4-碘-5-硝基-1H-咪唑 | 76529-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-碘-5-硝基-1H-咪唑
• 英文名称: (4,5)-iodonitroimidazole
• 英文别名: 5-iodo-4-nitroimidazol；5-iodo-4-nitro-1H-imidazole；4-iodo-5-nitro-1H-imidazole
• CAS: 76529-48-1
• 化学式: C₃H₂IN₃O₂
• 分子量: 238.972
• InChiKey: CHZYQLYIYFQCKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-碘-5-硝基-1H-咪唑 在 氢溴酸 作用下， 反应 0.33h， 以81%的产率得到5-溴-4-硝基咪唑
  参考文献：
  名称：

  Reassignment of the structures of iodonitroimidazole, its N-methyl derivatives, and related compounds

  摘要：

  DOI：

  10.1021/jo00322a005
• 作为产物：
  描述：

  4,5-二硝基咪唑 生成 4-碘-5-硝基-1H-咪唑
  参考文献：
  名称：

  SHARNIN G. P.; FASSAXOV R. X.; ENEJKINA T. A., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO

  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。
• Nucleophilic Displacements of Imidazoles. II. Displacements of Halogen by S-Nucleophiles and Displacements of Mesyl Groups Activated by Nitro; Oxidation of Imidazolethiols
  作者：S Kulkarni、MR Grimmett

  DOI：10.1071/ch9871415

  日期：——

  In basic medium arylthiols displace bromo and iodo groups activated by nitro substituents in 5(4)-halo-4(5)- nitroimidazoles . The bromo compounds are slightly more reactive than the iodo analogues. Substituents at C5 are more readily displaced than those at C4. Methylsulfonyl groups, similarly activated by an adjacent nitro substituent, are displaced by a variety of nucleophiles. The imidazolethiol products are readily oxidized to the sulfones.

  在碱性介质中，芳基硫醇取代了 5(4)- 卤-4(5)- 硝基咪唑中由硝基取代基活化的溴基和碘基。溴代化合物的活性略高于碘代类似物。位于 C5 的取代基比位于 C4 的取代基更容易被取代。甲基磺酰基也同样被邻近的硝基取代基激活，并被各种亲核剂置换。咪唑硫醇产物很容易被氧化成砜。
• A short route to functionalized imidazo[4,5- c ]carbazoles. Synthesis of the first example of the imidazo[4,5- c ]β-carboline ring system
  作者：Said Achab、Khalid Diker、Pierre Potier

  DOI：10.1016/s0040-4039(01)01915-3

  日期：2001.12

  A new synthetic route to functionalized imidazo[4,5-c]carbazoles (4) via intramolecular electrocyclization of indolo-1,3,5-hexatriene system (3a) is described. Thermally induced ring-closure of 2-ethylcarboxylate-(4-amino-5-imidazolyl)-3-indole (3d) led to the previously unknown imidazo[4,5-c]β-carboline ring system (5). These heterocycles were efficiently converted into analogs of both the marine

  描述了一种通过吲哚-1,3,5-己三烯体系（3a）的分子内电环化合成功能化咪唑并[4,5- c ]咔唑（4）的新途径。热诱导的2-乙基羧酸酯-（4-氨基-5-咪唑基）-3-吲哚的闭环（3d）导致了以前未知的咪唑并[4,5 - c ]β-咔啉环系统（5）。这些杂环被有效地转化为海洋细胞毒性剂Grossularines-1和-2（1）和抗菌生物碱eudistomin U（2）的类似物。
• Potential radiosensitizing agents. 7. 4(5)-Iodo-5(4)-nitroimidazole derivatives
  作者：Rajender P. Gupta、Cynthia A. Larroquette、Krishna C. Agrawal、J. Grodkowski、P. Neta

  DOI：10.1021/jm00146a003

  日期：1985.8

  A series of 4(5)-iodo-5(4)-nitro-1-substituted-imidazoles has been synthesized and tested for their ability to selectively radiosensitize hypoxic Chinese hamster cells (V-79) to the lethal effect of radiation. The reaction of 4(5)-iodo-5-(4)-nitroimidazole with 1,2-epoxy-3-methoxypropane and ethyl alpha-chloroacetate produced two isomeric products in each case, which were identified by their NMR spectra. The ethyl esters were further reacted with 3-picolylamine to produce corresponding amides. The 5-iodo-4-nitroimidazole-1-N-(3-picolyl)acetamide on further reaction with m-chloroperbenzoic acid produced the corresponding N-oxide. These compounds were generally more toxic to V-79 cells than the 2-nitroimidazole derivatives and were found to be more effective radiosensitizers in vitro. The 5-iodo-4-nitroimidazole derivatives were more efficient as sensitizers than the 4-iodo-5-nitroimidazole derivatives, and the sensitizing efficiency of this class of agents was found to have significant correlation with their partition coefficients.
• Benson, Timothy J.; Robinson, Brian, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 211 - 214
  作者：Benson, Timothy J.、Robinson, Brian

  DOI：——

  日期：——