N,N'-bis(2-pyrimidyl)-1,3-trimethylenediamine | 872601-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N,N'-bis(2-pyrimidyl)-1,3-trimethylenediamine
• 英文别名: N,N'-di(2-pyrimidinyl)propane-1,3-diamine；N,N'-di(pyrimidin-2-yl)propane-1,3-diamine
• CAS: 872601-34-8
• 化学式: C₁₁H₁₄N₆
• 分子量: 230.272
• InChiKey: OYZMSTNKXRTBMH-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  462.1±55.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-pyrimidyl)-1,3-trimethylenediamine 在 polyphosphoric acid 作用下， 以 乙腈 为溶剂， 反应 5.25h， 生成 C₂₇H₂₂Cl₂N₆⁽²⁺⁾*2ClO₄^(1-)
  参考文献：
  名称：

  Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation

  摘要：

  The increased tolerance of biofilms against disinfectants and antibiotics has stimulated research into new methods of biofilm prevention and eradication. In our previous work, we have identified the 5-aryl-2-aminoimidazole core as a scaffold that demonstrates preventive activity against biofilm formation of a broad range of bacterial and fungal species. Inspired by the dimeric nature of natural 2-aminoimidazoles of the oroidin family, we investigated the potential of dimers of our decorated 5-aryl-2-aminoimidazoles as biofilm inhibitors. A synthetic approach towards 2-aminoimidazole dimers linked by an alkyl chain was developed and a total of 48 dimers were synthesized. The linkers were introduced at two different positions, the N1-position or the N2-position, and the linker length and the substitution of the 5-phenyl ring (H, F, Cl, Br) were varied. Although, no clear correlation between linker length and biofilm inhibition was observed, a strong increase in anti-biofilm activity for almost all N1, N1'-linked dimers was obtained, compared to the respective monomers against Salmonella Typhimurium, Escherichia coli and Staphylococcus aureus. The N2, N2'-linked dimers, having a H-or F-substitution, were also found to show a strong increase in anti-biofilm activity compared to the respective monomers against these three bacterial species and against Pseudomonas aeruginosa. In addition, the obtained growth measurements suggest a broad concentration range with specific biofilm inhibition and no effect on the planktonic growth against Salmonella Typhimurium and Pseudomonas aeruginosa. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2018.01.005
• 作为产物：
  描述：

  2-氯嘧啶 、 1,3-丙二胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以60%的产率得到N,N'-bis(2-pyrimidyl)-1,3-trimethylenediamine
  参考文献：
  名称：

  Ag(i) complexes with alkylidene-bis(2-aminopyrimidines) as building units for discrete metallomacrocyclic frames. A structural and solution study

  摘要：

  烯叉双(2-氨基嘧啶)(pyr2Cx, x = 2–5)是有用的配体，能与Ag(I)生成离散的金属环。分离得到了[(pyr2C2)Ag(NO3)]2和[(H-pyr2C4)Ag(NO3)2]2的晶体结构，其中每个大环部分都通过弱相互作用与其周围环境相互作用，形成三维离散结构。另一方面，溶液研究显示，Ag(pyr2Cx)+配合物的形成平衡常数高于已知文献中单嘧啶Ag(I)配合物的值，尽管这种差异可以通过考虑Ag(I)-pyr2Cx配合物的固态结构来解释。

  DOI：

  10.1039/b508260a

文献信息

• Metallomacrocycles as anion receptors: combining hydrogen bonding and ion pair based hosts formed from Ag(i) salts and flexible bis- and tris-pyrimidine ligands
  作者：Andres Tasada、Francisca M. Albertí、Antonio Bauzá、Miquel Barceló-Oliver、Angel García-Raso、Juan J. Fiol、Elies Molins、Amparo Caubet、Antonio Frontera

  DOI：10.1039/c3cc40772a

  日期：——

  Two self-assembled hosts are formed from Ag(I) salts and bis-pyrimidyl ligands and X-ray characterized. Both are able to incorporate two anions into the structure combining hydrogen bonding and electrostatic interactions.

  由 Ag（I）盐和双嘧啶配体形成的两种自组装宿主具有 X 射线特征。两者都能通过氢键和静电相互作用将两个阴离子结合到结构中。
• Amination of 2-chloro-and 2,4-dichloropyrimidines by polyamines
  作者：A. D. Averin、O. A. Ulanovskaya、I. P. Beletskaya

  DOI：10.1007/s10593-008-0165-7

  日期：2008.9

  A study was carried out on the amination of 2-chloro-and 2,4-dichloropyrimidines by linear polyamines and oxadiamines under catalytic and noncatalytic conditions. The reaction of excess polyamine with 2-chloropyrimidine gives the corresponding 2-aminopyrimidines, while the reaction of polyamines with excess of 2-chloropyrimidine gives di-, tri-, and tetraarylated derivatives. The reaction of 2,4-dichloropyrimidine with diamines was studied with different ratios of the starting reagents. The ratios of the products of substitution at pyrimidine C-2 and C-4 were found.