5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-11,23-dinitro-25,26,27,28-tetrapropoxycalix[4]arene | 201288-68-8

• 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-11,23-dinitro-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]-11,23-dinitro-25,26,27,28-tetrapropoxy-5-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]-4-N-butyl-1,3,5-triazine-2,4,6-triamine
• CAS: 201288-68-8
• 化学式: C₅₄H₇₀N₁₄O₈
• 分子量: 1043.24
• InChiKey: VNBIJXRHQUGICO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  76
• 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：
  306
• 氢给体数：
  6
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  5,17-N,N'-Bis[4-amino-6-(butylamino)-1,3,5-trazin-2-yl]diamino-11,23-dinitro-25,26,27,28-tetrapropoxycalix[4]arene 在 镍 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 5,17-Diamino-11,23-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
• 作为产物：
  描述：

  5,17-diamino-11,23-dinitro-25,26,27,28-tetrapropoxycalix[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-11,23-dinitro-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

• 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.