3,9,12,13,16,22,25,26-octaazatricyclo[22.2.1.1^11,14]octacosa-1(27),11,14(28),24-tetraene

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,9,12,13,16,22,25,26-octaazatricyclo[22.2.1.1^11,14]octacosa-1(27),11,14(28),24-tetraene
• 英文别名: 3,9,12,13,16,22,25,26-Octazatricyclo[22.2.1.111,14]octacosa-1(26),11,14(28),24(27)-tetraene；3,9,12,13,16,22,25,26-octazatricyclo[22.2.1.111,14]octacosa-1(26),11,14(28),24(27)-tetraene
• 化学式: C₂₀H₃₆N₈
• 分子量: 388.559
• InChiKey: GSCBUUFPKQYGAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  106
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,9,12,13,16,22,25,26-octaazatricyclo[22.2.1.1^11,14]octacosa-1(27),11,14(28),24-tetraene 在 高氯酸 作用下， 以 水 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  A water molecule in the interior of a 1H-pyrazole Cu²⁺ metallocage

  摘要：

  一种吡唑环的氮杂大环Cu2+金属笼包含一个水分子，该水分子未与笼的任何受体或供体基团形成氢键。

  DOI：

  10.1039/c5nj03234b
• 作为产物：
  描述：

  3,5-(1H)-吡唑二甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 3,9,12,13,16,22,25,26-octaazatricyclo[22.2.1.1^11,14]octacosa-1(27),11,14(28),24-tetraene
  参考文献：
  名称：

  New 1H-Pyrazole-Containing Polyamine Receptors Able To Complex l-Glutamate in Water at Physiological pH Values

  摘要：

  The interaction of the pyrazole-containing macrocyclic receptors 3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1(27),11,14(28),24-tetraene 1 [L-1], 13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.111, 14] -octacosa-1(27),11,14(28),24-tetraene 2[L-2], 3,9,12,13,16,22,25,26-octaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 3[L-3], 6,19-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 4[L-4], 6,19-diphenethyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 5[L-5], and 6,19-dioctyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 6[L-6] with L-glutamate in aqueous solution has been studied by potentiometric techniques. The synthesis of receptors 3-6[L-3-L-6] is described for the first time. The potentiometric results show that 4[L-4] containing benzyl groups in the central nitrogens of the polyamine side chains is the receptor displaying the larger interaction at pH 7.4 (K-eff = 2.04 x 10(4)). The presence of phenethyl 5[L-5] or octyl groups 6[L-6] instead of benzyl groups 4[L-4] in the central nitrogens of the chains produces a drastic decrease in the stability [K-eff = 3.51 X 10(2) (5), K-eff = 3.64 x 10(2) (6)]. The studies show the relevance of the central polyaminic nitrogen in the interaction with glutamate. 1[L-1] and 2[L-2] with secondary nitrogens in this position present significantly larger interactions than 3[L-3], which lacks an amino group in the center of the chains. The NMR and modeling studies suggest the important contribution of hydrogen bonding and pi-cation interaction to adduct formation.

  DOI：

  10.1021/ja035671m

文献信息

• Cu2+-Induced formation of cage-like compounds containing pyrazole macrocycles
  作者：Francisco Escartí、Carlos Miranda、Laurent Lamarque、Julio Latorre、Enrique García-España、M. Kumar、Vicente J. Arán、Pilar Navarro

  DOI：10.1039/b110409h

  日期：2002.4.19

  The crystal structure of the complex [Cu4(H−2L)2(H2O)2(ClO4)2](ClO4)2·2H2O where L is a new pyrazole ligand containing 1,5-diaminopentane spacers represents a new form of obtaining metal ion-induced inorganic–organic cages.

  配合物[Cu4(H−2L)2(H2O)2(ClO4)2](ClO4)2·2H2O的晶体结构，其中L是含有1,5-二氨基戊烷间隔基的新型吡唑配体，代表了获得金属的新形式离子诱导的无机-有机笼。
• A water molecule in the interior of a 1H-pyrazole Cu²⁺ metallocage
  作者：Javier Pitarch-Jarque、Raquel Belda、Salvador Blasco、Pilar Navarro、Roberto Tejero、José Miguel Junquera-Hernández、Vicente Pérez-Mondéjar、Enrique García-España

  DOI：10.1039/c5nj03234b

  日期：——

  A pyrazole aza-macrocyclic Cu²⁺ metallocage shows the inclusion of a water molecule not hydrogen bonded with any acceptor or donor groups of the cage.

  一种吡唑环的氮杂大环Cu2+金属笼包含一个水分子，该水分子未与笼的任何受体或供体基团形成氢键。
• New 1<i>H</i>-Pyrazole-Containing Polyamine Receptors Able To Complex <scp>l</scp>-Glutamate in Water at Physiological pH Values
  作者：Carlos Miranda、Francisco Escartí、Laurent Lamarque、María J. R. Yunta、Pilar Navarro、Enrique García-España、M. Luisa Jimeno

  DOI：10.1021/ja035671m

  日期：2004.1.28

  The interaction of the pyrazole-containing macrocyclic receptors 3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1(27),11,14(28),24-tetraene 1 [L-1], 13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.111, 14] -octacosa-1(27),11,14(28),24-tetraene 2[L-2], 3,9,12,13,16,22,25,26-octaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 3[L-3], 6,19-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 4[L-4], 6,19-diphenethyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 5[L-5], and 6,19-dioctyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1(11,14)]-octacosa-1 (27),11,14(28),24-tetraene 6[L-6] with L-glutamate in aqueous solution has been studied by potentiometric techniques. The synthesis of receptors 3-6[L-3-L-6] is described for the first time. The potentiometric results show that 4[L-4] containing benzyl groups in the central nitrogens of the polyamine side chains is the receptor displaying the larger interaction at pH 7.4 (K-eff = 2.04 x 10(4)). The presence of phenethyl 5[L-5] or octyl groups 6[L-6] instead of benzyl groups 4[L-4] in the central nitrogens of the chains produces a drastic decrease in the stability [K-eff = 3.51 X 10(2) (5), K-eff = 3.64 x 10(2) (6)]. The studies show the relevance of the central polyaminic nitrogen in the interaction with glutamate. 1[L-1] and 2[L-2] with secondary nitrogens in this position present significantly larger interactions than 3[L-3], which lacks an amino group in the center of the chains. The NMR and modeling studies suggest the important contribution of hydrogen bonding and pi-cation interaction to adduct formation.