1-methyl-5-nitro-4-piperidinoimidazole | 113121-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-5-nitro-4-piperidinoimidazole
• 英文别名: 1-(1-methyl-5-nitro-1H-imidazol-4-yl)-piperidine；1-Methyl-5-nitro-4-(1-piperidino)imidazol；4-Nitro-5-piperidino-1-methylimidazol；1-(1-Methyl-5-nitroimidazol-4-yl)piperidine
• CAS: 113121-68-9
• 化学式: C₉H₁₄N₄O₂
• 分子量: 210.236
• InChiKey: TWKILPPPVBIHOH-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±30.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-methyl-4-methylsulfonyl-5-nitroimidazole 、 哌啶 以67%的产率得到
  参考文献：
  名称：

  KULKARNI, SURENDRA;GRIMMETT, M. ROSS, AUSTRAL. J. CHEM., 40,(1987) N 8, 1415-1425

  摘要：

  DOI：

文献信息

• Nucleophilic Displacements of Imidazoles. I. Oxygen, Nitrogen and Carbon Nucleophiles
  作者：S Kulkarni、MR Grimmett、LR Hanton、J Simpson

  DOI：10.1071/ch9871399

  日期：——

  4(5)- Bromo - and - iodo-imidazoles, activated by an adjacent nitro substituent, undergo nucleophilic displacement with methoxide, phenoxide , cyclic secondary chines and cyanide. The regiochemistry of the reactions of 5-iodo-4-nitroimidazole with methoxide has been confirmed by spectroscopic and X-ray methods, and a number of erroneous structures from the literature have been revised. Some apparently anomalous reactions of methoxide with 5-halo-1,2-dimethyl-4- nitroimidazoles, and of cyanide with 4-halo-1-methyl-5-nitroimidazole have been noted. The crystal and molecular structure of 5-methoxy-1-methyl-4-nitroimidazole has been determine: by direct methods. Crystals are monoclinic, P21/c, a 10.929(3), b 8 899(2), c 7.290(2) �; β 92.87(2)�; Z 4. The structure was refined to R = 0.095 for 818 reflections (I > 2σI).

  4(5)-溴-和-碘-咪唑在邻近硝基取代基的活化下，与甲醇、苯酚、环仲胺和氰化物发生亲核置换反应。光谱和 X 射线方法证实了 5-碘-4-硝基咪唑与甲醇反应的区域化学性质，并修正了文献中一些错误的结构。还注意到甲醇与 5-卤代-1,2-二甲基-4-硝基咪唑以及氰化物与 4-卤代-1-甲基-5-硝基咪唑的一些明显异常反应。通过直接方法确定了 5-甲氧基-1-甲基-4-硝基咪唑的晶体和分子结构。晶体为单斜晶系，P21/c，a 10.929(3)，b 8 899(2)，c 7.290(2) �；β 92.87(2)�；Z 4。818 个反射（I > 2σI）的结构精制为 R = 0.095。
• Regioselective Nitro Group Substitution. Synthesis of Isomeric 4-Amino-5-nitro- and 5-Amino-4-nitroimidazoles
  作者：Lucjusz Zaprutko、Justyna Żwawiak、Dorota Olender、Andrzej Gzella

  DOI：10.3987/com-12-12502

  日期：——

  On the basis of the reactions between 4,5-dinitroimidazole derivatives (1-methyl-4,5-dinitroimidazole, 1,2-dimethyl-4,5-dinitroimidazole and ethyl 2-(4,5-dinitroimidazol-1-yl)acetate) and cyclic amines (morpholine, piperidine or pyrrolidine) in mild conditions (THF or ethanolic solution), the order of nitro group substitution has been discovered for the first time. The influence of the solvent, steric effects and possibility of hydrogen bonds formation on the reaction direction has been discussed. Also, the way of formation of diamino-substitution product and interesting isomerization process is presented.
• KULKARNI, SURENDRA;GRIMMETT, M. ROSS;HANTON, LYALL R.;SIMPSON, JIM, AUSTRAL. J. CHEM., 40,(1987) N 8, 1399-1413
  作者：KULKARNI, SURENDRA、GRIMMETT, M. ROSS、HANTON, LYALL R.、SIMPSON, JIM

  DOI：——

  日期：——
• KULKARNI, SURENDRA;GRIMMETT, M. ROSS, AUSTRAL. J. CHEM., 40,(1987) N 8, 1415-1425
  作者：KULKARNI, SURENDRA、GRIMMETT, M. ROSS

  DOI：——

  日期：——