N,N,N,N',N',N'-hexamethylnonane-1,9-diammonium dibromide | 56971-27-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,N,N',N',N'-hexamethylnonane-1,9-diammonium dibromide
• 英文别名: hexa-N-methyl-N,N'-nonanediyl-di-ammonium; dibromide；Hexa-N-methyl-N,N'-nonandiyl-di-ammonium; Dibromid
• CAS: 56971-27-8
• 化学式: 2Br*C₁₅H₃₆N₂
• 分子量: 404.272
• InChiKey: SWYVANMLSNTXGK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  N,N,N,N',N',N'-hexamethylnonane-1,9-diammonium dibromide 、 α-环糊精 以 重水 为溶剂， 生成
  参考文献：
  名称：

  Kinetics of the self-assembly of bold alpha -cyclodextrin [2]pseudorotaxanes with polymethylene threads bearing quaternary ammonium and phosphonium end groups

  摘要：

  The kinetics and mechanism of the formation and dissociation of a series of [2]pseudorotaxanes, comprised of or-cyclodextrin (alpha-CD) as the cyclic component and the ([Me3N(CH2)(n)NMe3](2+) (n = 8-12), [Me2EtN(CH2)(10)NEtMe2](2+), and [Me3P(CH2)(10)PMe3](2+)) dications as the threads, were determined by means of H-1 and P-31 NMR in aqueous solution. The length of the polymethylene chain (n) of the thread, which has a minor effect on the rate constant for pseudorotaxane formation, is important in the kinetics of the dissociation reactions, with the longer, more hydrophobic chains resulting in slower pseudorotaxane dissociation. The replacement of one methyl substitutent by an ethyl group in each of the end groups on the [Me3N(CH2)(10)NMe3](2+) thread results in a 30-fold decrease in the formation rate constant. Replacements, by ethyls, of two or all of the methyl substitutents prevent the formation of the pseudorotaxane, even after prolonged heating. The pseudorotaxane containing the {Me3P(CH2)(10)PMe3 .alpha-CD}(2+) thread forms only at elevated temperatures by a slippage mechanism, and the rate constant for its self-assembly at 75 degrees C (8 x 10(-5) M-1 s(-1)) is more than 10(6) smaller than the rate constant at 75 degrees C (200 M-1 s(-1)) extrapolated for the corresponding {Me3N(CH2)(10)NMe3.alpha-CD}(2+) complex. The enthalpies and entropies of activation for the formation and dissociation of the [2]pseudorotaxanes decrease with an increase in the size and hydrophobicity of the end groups, suggesting a reduced role of desolvation of the quaternized atoms in the threading or dethreading processes.

  DOI：

  10.1139/cjc-76-6-843
• 作为产物：
  描述：

  以 重水 为溶剂， 生成 N,N,N,N',N',N'-hexamethylnonane-1,9-diammonium dibromide 、 α-环糊精
  参考文献：
  名称：

  Kinetics of the self-assembly of bold alpha -cyclodextrin [2]pseudorotaxanes with polymethylene threads bearing quaternary ammonium and phosphonium end groups

  摘要：

  The kinetics and mechanism of the formation and dissociation of a series of [2]pseudorotaxanes, comprised of or-cyclodextrin (alpha-CD) as the cyclic component and the ([Me3N(CH2)(n)NMe3](2+) (n = 8-12), [Me2EtN(CH2)(10)NEtMe2](2+), and [Me3P(CH2)(10)PMe3](2+)) dications as the threads, were determined by means of H-1 and P-31 NMR in aqueous solution. The length of the polymethylene chain (n) of the thread, which has a minor effect on the rate constant for pseudorotaxane formation, is important in the kinetics of the dissociation reactions, with the longer, more hydrophobic chains resulting in slower pseudorotaxane dissociation. The replacement of one methyl substitutent by an ethyl group in each of the end groups on the [Me3N(CH2)(10)NMe3](2+) thread results in a 30-fold decrease in the formation rate constant. Replacements, by ethyls, of two or all of the methyl substitutents prevent the formation of the pseudorotaxane, even after prolonged heating. The pseudorotaxane containing the {Me3P(CH2)(10)PMe3 .alpha-CD}(2+) thread forms only at elevated temperatures by a slippage mechanism, and the rate constant for its self-assembly at 75 degrees C (8 x 10(-5) M-1 s(-1)) is more than 10(6) smaller than the rate constant at 75 degrees C (200 M-1 s(-1)) extrapolated for the corresponding {Me3N(CH2)(10)NMe3.alpha-CD}(2+) complex. The enthalpies and entropies of activation for the formation and dissociation of the [2]pseudorotaxanes decrease with an increase in the size and hydrophobicity of the end groups, suggesting a reduced role of desolvation of the quaternized atoms in the threading or dethreading processes.

  DOI：

  10.1139/cjc-76-6-843

文献信息

• Barlow; Ing, British Journal of Pharmacology and Chemotherapy, 1948, vol. 3, p. 300
  作者：Barlow、Ing

  DOI：——

  日期：——
• The bisnaphthalimides as new active lead compounds against Plasmodium falciparum
  作者：Maximilian Tischer、Ludmilla Sologub、Gabriele Pradel、Ulrike Holzgrabe

  DOI：10.1016/j.bmc.2010.03.067

  日期：2010.5

  The bisquaternary bisnaphthalimides are a versatile class of compounds being active against the malaria parasite Plasmodium falciparum in the lower nanomolar range of concentration combined with no cytotoxicity. The series of compounds is designed as choline analogues and interfering agents of the phosphatidylcholine biosynthesis. The qualitative analysis of the structure-activity relationships (SAR) revealed the importance of a long methylene middle chain of at least 8 methylene groups between the two bisquaternary naphthalimides or a monoquaternary naphthalimide consisting of a long alkyl chain attached to the positively charged nitrogen atom. Since the SARs are different from reported biscationic antimalarial drugs the mode of action remains to be elucidated. (c) 2010 Elsevier Ltd. All rights reserved.