3-phenethyl-1,5-diphthalimido-3-azapentane | 661486-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-phenethyl-1,5-diphthalimido-3-azapentane
• CAS: 661486-68-6
• 化学式: C₂₈H₂₅N₃O₄
• 分子量: 467.524
• InChiKey: NZMJWUVDJJZBBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-phenethyl-1,5-diphthalimido-3-azapentane 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以57%的产率得到N,N-bis-(2-aminoethyl)-2-phenylethylamine
  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
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 100.0h， 生成 3-phenethyl-1,5-diphthalimido-3-azapentane
  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