5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-25,26,27,28-tetrapropoxycalix[4]arene | 471257-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-25,26,27,28-tetrapropoxycalix[4]arene
• 英文别名: 2-N-[17-[[4-amino-6-(butylamino)-1,3,5-triazin-2-yl]amino]-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]-4-N-butyl-1,3,5-triazine-2,4,6-triamine
• CAS: 471257-88-2；201288-64-4
• 化学式: C₅₄H₇₂N₁₂O₄
• 分子量: 953.244
• InChiKey: URIPLUYNRKMQGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  214
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5,5-二乙基丙二酰脲 、 5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-25,26,27,28-tetrapropoxycalix[4]arene 以 氘代氯仿 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Selective Self-Organization of Guest Molecules in Self-Assembled Molecular Boxes

  摘要：

  This article describes the synthesis and binding properties of highly selective noncovalent molecular receptors 1(3).(DEB)(6) and 3(3).(DEB)(6) for different hydroxyl functionalized anthraquinones 2. These receptors are formed by the self-assembly of three calix[4]arene dimelamine derivative molecules (11 or 3) and six diethyl barbiturate (DEB) molecules to give 1(3).(DEB)(6) or 3(3).(DEB)(6). Encapsulation of 2 occurs in a highly organized manner; that is, a noncovalent hydrogen-bonded trimer of 2 is formed within the hydrogen-bonded receptors 1(3).(DEB)(6) and 3(3).(DEB)(6). Both receptors 1(3).(DEB)(6) and 3(3).(DEB)(6) change conformation from staggered to eclipsed upon complexation to afford a better fit for the 23 trimer. The receptor selectivity toward different anthraquinone derivatives 2 has been studied using H-1 NMR spectroscopy, X-ray crystallography, UV spectroscopy, and isothermal microcalorimetry (ITC). The pi-pi stacking between the electron-deficient center ring of the anthraquinone derivatives 2a-c and 2e-g and the relatively electron-poor melamine units of the receptor is the driving force for the encapsulation of the guest molecules. The selectivity of the hydrogen-bonded host for the anthraquinone derivatives is the result of steric interactions between the guest molecules and the calix[4]arene aromatic rings of the host.

  DOI：

  10.1021/ja0536973
• 作为产物：
  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 5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-25,26,27,28-tetrapropoxycalix[4]arene
  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

文献信息

• Self-Assembly of Polar Functionalities Using Noncovalent Platforms
  作者：Jessica M. C. A. Kerckhoffs、Mercedes Crego-Calama、Ingrid Luyten、Peter Timmerman、David N. Reinhoudt

  DOI：10.1021/ol000244o

  日期：2000.12.1

  [GRAPHICS]Small peptide fragments functionalized with dimelamine units spontaneously form well-defined assemblies. The hydrogen-bond donating and accepting sites in the peptide units are perfectly compatible with the hydrogen-bond assembly motif and slightly stabilize the assembly via additional hydrogen bond formation.
• Selective Self-Organization of Guest Molecules in Self-Assembled Molecular Boxes
  作者：Jessica M. C. A. Kerckhoffs、Mattijs G. J. ten Cate、Miguel A. Mateos-Timoneda、Fijs W. B. van Leeuwen、Bianca Snellink-Ruël、Anthony L. Spek、Huub Kooijman、Mercedes Crego-Calama、David N. Reinhoudt

  DOI：10.1021/ja0536973

  日期：2005.9.1

  This article describes the synthesis and binding properties of highly selective noncovalent molecular receptors 1(3).(DEB)(6) and 3(3).(DEB)(6) for different hydroxyl functionalized anthraquinones 2. These receptors are formed by the self-assembly of three calix[4]arene dimelamine derivative molecules (11 or 3) and six diethyl barbiturate (DEB) molecules to give 1(3).(DEB)(6) or 3(3).(DEB)(6). Encapsulation of 2 occurs in a highly organized manner; that is, a noncovalent hydrogen-bonded trimer of 2 is formed within the hydrogen-bonded receptors 1(3).(DEB)(6) and 3(3).(DEB)(6). Both receptors 1(3).(DEB)(6) and 3(3).(DEB)(6) change conformation from staggered to eclipsed upon complexation to afford a better fit for the 23 trimer. The receptor selectivity toward different anthraquinone derivatives 2 has been studied using H-1 NMR spectroscopy, X-ray crystallography, UV spectroscopy, and isothermal microcalorimetry (ITC). The pi-pi stacking between the electron-deficient center ring of the anthraquinone derivatives 2a-c and 2e-g and the relatively electron-poor melamine units of the receptor is the driving force for the encapsulation of the guest molecules. The selectivity of the hydrogen-bonded host for the anthraquinone derivatives is the result of steric interactions between the guest molecules and the calix[4]arene aromatic rings of the host.
• Noncovalent Assembly of Functional Groups on Calix[4]Arene Molecular Boxes
  作者：Peter Timmerman、Remko H. Vreekamp、Ron Hulst、Willem Verboom、David N. Reinhoudt、Kari Rissanen、Konstantin A. Udachin、John Ripmeester

  DOI：10.1002/chem.19970031115

  日期：1997.11

  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.