(9ci)-1-乙烯-5-硝基-1H-咪唑 | 508235-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-1-乙烯-5-硝基-1H-咪唑
• 英文名称: 5-nitro-1-vinylimidazole
• 英文别名: 5-nitro-1-vinyl-1H-imidazole；1-Ethenyl-5-nitroimidazole
• CAS: 508235-09-4
• 化学式: C₅H₅N₃O₂
• mdl: MFCD18808365
• 分子量: 139.114
• InChiKey: GXIZJYGMSKBSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9ci)-1-乙烯-5-硝基-1H-咪唑 在 甲酸 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 3-hydroxymethyl-5-(5-nitroimidazo-1-yl)isoxazoline
  参考文献：
  名称：

  N-Vinyl-Nitroimidazole Cycloadditions: Potential Routes to Nucleoside Analogues

  摘要：

  研究了 4-硝基和 5-硝基-1-乙烯基咪唑的环加成反应。通过还原成相应的氨基咪唑，得到的环加成物可能成为合成嘌呤核苷类似物的中间体。使用氧化苯腈作为 1,3- 二极亲和剂得到的副产物已被确认为环加载物 11 的新型三环异构体 12。

  DOI：

  10.1055/s-2005-872083
• 作为产物：
  描述：

  1-(2-氯乙基)-5-硝基-1H-咪唑 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以54%的产率得到(9ci)-1-乙烯-5-硝基-1H-咪唑
  参考文献：
  名称：

  Routes toN-vinyl-nitroimidazoles andN-vinyl-deazapurines

  摘要：

  AbstractThe preparations of 4‐ and 5‐nitro‐1‐vinylimidazole (2 and 7) are described. Selective reduction of the nitro group using Fe/dil.HCl is achieved for the 4‐nitro derivative but this is not effective when ethoxymethylenemalononitrile is used to trap the amine. For 5‐nitroimidazole studies the N‐vinyl substituent is kept masked as a 2‐chloroethyl group, which remains unchanged during catalytic reduction of the nitro function (Pd/C), and is revealed by HCl elimination at a later stage. In this way, the 1‐deazapurine 13 and the tricyclic derivative 14 have been prepared.

  DOI：

  10.1002/jhet.5570410508

文献信息

• <i>N</i>-Vinyl-Nitroimidazole Cycloadditions: Potential Routes to Nucleoside Analogues
  作者：Christopher Ramsden、Russell Clayton

  DOI：10.1055/s-2005-872083

  日期：——

  Cycloaddition reactions of 4-nitro- and 5-nitro-1-vinylimidazoles have been investigated. The cycloadducts obtained are potential intermediates for synthesis of purine nucleoside analogues via reduction to the corresponding aminoimidazoles. A byproduct obtained using benzonitrile oxide as 1,3-dipolarophile has been identified as a novel tricyclic isomer 12 of the cycloadduct 11.

  研究了 4-硝基和 5-硝基-1-乙烯基咪唑的环加成反应。通过还原成相应的氨基咪唑，得到的环加成物可能成为合成嘌呤核苷类似物的中间体。使用氧化苯腈作为 1,3- 二极亲和剂得到的副产物已被确认为环加载物 11 的新型三环异构体 12。
• Routes to<i>N</i>-vinyl-nitroimidazoles and<i>N</i>-vinyl-deazapurines
  作者：Russell Clayton、Christopher A. Ramsden

  DOI：10.1002/jhet.5570410508

  日期：2004.9

  AbstractThe preparations of 4‐ and 5‐nitro‐1‐vinylimidazole (2 and 7) are described. Selective reduction of the nitro group using Fe/dil.HCl is achieved for the 4‐nitro derivative but this is not effective when ethoxymethylenemalononitrile is used to trap the amine. For 5‐nitroimidazole studies the N‐vinyl substituent is kept masked as a 2‐chloroethyl group, which remains unchanged during catalytic reduction of the nitro function (Pd/C), and is revealed by HCl elimination at a later stage. In this way, the 1‐deazapurine 13 and the tricyclic derivative 14 have been prepared.