4-碘-1-甲基-5-硝基咪唑 | 76529-47-0

• 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-1-甲基-5-硝基咪唑
• 英文名称: 4-Iodo-1-methyl-5-nitroimidazole
• 英文别名: 4-iodo-1-methyl-5-nitro-1H-imidazole；1-Methyl-4-jod-5-nitroimidazol；4-Iodo-1-methyl-5-nitro-1H-imidazole
• CAS: 76529-47-0
• 化学式: C₄H₄IN₃O₂
• 分子量: 252.999
• InChiKey: HYIXYWKRGGDKJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  氰化钾 、 4-碘-1-甲基-5-硝基咪唑 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以63%的产率得到1-甲基-4-硝基-1H-咪唑-5-甲腈
  参考文献：
  名称：

  Nucleophilic Displacements of Imidazoles. I. Oxygen, Nitrogen and Carbon Nucleophiles

  摘要：

  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。

  DOI：

  10.1071/ch9871399
• 作为产物：
  描述：

  4-碘-5-硝基-1H-咪唑 、 硫酸二甲酯 生成 4-碘-1-甲基-5-硝基咪唑
  参考文献：
  名称：

  SUDARSANAM, V.;NAGARAJAN, K.;GEORGE, T.;SHENOY, S. J.;IYER, V. V.;KAULGUD+, INDIAN J. CHEM., 1982, 21, N 11, 1022-1026

  摘要：

  DOI：

文献信息

• 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。
• Sudarsanam, V.; Nagarajan, K.; George, T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 11, p. 1022 - 1026
  作者：Sudarsanam, V.、Nagarajan, K.、George, T.、Shenoy, S. J.、Iyer, V. V.、Kaulgud, A. P.

  DOI：——

  日期：——
• Reassignment of the structures of iodonitroimidazole, its N-methyl derivatives, and related compounds
  作者：Jonathan P. Dickens、Robert L. Dyer、Brendan J. Hamill、Terry A. Harrow、Roy H. Bible、Patricia M. Finnegan、Kim Henrick、Philip G. Owston

  DOI：10.1021/jo00322a005

  日期：1981.4
• 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.
• DICKENS J. P.; DYER R. L.; HAMILL B. J.; HARROW T. A.; BIBLE R. H. JR.; F+, J. ORG. CHEM., 1981, 46, NO 9, 1781-1786
  作者：DICKENS J. P.、 DYER R. L.、 HAMILL B. J.、 HARROW T. A.、 BIBLE R. H. JR.、 F+

  DOI：——

  日期：——