2-(2-furyl)-1-methylphenanthro[9,10-d]imidazole | 141989-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-(2-furyl)-1-methylphenanthro[9,10-d]imidazole
• 英文别名: 2-(2-Furyl)-1-methyl-1H-phenanthro[9,10-d]imidazole；2-(furan-2-yl)-3-methylphenanthro[9,10-d]imidazole
• CAS: 141989-40-4
• 化学式: C₂₀H₁₄N₂O
• mdl: MFCD01238722
• 分子量: 298.344
• InChiKey: WKQLQLLFJBITQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  545.2±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-furyl)-1-methylphenanthro[9,10-d]imidazole 在 溴 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以74%的产率得到2-(5-bromo-2-furyl)-1-methylphenanthro[9,10-d]imidazole
  参考文献：
  名称：

  2-（2-呋喃基）-和2-（2-噻吩基）-1-甲基菲[9,10-d]咪唑的合成及性质

  摘要：

  Condensation of 9,10-phenanthrenequinone with 2-furaldehyde and 2-thiophenecarbaldehyde in glacial acetic acid in the presence of ammonium acetate gave 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles which were converted into the corresponding 1-methyl derivatives. The furan and thiophene rings in the products lose their acidophobic properties. Depending on the conditions, electrophilic substitution reactions in 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles occur both at the furan (thiophene) and phenanthrene moieties.

  DOI：

  10.1023/a:1019623408687
• 作为产物：
  描述：

  菲醌 在 ammonium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(2-furyl)-1-methylphenanthro[9,10-d]imidazole
  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

文献信息

• Investigations of 2-substituted imidazoles. 2. Synthesis and electrophilic substitution of 1-methyl-2-(thienyl-2)imidazole. A convenient method of methylation of 2-R-imidazoles
  作者：V. M. Stoyanov、M. M. El'chaninov、A. F. Pozharskii

  DOI：10.1007/bf00486814

  日期：1991.10
• Synthesis of Formyl Derivatives of 2-Hetarylimidazoles Annelated with Naphthalene and Phenanthrene Rings
  作者：A. A. Pechkin、M. M. Elchaninov、B. S. Lukyanov、Yu. S. Alekseenko

  DOI：10.1023/b:cohc.0000037315.48485.a2

  日期：2004.5
• CH-alkylation of furan derivatives under photoinduced Pd catalysis
  作者：Igor V. Lavrentev、Konstantin E. Shepelenko、Irina G. Gnatiuk、Andrey A. Aleksandrov、Yu Zhang、Victor M. Chernyshev

  DOI：10.1016/j.mencom.2023.06.017

  日期：2023.7
• 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.
• ——
  作者：A. A. Pechkin、M. M. El'chaninov、V. M. Stoyanov

  DOI：10.1023/a:1019623408687

  日期：——

  Condensation of 9,10-phenanthrenequinone with 2-furaldehyde and 2-thiophenecarbaldehyde in glacial acetic acid in the presence of ammonium acetate gave 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles which were converted into the corresponding 1-methyl derivatives. The furan and thiophene rings in the products lose their acidophobic properties. Depending on the conditions, electrophilic substitution reactions in 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles occur both at the furan (thiophene) and phenanthrene moieties.