1,8-Octanediaminium, N,N,N,N',N',N'-hexamethyl-, dibromide | 52780-76-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,8-Octanediaminium, N,N,N,N',N',N'-hexamethyl-, dibromide
• 英文别名: 1,8-bis(trimethylammonium)octane dibromide；hexa-N-methyl-N,N'-octanediyl-di-ammonium; dibromide；Hexa-N-methyl-N,N'-octandiyl-di-ammonium; Dibromid
• CAS: 52780-76-4
• 化学式: 2Br*C₁₄H₃₄N₂
• 分子量: 390.245
• InChiKey: GOVNIOJTGYOCTL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 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：

  1,8-Octanediaminium, N,N,N,N',N',N'-hexamethyl-, 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 1,8-Octanediaminium, N,N,N,N',N',N'-hexamethyl-, 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

• 一种双季铵盐类化合物的制备方法
  申请人：大连理工大学

  公开号：CN113004149A

  公开（公告）日：2021-06-22

  本发明属于化学领域，提供一种双季铵盐类化合物的制备方法。所述制备方法以二溴烷烃和三甲胺水溶液为原料，采用乙醇为溶剂，使反应在均相体系中反应，在25～80℃反应4‑48小时，反应结束后通过蒸馏和洗涤处理得到纯品。本发明反应简单、高效、成本低，制备过程中能够避免使用三甲胺气体等安全风险高的原料和三甲胺甲醇溶液等经济成本高的原料；克服单独使用三甲胺水溶液和二溴烷烃为反应原料时导致的非均相反应和转化率低的缺点；后处理过程不使用乙醚等高危有机溶剂，所有使用的有机溶剂均可回收。
• Barlow; Ing, British Journal of Pharmacology and Chemotherapy, 1948, vol. 3, p. 300
  作者：Barlow、Ing

  DOI：——

  日期：——