5,5,5',5'-Tetramethylperhydro-2,2'-bipyrimidine | 122763-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,5,5',5'-Tetramethylperhydro-2,2'-bipyrimidine
• 英文别名: 2,2'-bis(5,5'dimethylhexahydropyrimidine)；2-(5,5-Dimethyl-1,3-diazinan-2-yl)-5,5-dimethyl-1,3-diazinane
• CAS: 122763-14-8
• 化学式: C₁₂H₂₆N₄
• 分子量: 226.365
• InChiKey: LTJTUJXXPDGYJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5,5',5'-Tetramethylperhydro-2,2'-bipyrimidine 在 硝酸 、 三氟乙酸酐 作用下， 以9%的产率得到2,2'-bis(1,3-dinitro-5,5-dimethylhexahydropyrimidine)
  参考文献：
  名称：

  Synthesis of fused polyazapolycyclic compounds through condensation of diaminoalkanes with carbonyl compounds

  摘要：

  DOI：

  10.1021/jo00281a016
• 作为产物：
  描述：

  二甲基丙二胺 、 草酸醛 以 甲醇 为溶剂， 生成 5,5,5',5'-Tetramethylperhydro-2,2'-bipyrimidine
  参考文献：
  名称：

  1,5-二氮杂双环[3.1.0]己烷的合成、结构及构象特性

  摘要：

  首次获得了一批新的3,3-二甲基-1,5-二氮杂双环[3.1.0]己烷，并通过X射线衍射分析、光谱和物理化学方法对其进行了表征。通过量子化学方法和晶体堆积建模方法分析了所考虑化合物的对映异构体的特征。结果表明，固态的分子间相互作用从根本上改变了1,5-二氮杂双环[3.1.0]己烷的构象结构的性质。

  DOI：

  10.1016/j.molstruc.2022.133856

文献信息

• Reactions of perhydro-2,2'-bipyrimidines with carbonyl compounds bearing .alpha.-carbonyl functionality
  作者：Donald C. Craig、Alan Doughty、Michael Kassiou、Malcolm G. MacIntosh、Roger W. Read

  DOI：10.1021/jo00073a039

  日期：1993.10

  Treatment of perhydro-2,2'-bipyrimidine (1) with glyoxal, glyoxylic acid, and ethyl glyoxylate in MeOH yields 10b,10c-trans-4,5,9,10-tetramethoxyperhydro-3a,5a,8a,10a-tetraazapyrene (5), 1,3-diazacyclohexane-2-carboxylic acid (9) and 10b,10c-trans-5,10-dimethoxyperhydro-3a,5a,8a,10a-tetraazapyrene-4,9-dione (10), respectively, while similar treatment of 5,5,5',5'-tetramethylperhydro-2,2'-bipyrimidine (2) with glyoxal gives an inseparable mixture of 10b,10c-trans-4,5,9,10-tetramethoxy-2,2,7,7-tetramethylperhydro-3a,5a,8a,10a-tetraazapyrene (7) and an isomeric substance and reaction with diethyl oxomalonate gives ethyl 4a,4b-trans-9-hydroxy-10-oxoperhydro-4,5,8a,10a-tetraazaphenanthrene-9-carbox ylate (12) or an unequal mixture of diethyl 10b,10c-trans-4,9-dihydroxy-5,10-dioxoperhydro-3a,5a,8a,10a-tetraazapyrene-4,9-dicarboxylate (13) and diethyl 10b,10c-trans-4,10-dihydroxy-5,9-dioxoperhydro-3a,5a,8a,10a-tetraazapyrene-4, 10-dicarboxylate (14), respectively, depending upon reaction conditions. The relative configuration of substituents in 5 is determined by NOE difference experiments, and the structure of 10 is confirmed by X-ray crystallography. Formation of these compounds represents a departure from the mode of condensation of perhydro-2,2'-bipyrimidines with simple aldehydes and ketones.
• Synthesis of fused polyazapolycyclic compounds through condensation of diaminoalkanes with carbonyl compounds
  作者：David St. Clair Black、Donald C. Craig、Olga Giitsidis、Roger W. Read、Abdoreza Salek、Mark A. Sefton

  DOI：10.1021/jo00281a016

  日期：1989.9
• Synthesis, structure and peculiarity of conformational behavior of 1,5-diazabicyclo[3.1.0]hexanes
  作者：V.V. Kuznetsov、D.V. Khakimov、A.S. Dmitrenok、A.S. Goloveshkin

  DOI：10.1016/j.molstruc.2022.133856

  日期：2022.12

  obtained and characterized by X-ray diffraction analysis, spectral and physicochemical methods. The features of the enantiomers of the considered compounds are analysed by quantum chemistry methods and crystal packing modeling methods. It is shown that intermolecular interactions in solid state radically change the nature of the conformational structure of 1,5-diazabicyclo[3.1.0]hexanes.

  首次获得了一批新的3,3-二甲基-1,5-二氮杂双环[3.1.0]己烷，并通过X射线衍射分析、光谱和物理化学方法对其进行了表征。通过量子化学方法和晶体堆积建模方法分析了所考虑化合物的对映异构体的特征。结果表明，固态的分子间相互作用从根本上改变了1,5-二氮杂双环[3.1.0]己烷的构象结构的性质。