N,N,N,N',N',N'-hexamethyldodecane-1,12-diammonium dibromide | 1674-82-4

• 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'-hexamethyldodecane-1,12-diammonium dibromide
• 英文别名: hexa-N-methyl-N,N'-dodecanediyl-di-ammonium; dibromide；Hexa-N-methyl-N,N'-dodecandiyl-di-ammonium; Dibromid；1,12-bis-(trimethylammonium)dodecane dibromide
• CAS: 1674-82-4
• 化学式: 2Br*C₁₈H₄₂N₂
• 分子量: 446.353
• InChiKey: CEGKRZMHCRHTMV-UHFFFAOYSA-M

物化性质

• 熔点：
  190-191 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21.0
• 可旋转键数：
  13.0
• 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'-hexamethyldodecane-1,12-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'-hexamethyldodecane-1,12-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

• Interaction of Bolaform Surfactants with <i>p</i>-Sulfonatocalix[4]Arene: The Role of Two Positive Charges in the Binding
  作者：Vitor Francisco、Luis Garcia-Rio

  DOI：10.1021/la501337c

  日期：2014.6.17

  The inclusion binding manners of bolaform surfactants of type CnR62+ 2Br– with different spacer lengths (n = 6, 12) and terminal headgroup volumes (R = methyl, ethyl) by p-sulfonatocalix[4]arene were studied. The combination of ITC parameters (binding constants and complexation enthalpy and entropy) and NMR chemical shifts and NOE cross-peaks obtained upon complexation allows us to propose different

  夹杂物结合C类的Bola型表面活性剂的方式ñ - [R 6 2+ 2BR -用不同的间隔基长度（Ñ = 6，12）和终端首基卷（R =甲基，乙基）由p研究了-sulfonatocalix [4]芳烃。ITC参数（结合常数以及络合焓和熵）和NMR化学位移以及在络合后获得的NOE交叉峰的组合使我们能够提出不同的结合模式。结果指出，间隔物的长度对结合化学计量有影响。在极性头基团之间具有较大间隔区长度的呈链状形式，除了可以形成1：1以外，还可以形成2：1的复合物，而对于较短间隔区，它们只能形成1：1的复合物。另一方面，1：1络合物的形成不受头状体的体积或杯状间隔物长度的影响。出乎意料的是，观察到复杂的结合模式，其中杯状体的两个带正电的末端基团都容纳在杯芳烃的腔中。
• [EN] BIS-CATIONIC COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSES BIS-CATIONIQUES ET UTILISATION ASSOCIEE
  申请人：UNIV SYDNEY

  公开号：WO2005047230A1

  公开（公告）日：2005-05-26

  The present invention relates to bis-cationic compounds comprising quaternary ammonium groups and/or quaternary phosphonium groups. The invention also relates to the use of bis-cationic compounds as Phospholipase B inhibitors and the use of bis­ cationic compounds for the treatment or prevention of microbial infection.

  本发明涉及含有季铵基团和/或四元磷基团的双阳离子化合物。该发明还涉及将双阳离子化合物用作磷脂酶B抑制剂以及将双阳离子化合物用于治疗或预防微生物感染。
• Porous Gold Nanobelts Templated by Metal−Surfactant Complex Nanobelts
  作者：Lianshan Li、Zhijian Wang、Teng Huang、Jinglin Xie、Limin Qi

  DOI：10.1021/la1015737

  日期：2010.7.20

  nanobelts formed by a bolaform surfactant dodecane-1,12-bis(trimethylammonium bromide) (N-C12-NBr2) and HAuCl4. It was revealed that the precursor nanobelts of the stoichiometric N-C12-N(AuCl4)2 complex formed through electrostatic combination of the positively charged quaternary ammonium headgroups of N-Cn-NBr2 and the negatively charged AuCl4− ions. They were subsequently converted into porous gold nanobelts

  通过形态保留的转化，从由硼酸盐表面活性剂十二烷-1,12-双（三甲基溴化铵）（NC 12 -NBr ）形成的金属表面活性剂复合物前体纳米带上进行形态保留的转化，以高收率合成了由自组织纳米颗粒组成的独特的多孔金纳米带。2）和HAuCl 4。据透露，化学计量NC的前体纳米带12 -N（AUCL 4）2配合物通过NC的带正电荷的季铵首基静电结合形成Ñ -NBr 2和带负电荷的AUCL 4 -离子。经NaBH 4还原后，它们随后被转化为尺寸缩小的多孔金纳米带。可以通过改变反应溶液中NC 12 -NBr 2和HAuCl 4的混合比例来调节所产生的金纳米结构的形态。发现与固体金纳米带相比，所获得的多孔Au纳米带对4-硝基苯酚的还原表现出增强的催化活性，这可能是由于其更大的表面积和更多的活性位点。
• 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.
• Barlow; Ing, 1948, vol. 3, p. 303
  作者：Barlow、Ing

  DOI：——

  日期：——