N,N,N'-trimethylhexanediamide | 1862-10-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N,N'-trimethylhexanediamide
• 英文别名: N,N,N'-Trimethyladipamid；N~1~,N~1~,N~6~-Trimethylhexanediamide；N,N',N'-trimethylhexanediamide
• CAS: 1862-10-8
• 化学式: C₉H₁₈N₂O₂
• 分子量: 186.254
• InChiKey: VCVONRGXZKRDAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N,N'-trimethylhexanediamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N,N,N',N",N"-pentamethyldixyylenetriamine
  参考文献：
  名称：

  神经肌肉阻滞剂：简单线性三元化合物的烷基和杂环类似物。

  摘要：

  进一步合成了一系列线性六亚甲基-NNN-三季铵化合物，并测试了其神经肌肉阻滞活性。在烷基取代衍生物中，至少需要一个乙基才能在哺乳动物中表现出显著的效力。除了Et2Bun和EtBu2n化合物外，较大的烷基取代基会降低效力。在哺乳动物中高效力需要至少在末端氮上有两个乙基基团，如果第三个基团不是甲基。吗啡啶衍生物只表现出弱活性，但家禽对哌啶和四氢吗啡啶化合物非常敏感。讨论了结果。

  DOI：

  10.1111/j.2042-7158.1964.tb07544.x
• 作为产物：
  描述：

  N,N-dimethyl-adipamic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 N,N,N'-trimethylhexanediamide
  参考文献：
  名称：

  神经肌肉阻滞剂：简单线性三元化合物的烷基和杂环类似物。

  摘要：

  进一步合成了一系列线性六亚甲基-NNN-三季铵化合物，并测试了其神经肌肉阻滞活性。在烷基取代衍生物中，至少需要一个乙基才能在哺乳动物中表现出显著的效力。除了Et2Bun和EtBu2n化合物外，较大的烷基取代基会降低效力。在哺乳动物中高效力需要至少在末端氮上有两个乙基基团，如果第三个基团不是甲基。吗啡啶衍生物只表现出弱活性，但家禽对哌啶和四氢吗啡啶化合物非常敏感。讨论了结果。

  DOI：

  10.1111/j.2042-7158.1964.tb07544.x

文献信息

• Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: variable-temperature NMR and IR studies on a homologous diamide series
  作者：Samuel H. Gellman、Gregory P. Dado、Gui Bai Liang、Bruce R. Adams

  DOI：10.1021/ja00004a016

  日期：1991.2

  We have studied intramolecular hydrogen bonding in a homologous series of diamides (compounds 1-6) in methylene chloride, 9:1 carbon tetrachloride/benzene, and acetonitrile. By correlating variable-temperature H-1 NMR and IR measurements, we have shown that the temperature dependence of the amide proton NMR chemical shift (DELTA-delta/DELTA-T) can provide qualitative (and in some cases quantitative) information on the thermodynamic relationship between the intramolecularly hydrogen bonded and non-hydrogen-bonded states of flexible molecules. Among the hydrogen-bonded ring sizes represented in the diamide series, the intramolecular interaction is particularly enthalpically favorable in the nine-membered hydrogen-bonded ring (compound 4). Variable-temperature IR and NMR data indicate that the internally hydrogen bonded state of diamide 4 is 1.4-1.6 kcal/mol more favorable enthalpically than the non-hydrogen-bonded state, in methylene chloride solution; the non-hydrogen-bonded state is 6.8-8.3 eu more favorable entropically in this solvent. In contrast, there appear to be much smaller enthalpy differences between the internally hydrogen bonded and non-hydrogen-bonded states of diamides 2 and 3. Our findings are important methodologically because the temperature dependences of amide proton chemical shifts are commonly used to elucidate peptide conformation in solution. Our results show that previous "rules" for the interpretation of such data are incomplete. In non-hydrogen-bonding solvents, small amide proton DELTA-delta/DELTA-T values have been taken to mean that the proton is either entirely free of hydrogen bonding or completely locked in an intramolecular hydrogen bond over the temperature range studied. We demonstrate that an amide proton can be equilibrating between intramolecularly hydrogen bonded and non-hydrogen-bonded states and still manifest a small chemical shift temperature dependence (implying that the hydrogen-bonded and non-hydrogen-bonded states are of similar enthalpy).
• Process for Preparing Esteramide Compounds
  申请人：Vidal Thierry

  公开号：US20130237722A1

  公开（公告）日：2013-09-12

  The present invention relates to a method for preparing esteramide compounds. More particularly, the invention relates to a method for preparing esteramide compounds by reaction between a diester and an amine, in the presence of a basic compound, wherein the amine is solubilized in an organic solvent or in the diester, when the amine is solubilized in an organic solvent, the diester is added onto the reaction mixture comprising the amine and the basic compound, when the amine is solubilized in the diester, the basic compound is added onto the reaction mixture comprising the amine and the diester (II), the reaction is conducted at a temperature greater than or equal to 30° C., the amine is present in molar excess ranging from 0.01 to 50% relatively to the diester.
• US9284262B2
  申请人：——

  公开号：US9284262B2

  公开（公告）日：2016-03-15
• Neuromuscular blocking agents: alkyl and heterocyclic analogues of simple linear trisonium compounds
  作者：Fiona MacLeod Carey、C I Furst、J J Lewis、J B Stenlake

  DOI：10.1111/j.2042-7158.1964.tb07544.x

  日期：2011.4.12

  A further series of linear hexamethylene-NNN-trisonium compounds has been synthesised and tested for neuromuscular blocking activity. In the alkyl-substituted derivatives, at least one Et is required for significant potency in mammals. Apart from the Et2Bun and EtBu2n compounds, larger alkyl substituents lower potency. High potency in mammals requires at least two Et groups on the terminal nitrogens, if the third group is not Me. Only weak activity was shown by the morpholino-deriatives but the fowl was highly sensitive towards the piperidino- and tetrahydro-papaverino-compounds. The results are discussed.

  进一步合成了一系列线性六亚甲基-NNN-三季铵化合物，并测试了其神经肌肉阻滞活性。在烷基取代衍生物中，至少需要一个乙基才能在哺乳动物中表现出显著的效力。除了Et2Bun和EtBu2n化合物外，较大的烷基取代基会降低效力。在哺乳动物中高效力需要至少在末端氮上有两个乙基基团，如果第三个基团不是甲基。吗啡啶衍生物只表现出弱活性，但家禽对哌啶和四氢吗啡啶化合物非常敏感。讨论了结果。