Conformational Characteristics of Calix[4]arene Oligomers
  作者：Masayuki Morie、Ryo Sekiya、Takeharu Haino

  DOI：10.1246/bcsj.20210287

  日期：2021.11.15

  of calix[4]arene realized a variety of calix[4]arene systems. Compared to these monomeric calix[4]arenes, covalently linked calix[4]arene oligomers have not been studied well. Calix[4]arene oligomers can be utilized as building blocks of supramolecular complexes as well as for the synthesis of calix[4]arene polymers. This background motivated us to develop synthetic procedures for calix[4]arene oligomers

  杯[4]芳烃的下缘和/或上缘功能化实现了多种杯[4]芳烃系统。与这些单体杯[4]芳烃相比，共价连接的杯[4]芳烃低聚物尚未得到很好的研究。杯[4]芳烃低聚物可用作超分子复合物的构建单元以及杯[4]芳烃聚合物的合成。这一背景促使我们开发杯[4]芳烃低聚物的合成程序并对这些低聚物进行构象分析。我们生产从单体到五聚体的低聚物。五聚体与 2,3-二苄氧基-1,4-苯二甲酸的偶联可以得到十聚体和低聚物。NMR测量，X射线晶体结构分析，