5-(1-甲基苯并咪唑-2-基)硒吩-2-甲醛 | 89155-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 5-(1-甲基苯并咪唑-2-基)硒吩-2-甲醛
• 英文名称: 2-(1-methyl-1H-benzimidazol-2-yl)selenophene-5-carbaldehyde
• 英文别名: 1-methyl-2-(5'-formyl-2'-selenienyl)benzimidazole；5-(1-Methyl-1H-benzimidazol-2-yl)selenophene-2-carbaldehyde；5-(1-methylbenzimidazol-2-yl)selenophene-2-carbaldehyde
• CAS: 89155-27-1
• 化学式: C₁₃H₁₀N₂OSe
• 分子量: 289.195
• InChiKey: NEBPEDUFUJEXLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-甲基苯并咪唑-2-基)硒吩-2-甲醛 在 potassium dichromate 、 硫酸 作用下， 以 水 为溶剂， 以34%的产率得到1-methyl-2-(5'-carboxy-2'-selenienyl)benzimidazole
  参考文献：
  名称：

  Oxidation products of fused 2-hetarylimidazole derivatives

  摘要：

  Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1-methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)-hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro-[9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. pi-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen.

  DOI：

  10.1134/s1070363211080226
• 作为产物：
  描述：

  2-甲酰硒酚 在 氢氧化钾 、 PPA 、 硫化氢 、 copper diacetate 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 5-(1-甲基苯并咪唑-2-基)硒吩-2-甲醛
  参考文献：
  名称：

  2-杂芳基苯并咪唑的化学领域的研究。6. 1-甲基-2-（2'-硒烯基）苯并咪唑的合成及性质

  摘要：

  DOI：

  10.1007/bf00515361

文献信息

• Synthesis of novel fluorescent 2,5-di(benzimidazol-2-yl) derivatives of furan, thiophene, selenophene, and 2,4-di(benzimidazol-2-yl)pyrrole
  作者：M. M. El’chaninov、A. A. Aleksandrov

  DOI：10.1134/s107036321605039x

  日期：2016.5

  thienylbenzazoles has shown that 2,5-di(benzimidazol-2-yl)derivatives of five-membered heterocycles with one heteroatom are promising from the viewpoint of requirements to fluorescent dyes and biological fluorescent probes. In the present work, we synthesized the 2,5-dibenzimidazolyl derivatives of furan, thiophene, selenophene and pyrrole.

  对furyland噻吩基苯并唑类的电子和光谱性质的研究表明，从对荧光染料和生物荧光探针的要求来看，具有一个杂原子的五元杂环的2,5-二(苯并咪唑-2-基)衍生物是很有前景的。在目前的工作中，我们合成了呋喃、噻吩、硒吩和吡咯的 2,5-二苯并咪唑基衍生物。
• Chemistry of 2-hetarylbenzimidazoles. 8. Synthesis and properties of 1-methyl-2-(5?-methyl-2?-selenienyl)benzimidazole
  作者：M. M. El'chaninov、A. M. Simonov、N. N. Magdesieva、A. Ya. Kaminskii

  DOI：10.1007/bf00472255

  日期：1987.12
• ELCHANINOV, M. M.;MAGDESIEVA, N. N.;SIMONOV, A. M.;CHOVNIKOVA, N. G., XIMIYA GETEROTSIKL. SOEDIN., 1983, N 11, 1531-1534
  作者：ELCHANINOV, M. M.、MAGDESIEVA, N. N.、SIMONOV, A. M.、CHOVNIKOVA, N. G.

  DOI：——

  日期：——
• ELCHANINOV, M. M.;SIMONOV, A. M.;MAGDESIEVA, N. N.;KAMINSKIJ, A. YA., XIMIYA GETEROTSIKL. SOED.,(1987) N 12, 1636-1639
  作者：ELCHANINOV, M. M.、SIMONOV, A. M.、MAGDESIEVA, N. N.、KAMINSKIJ, A. YA.

  DOI：——

  日期：——
• Oxidation products of fused 2-hetarylimidazole derivatives
  作者：A. A. Aleksandrov、A. P. Savost’yanov、M. M. El’chaninov、G. V. Salamatina

  DOI：10.1134/s1070363211080226

  日期：2011.8

  Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1-methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)-hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro-[9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. pi-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen.