1,12-diaminododecane dihydrochloride | 15536-18-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,12-diaminododecane dihydrochloride
• 英文别名: diaminohexaethylene dihydrochloride；1,12-Dodecanediamine, dihydrochloride；Dodecane-1,12-diamine;hydrochloride；dodecane-1,12-diamine;hydrochloride
• CAS: 15536-18-2
• 化学式: C₁₂H₂₈N₂*2ClH
• 分子量: 273.29
• InChiKey: GAQBLOUMUHWWLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-甲氧基-2,3,4,5-四氢吡啶 、 1,12-diaminododecane dihydrochloride 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到N,N'-bis(2,3,4,5-tetrahydropyridin-6-yl)dodecane-1,12-diamine
  参考文献：
  名称：

  Potent Antimalarial Activity of 2-Aminopyridinium Salts, Amidines, and Guanidines

  摘要：

  We describe the design, synthesis, and antimalarial activity of 60 bis-tertiary amine, bis-2(1H)-imino-heterocycle, bis-amidine, and bis-guanidine series. Bis-tertiary amines with a linker from 12 to 16 methylene groups were active against the in vitro growth of Plasmodium falciparum within the 10(-6)-10(-7) M concentration range. IC50 decreased by 2 orders of magnitude for bis-2-aminopyridinium salts, bis-amidines, and bis-guanidines (27 compounds with IC50 < 10 nM). Increasing the alkyl chain length from 6 to 12 methylene groups led to increased activity, while beyond this antimalarial activity decreased. Antimalarial activities appear to be strictly related to the basicity of the cationic head with an optimal pK(a) over 12.5. Maximal activity occurs for bis-2-aminopyridinium, two C-duplicated bis-amidines, and three bis-guanidines, with IC50 values lower than 1 nM. In. comparison to similar quaternary ammonium salts, amidinium compounds have distinct structural requirements for antimalarial activity and likely additional binding opportunities on account of their hydrogen-bond-forming properties.

  DOI：

  10.1021/jm0704752
• 作为产物：
  描述：

  1,12-二氨基十二烷 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.17h， 以100%的产率得到1,12-diaminododecane dihydrochloride
  参考文献：
  名称：

  模块化磷酸化的糖尿嘧啶衍生的分子镊子，用于脂肪族二胺的有效结合。

  摘要：

  合成了基于带有四个磷酸酯基团的基于甘脲的骨架的分子镊子，该分子镊子能够结合水溶液中的有机胺。这项工作报告了通过1 H NMR滴定确定的该分子镊子和胺客体的30种配合物的Ka值。疏水腔和磷酸基团均有助于结合。由于空间冲突和库仑排斥，较松散的分子和带有负电荷基团的分子（如氨基酸中的羧酸盐）的结合较不紧密。磷酸基团与铵客体的狭窄空腔和强离子相互作用有利于脂肪族二胺的结合。这些结合特性使该系统与结构上相关的分子夹和镊子明显区分开。

  DOI：

  10.1002/chem.201902556

文献信息

• Compounds with antiparasitic activity and medicines containing same
  申请人：Vial Henri

  公开号：US20050176819A1

  公开（公告）日：2005-08-11

  The invention relates to compounds having an anti-parasitic, in particular antimalarial activity, characterized in that they correspond to general formula (I) Applications in particular as compounds with anti-parasitic activity.

  这项发明涉及具有抗寄生虫特别是抗疟活性的化合物，其特征在于它们符合一般式(I)。特别适用于具有抗寄生虫活性的化合物。
• Allosteric Binding‐Induced Intramolecular Mechanical‐Strain Engineering
  作者：Wenxian Ma、Tingting Cheng、Fang‐Zi Liu、Yan Liu、KaKing Yan

  DOI：10.1002/anie.202202213

  日期：2022.4.25

  Analogous to allosteric enzymes, guest binding introduces a directional pulling or pushing force that acts on the reverse side of a Zn salen complex. This tunable intramolecular force promotes various degrees of conformational and torsional strain, as predicted by both classical conformational analysis and DFT. This strain energy can be further applied to cleave chemical bonds, and the efficiency can

  与变构酶类似，客体结合引入了作用于 Zn salen 复合物反面的定向拉力或推力。正如经典构象分析和 DFT 所预测的，这种可调节的分子内力促进了不同程度的构象和扭转应变。这种应变能可以进一步应用于切割化学键，并且可以通过变构客体的身份来调整效率。
• Tuning the aggregation of an amphiphilic anionic calix[5]arene by selective host–guest interactions with bola-type dications
  作者：Ilenia Pisagatti、Lucia Barbera、Giuseppe Gattuso、Valentina Villari、Norberto Micali、Enza Fazio、Fortunato Neri、Melchiorre F. Parisi、Anna Notti

  DOI：10.1039/c9nj01198f

  日期：——

  species. The stoichiometry of the calixarene/diammonium ion inclusion complexes was found to be strongly dependent on the length and the number of equivalents of the guest used. The selective formation of endo-cavity “supramolecular bola-amphiphiles” and the additional interplay of electrostatic/hydrophobic interactions yielded “NMR-visible” and “NMR-invisible” supramolecular assemblies of different natures

  在稀释的溶液中观察到（低于CMC）的两亲性的纳米超分子组装对叔-butylcalix [5]芳烃五ö -butylsulfonato 1和的混合物1和不同长度的硼酸型α，ω-烷二基二铵离子。SEM分析和光散射实验表明，这些药物能够调节所研究胶体系统的大小和表面电荷。与NMR数据的比较揭示了宿主/客体识别事件的性质，揭示了超两亲性表面活性剂物种的形成。发现杯芳烃/二铵离子包合物的化学计量强烈地取决于所用客体的长度和当量数。内膜的选择性形成腔“超分子两亲”和静电/疏水相互作用的额外相互作用产生了不同性质的“ NMR可见”和“ NMR不可见”的超分子组装体。通过显着增加抗癌药他莫昔芬在水中的溶解度（> 1000倍），可以发现衍生自1和十六烷二基二铵离子的超分子bola-两亲物可作为有前途的增溶剂。
• Unconventional U-shaped conformation of a bolaamphiphile embedded in a synthetic host
  作者：Kangkyun Baek、Youngkook Kim、Hyunuk Kim、Minyoung Yoon、Ilha Hwang、Young Ho Ko、Kimoon Kim

  DOI：10.1039/c0cc00752h

  日期：——

  The X-ray crystal structure of 1,12-dodecane diammonium (C12DA2+) encapsulated in cucurbit[8]uril reveals an unconventional U-shaped conformation of C12DA2+, which is attributed to the favorable host–guest interactions to overcome the charge–charge repulsion of the two ammonium groups in close proximity and high internal strain.

  封装在葫芦[8]脲中的 1,12-十二烷二铵（C12DA2+）的 X 射线晶体结构显示，C12DA2+ 呈非常规的 U 形构象，这归因于有利的主客体相互作用，克服了两个铵基靠近时的电荷排斥和高内应变。
• Non-ionic [2]rotaxanes containing methylated α-cyclodextrins
  作者：Akira Harada、Jun Li、Mikiharu Kamachi

  DOI：10.1039/a702498c

  日期：——

  Non-ionic [2]rotaxanes have been prepared from complexes of oligoethylene derivatives with methylated α-cyclodextrins by capping them with trinitrophenyl groups as stoppers.

  非离子型 [2]rotaxanes 是由低聚乙烯衍生物与甲基化 δ-环糊精的复合物制备而成，其方法是以三硝基苯基团作为封端。