2-(furan-2'-yl)-1H-phenanthro[9,10-d]imidazole | 36097-72-0

• 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-(furan-2'-yl)-1H-phenanthro[9,10-d]imidazole
• 英文别名: 2-(furan-2-yl)-1H-phenanthro[9,10-d]imidazole；2-(2-furyl)phenanthro[9,10-d]imidazole；2-furan-2-yl-1H-phenanthro[9,10-d]imidazole；2-[2]furyl-1H-phenanthro[9,10-d]imidazole；2-[2]Furyl-1H-phenanthro[9,10-d]imidazol
• CAS: 36097-72-0
• 化学式: C₁₉H₁₂N₂O
• 分子量: 284.317
• InChiKey: XIDAXBQQHLCRHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(furan-2'-yl)-1H-phenanthro[9,10-d]imidazole 在 氢氧化钾 、 溴 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 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：

  糠醛 、 菲醌 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以88%的产率得到2-(furan-2'-yl)-1H-phenanthro[9,10-d]imidazole
  参考文献：
  名称：

  多组分一锅法合成2-芳基-1H-菲[9,10-d]咪唑的新方法

  摘要：

  摘要报道了一种新型的酸催化多组分一锅法合成由芳香醛、9,10-菲醌和醋酸铵衍生的 2-芳基-1H-菲[9,10-d]咪唑化合物在超声辐照下。在优化的条件下，多种芳香醛很容易与 9,10-菲醌和乙酸铵缩合，从而以优异的收率提供所需的高纯度咪唑。

  DOI：

  10.1515/hc.2011.018

文献信息

• New approach to the multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazoles
  作者：Saman Damavandi

  DOI：10.1515/hc.2011.018

  日期：2011.1.1

  Abstract A novel, acid catalyzed multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole compounds derived from aromatic aldehydes, 9,10-phenanthrenequinone and ammonium acetate under ultrasonic irradiation is reported. A wide range of aromatic aldehydes readily undergo condensation with 9,10-phenanthrenequinone and ammonium acetate under optimized conditions to afford the desired

  摘要报道了一种新型的酸催化多组分一锅法合成由芳香醛、9,10-菲醌和醋酸铵衍生的 2-芳基-1H-菲[9,10-d]咪唑化合物在超声辐照下。在优化的条件下，多种芳香醛很容易与 9,10-菲醌和乙酸铵缩合，从而以优异的收率提供所需的高纯度咪唑。
• Dora; Dash; Panda, Journal of the Indian Chemical Society, 1979, vol. 56, # 6, p. 620 - 624
  作者：Dora、Dash、Panda

  DOI：——

  日期：——
• Reactions of Phenanthraquinone and Retenequinone with Aldehydes and Ammonium Acetate in Acetic Acid Solution¹
  作者：Edgar A. Steck、Allan R. Day

  DOI：10.1021/ja01243a043

  日期：1943.3
• 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.
• Schiff Base Transition Metal Complex Catalyzed One-Pot Synthesis of 2-Aryl-1<i>H</i>-phenanthro[9,10-d]imidazoles
  作者：Saman Damavandi

  DOI：10.1080/15533174.2011.594839

  日期：2011.11.1

  A rapid, efficient, and novel methodology for the synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole derivatives, catalyzed by bis[N-(3,5-dicumylsalicylidene)-2',6'-fluoroanilinato]zirconium(IV) dichloride under ultrasonic irradiation at room temperature, is reported. A range of substituted imidazoles was synthesized in excellent yields from one-pot reaction of aromatic aldehydes, 9,10-phenanthrenequinone, and ammonium acetate. The remarkable features of this new procedure are introducing a new one-pot method for synthesis of 2-aryl-1H-phenanthro[9,10-d] imidazoles, high conversion, short reaction time, and simple experimental and workup procedure.