1-morpholino-2,4,6-trinitrobenzene | 77379-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1-morpholino-2,4,6-trinitrobenzene
• 英文别名: 2,4,6-trinitro-1-morpholinobenzene；4-picryl-morpholine；4-Picryl-morpholin；4-(2,4,6-Trinitrophenyl)morpholine
• CAS: 77379-03-4
• 化学式: C₁₀H₁₀N₄O₇
• mdl: MFCD00088496
• 分子量: 298.212
• InChiKey: CPZXPDQTMDRNBY-UHFFFAOYSA-N

物化性质

• 熔点：
  166-166.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  475.4±45.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-morpholino-2,4,6-trinitrobenzene 在 sodium hydroxide 、 sodium chloride 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,4,6-三硝基苯酚阴离子
  参考文献：
  名称：

  Bujan, Elba I.; Remedi, M. Virginia; De Rossi, Rita H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 5, p. 969 - 975

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 、 sodium chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 1-morpholino-2,4,6-trinitrobenzene
  参考文献：
  名称：

  Bujan, Elba I.; Remedi, M. Virginia; De Rossi, Rita H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 5, p. 969 - 975

  摘要：

  DOI：

文献信息

• Hydrogen Bond Contribution to Preferential Solvation in S_NAr Reactions
  作者：Rodrigo Ormazabal-Toledo、José G. Santos、Paulina Ríos、Enrique A. Castro、Paola R. Campodónico、Renato Contreras

  DOI：10.1021/jp4005295

  日期：2013.5.16

  Preferential solvation in aromatic nucleophilic substitution reactions is discussed using a kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of secondary alicyclic amines toward phenyl 2,4,6-trinitrophenyl ether in aqueous ethanol mixtures of different compositions. From solvent effect studies, it is found that only piperidine is sensitive

  芳香族亲核取代反应中的优先溶剂化是通过动力学研究与量子化学计算相辅相成的。该模型系统是一系列仲脂环族胺在不同组成的含水乙醇混合物中对苯基2,4,6-三硝基苯基醚的反应。从溶剂作用研究中发现，只有哌啶对溶剂化作用敏感，其结果可以追溯到乙醇/水混合物中溶剂组合物的极性，这表明在水相中有特定的亲电溶剂化作用。
• Banjoko, Olayinka; Khalil-Ur-Rahman, Journal of the Chemical Society. Perkin transactions II, 1981, p. 1105 - 1108
  作者：Banjoko, Olayinka、Khalil-Ur-Rahman

  DOI：——

  日期：——
• New Compounds. Miscellaneous Derivatives of Morpholine
  作者：Ronald Henry、William Dehn

  DOI：10.1021/ja01162a601

  日期：1950.6
• Nucleophilic reactivity: nucleophilic aromatic substitution reactions of 2,4-dinitrochlorobenzene and picryl chloride in aqueous and methanol solutions
  作者：Joseph R. Gandler、Irianto U. Setiarahardjo、Chrisanthus Tufon、Chinpan Chen

  DOI：10.1021/jo00041a021

  日期：1992.7

  Rate constants for nucleophilic aromatic substitution reactions of picryl chloride, I, with acetate ion and a series of amine nucleophiles, including primary, secondary, tertiary (quinuclidines), and amines which show the alpha-effect, in aqueous and methanol solutions have been measured. Rate constants have also been measured, in water, for the reactions of 2,4-dinitrochlorobenzene, II, with trifluoroethylamine and semicarbazide. Reactions of picryl chloride with 3-quinuclidinol and DABCO yield picrate ion via general base catalyzed hydrolysis. On the other hand, reaction with quinuclidine proceeds at least in part via a mechanism in which N-picrylquinuclidinium ion is formed and then converted into a N-picrylpiperidine derivative. When the kinetic data are combined with data previously reported in the literature, the slopes of plots of log of the second-order rate constants against Ritchie's N+ parameter are 0.95 +/- 0.13 and 0.79 +/- 0.11 for the reactions of 2,4-dinitrochlorobenzene and picryl chloride, respectively (the reported error limits are the 95% confidence intervals). Steric effects may be important in these reactions, but these effects do not significantly change the slopes of the N+ correlation lines. The slope smaller than one for the reactions of picryl chloride is consistent with decreased selectivity towards nucleophilic attack, and with the modified form of Ritchie's equation, log k = S+N+ + log k0, in which relative nucleophilic reactivities are substrate dependent.
• Kinetic and equilibrium studies of ?-adduct formation and nucleophilic substitution in the reactions of morpholine with 1,3,5-trinitrobenzene and some phenyl aryl ethers in dimethyl sulphoxide
  作者：Rachel A. Chamberlin、Michael R. Crampton、Ian A. Robotham

  DOI：10.1002/(sici)1099-1395(199603)9:3<152::aid-poc769>3.0.co;2-4

  日期：1996.3

  Reactions of morpholine in dimethyl sulphoxide at unsubstituted ring positions of 1,3,5-trinitrobenzene, and phenyl 2,4,6-trinitrophenyl ether, yield anionic sigma-adducts via zwitterionic intermediates. Reactions at the 1-position of phenyl 2,4,6-trinitrophenyl ether, phenyl 2,4-dinitronaphthyl ether, and phenyl 2,4-dinitrophenyl ether result in substitution of the phenoxy groups. In both these reaction types proton-transfer is rate-limiting. Comparison of kinetic and equilibrium data with those for corresponding reactions of piperidine shows that rate constants for proton transfer are similar for the two amines, but equilibrium constants for zwitterion formation have lower values for morpholine, the less basic amine. Implications for base catalysis are discussed.