4-phenylphenanthridine | 95024-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-phenylphenanthridine
• 英文别名: 4-Phenyl-phenanthridin；4-Phenylphenanthridine
• CAS: 95024-21-8
• 化学式: C₁₉H₁₃N
• 分子量: 255.319
• InChiKey: BZBSUKRKVQIEQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-iodobenzyl)biphenyl-2-amine 在 potassium tert-butylate 作用下， 以 氨 为溶剂， 反应 3.0h， 以87%的产率得到4-phenylphenanthridine
  参考文献：
  名称：

  通过S RN 1反应通过芳基酰胺离子与芳基卤化物的分子内邻位芳基化反应合成菲啶和苯并菲啶

  摘要：

  的光刺激反应ñ - （2-卤代-苄基）芳基胺与吨-BuOK在由S稠合氮杂杂环液氨得到RN 1机构。通过使2-卤代苄基氯与芳族胺反应以制备仲胺，可以容易地获得起始原料。通过这种方法，合成了菲啶（90％），4-苯基菲啶（87％），苯并[ a ]菲啶（98％）和苯并[ c ]菲啶（84％）。

  DOI：

  10.1016/j.tetlet.2007.10.009

文献信息

• Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions
  作者：Maria E. Budén、Roberto A. Rossi

  DOI：10.1016/j.tetlet.2007.10.009

  日期：2007.12

  The photostimulated reaction of N-(2-halo-benzyl)aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the SRN1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo[a]phenanthridine (98%), and benzo[c]phenanthridine

  的光刺激反应ñ - （2-卤代-苄基）芳基胺与吨-BuOK在由S稠合氮杂杂环液氨得到RN 1机构。通过使2-卤代苄基氯与芳族胺反应以制备仲胺，可以容易地获得起始原料。通过这种方法，合成了菲啶（90％），4-苯基菲啶（87％），苯并[ a ]菲啶（98％）和苯并[ c ]菲啶（84％）。
• Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position
  作者：Jaesung Kwak、Min Kim、Sukbok Chang

  DOI：10.1021/ja111670s

  日期：2011.3.23

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.
• Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from <i>N</i>-(<i>ortho</i>-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
  作者：María E. Budén、Viviana B. Dorn、Martina Gamba、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo9025918

  日期：2010.4.2

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.