4-decylamino-6-methyl-2-methylsulfanylpyrimidine | 1013113-61-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-decylamino-6-methyl-2-methylsulfanylpyrimidine
• 英文别名: 4-(n-decylamino)-6-methyl-2-(methylthio)pyrimidine；4-Decylamino-6-methyl-2-methylsulfanylpyrimidine；N-decyl-6-methyl-2-methylsulfanylpyrimidin-4-amine
• CAS: 1013113-61-5
• 化学式: C₁₆H₂₉N₃S
• 分子量: 295.492
• InChiKey: AWXHXHXZUPORCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-decylamino-6-methyl-2-methylsulfanylpyrimidine 、 对甲苯磺酸甲酯 反应 5.0h， 生成 4-decylamino-1,6-dimethyl-2-methylsulfanylpyrimidin-1-ium p-toluenesulfonate
  参考文献：
  名称：

  Study of the protonation (methylation) position and tautomeric structure of thiopyrimidine derivatives by 2D 1H—15H NMR HSQC/HMBC. Experimental approach and theoretical modeling

  摘要：

  二维 1H-15N NMR HSQC/HMBC 实验能够明确确定含氮杂环的质子化（甲基化）位置和同分异构体结构。在所研究的噻吩嘧啶中，质子化（或甲基化）发生在嘧啶环的 N（1）原子上。根据 1H-15N NMR 光谱分析，确定了这些化合物的同分异构体结构。化学位移的 Ab initio 计算（GIAO B3LYP/6-31G(d)//HF/6-31G）与实验值完全一致。热力学方法解释了各种质子化（甲基化）和同分异构体的稳定性。

  DOI：

  10.1007/s11172-009-0008-4
• 作为产物：
  描述：

  4-(n-decylamino)-6-methylpyrimidine-2-thione 、 硫酸二甲酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4-decylamino-6-methyl-2-methylsulfanylpyrimidine
  参考文献：
  名称：

  Study of the protonation (methylation) position and tautomeric structure of thiopyrimidine derivatives by 2D 1H—15H NMR HSQC/HMBC. Experimental approach and theoretical modeling

  摘要：

  二维 1H-15N NMR HSQC/HMBC 实验能够明确确定含氮杂环的质子化（甲基化）位置和同分异构体结构。在所研究的噻吩嘧啶中，质子化（或甲基化）发生在嘧啶环的 N（1）原子上。根据 1H-15N NMR 光谱分析，确定了这些化合物的同分异构体结构。化学位移的 Ab initio 计算（GIAO B3LYP/6-31G(d)//HF/6-31G）与实验值完全一致。热力学方法解释了各种质子化（甲基化）和同分异构体的稳定性。

  DOI：

  10.1007/s11172-009-0008-4

文献信息

• Pyrimidinophane p-toluenesulfonate—Water-soluble pyrimidine-containing macrocycles
  作者：V. E. Semenov、A. S. Mikhailov、E. S. Romanova、A. D. Voloshina、N. V. Kulik、S. Yu. Uraleva、A. V. Kozlov、Sh. K. Latypov、V. S. Reznik

  DOI：10.1134/s1070363209010216

  日期：2009.1

  Reactions of pyrimidinophanes containing two 6-methylthiocytosine and one 6-methyluracil fragments with methyl p-toluenesulfonate gave amphiphilic macrocyclic bis-p-toluenesulfonates. Despite the presence of several reaction centers in the initial pyrimidinophane molecules, methylation occurred only at the N-1 atom (with quaternization) of the 6-methylthiocytosine fragments. Bacteriostatic and fungistatic activity of the products was estimated.
• Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties
  作者：Vyacheslav E. Semenov、Anatoly S. Mikhailov、Alexandra D. Voloshina、Natalia V. Kulik、Alexandra D. Nikitashina、Vladimir V. Zobov、Sergey V. Kharlamov、Shamil K. Latypov、Vladimir S. Reznik

  DOI：10.1016/j.ejmech.2011.05.034

  日期：2011.9

  Reactions of pyrimidinophanes with two 6-methylthiocytosine and one 5(6)-alkyluracil moieties bridged with each other by polymethylene spacers with methyl or nonyl p-toluenesulfonate, p-toluenesulfonic acid, methanesulfonate and trifluorosulfonate afforded amphiphilic macrocyclic bis-p-toluene-, methane- and trifluorosulfonates. Despite the presence of several reaction centers in the initial pyrimidinophane molecules, protonation and methylation occurred only at the N-1 atom (with quaternization) of the 6-methylthiocytosine moieties. The bacteriostatic and fungistatic activity of the products was estimated. Macrocyclic tosylates exhibit a remarkable selectivity towards Staphylococcus aureus, with MIC values comparable with a reference drug. Bacteriostatic activity of the amphiphilic pyrimiclinophanes depends on the size of the macrocycles, and the highest activity corresponds to definite lengths of polymethylene bridges. Besides, the antimicrobial activity of the screened pyrimidine derivatives depends on their topology. While macrocyclic tosylates are more active against bacteria than against fungi, acyclic tosylate with the same structural fragments shows a dramatical decrease of MIC towards mold and yeast with respect to the corresponding macrocycle. It is found that macrocyclic and acyclic tosylates in high dilutions decrease the extracellular lipase activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Study of the protonation (methylation) position and tautomeric structure of thiopyrimidine derivatives by 2D 1H—15H NMR HSQC/HMBC. Experimental approach and theoretical modeling
  作者：A. V. Kozlov、V. E. Semenov、A. S. Mikhailov、A. V. Il’yasov、V. S. Reznik、Sh. K. Latypov

  DOI：10.1007/s11172-009-0008-4

  日期：2009.1

  Two-dimensional 1H—15N NMR HSQC/HMBC experiments enable the unambiguous determination of the protonation (methylation) position and tautomeric structure of nitrogen-containing heterocycles. In investigated thiopyrimidines protonation (or methylation) occurs at the N(1) atom of the pyrimidine ring. The tautomeric structures of these compounds were established based on the analysis of 1H—15N NMR spectra. Ab initio calculations of chemical shifts (GIAO B3LYP/6-31G(d)//HF/6-31G) are in full agreement with experimental values. The stability of various protonated (methylated) and tautomeric species is explained in terms of a thermodynamic approach.

  二维 1H-15N NMR HSQC/HMBC 实验能够明确确定含氮杂环的质子化（甲基化）位置和同分异构体结构。在所研究的噻吩嘧啶中，质子化（或甲基化）发生在嘧啶环的 N（1）原子上。根据 1H-15N NMR 光谱分析，确定了这些化合物的同分异构体结构。化学位移的 Ab initio 计算（GIAO B3LYP/6-31G(d)//HF/6-31G）与实验值完全一致。热力学方法解释了各种质子化（甲基化）和同分异构体的稳定性。