2,3-dimethyl-6-phenylphenanthridine | 1131329-26-4

• 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: 2,3-dimethyl-6-phenylphenanthridine
• 英文别名: 2,3-Dimethyl-6-phenylphenanthridine
• CAS: 1131329-26-4
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: MEZBWCNERKNHCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  二苯甲酮亚胺 、 1,2-二溴-4,5-二甲苯 在 palladium diacetate 、 potassium carbonate 、 三环己基膦 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 9.0h， 以52%的产率得到2,3-dimethyl-6-phenylphenanthridine
  参考文献：
  名称：

  SYNTHESIS OF PHENANTHRIDINES AND RELATED COMPOUNDS BY PALLADIUM-CATALYZED DIRECT COUPLING VIA C–H AND N–H BOND CLEAVAGES

  摘要：

  The palladium-catalyzed direct annulation of benzophenone imines with o-dihalobenzenes proceeds through C-H and N-H bond cleavages to produce 6-arylphenanthridine derivatives. 2-Phenyl-imidazole, -benzimidazole, and -indole also undergo the annulation to form the corresponding tetra- and pentacyclic compounds.

  DOI：

  10.3987/com-12-s(n)45

文献信息

• Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes): Synthesis of Phenanthridines and Isoquinolines
  作者：Thibaud Gerfaud、Luc Neuville、Jieping Zhu

  DOI：10.1002/anie.200804683

  日期：2009.1.5

  Intermolecular insertion: A palladium‐catalyzed domino aminopalladation/ CH functionalization sequence has been developed, and provides access to functionalized phenanthridines and isoquinolines (see scheme; Tf=triflate, TMS=trimethylsilyl, M.S.=molecular sieves). The use of butyronitrile as the solvent is determinant to the success of the domino process.

  分子间插入：钯催化的多米诺aminopalladation / C  ħ官能序列已被开发，并提供访问官能菲啶和异喹啉（参见方案; TF =三氟甲磺酸酯，TMS =三甲基甲硅烷，MS =分子筛）。丁腈作为溶剂的使用决定了多米诺骨牌工艺的成功。
• SYNTHESIS OF PHENANTHRIDINES AND RELATED COMPOUNDS BY PALLADIUM-CATALYZED DIRECT COUPLING VIA C–H AND N–H BOND CLEAVAGES
  作者：Tetsuya Satoh、Masahiro Miura、Daisuke Takeda、Koji Hirano

  DOI：10.3987/com-12-s(n)45

  日期：——

  The palladium-catalyzed direct annulation of benzophenone imines with o-dihalobenzenes proceeds through C-H and N-H bond cleavages to produce 6-arylphenanthridine derivatives. 2-Phenyl-imidazole, -benzimidazole, and -indole also undergo the annulation to form the corresponding tetra- and pentacyclic compounds.