2,3-dimethoxy-9-(4-(tert-butyl)benzyl)phenanthrene | 1346143-33-6

• 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: 2,3-dimethoxy-9-(4-(tert-butyl)benzyl)phenanthrene
• 英文别名: 9-[(4-Tert-butylphenyl)methyl]-2,3-dimethoxyphenanthrene
• CAS: 1346143-33-6
• 化学式: C₂₇H₂₈O₂
• 分子量: 384.518
• InChiKey: KNKQOJLKGBAVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯硼酸 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 sodium carbonate 、 三氟乙酸 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2,3-dimethoxy-9-(4-(tert-butyl)benzyl)phenanthrene
  参考文献：
  名称：

  One-Pot Zn/CuI/TFA-Catalyzed Domino Three-Component–Carbocyclization Reaction Involving Biphenyl-2-carbaldehydes/Alkynes/Piperidine: Allenes-Mediated Construction of Phenanthrenes

  摘要：

  A one-pot protocol involving Zn/CuI/TFA-catalyzed domino three-component and subsequent carbocyclization reactions is described. The reaction proceeds via formation of propargyl amines from biphenyl-2-carbaldehydes/terminal alkynes/piperidine followed by the elimination of piperidine and ring closure to furnish phenanthrene derivatives in good yields. The strategy involves C(sp)-H activation-CH functionalization with imine-alkyne activation-1,5 hydride shift-beta-elimination of piperidine-allene formation-6 pi cycloaddition isomerization domino sequence. Evidence for the involvement of allenes as an intermediate during carbocyclization is discussed.

  DOI：

  10.1021/jo201942r

文献信息

• One-Pot Zn/CuI/TFA-Catalyzed Domino Three-Component–Carbocyclization Reaction Involving Biphenyl-2-carbaldehydes/Alkynes/Piperidine: Allenes-Mediated Construction of Phenanthrenes
  作者：Mohammad Saifuddin、Piyush K. Agarwal、Bijoy Kundu

  DOI：10.1021/jo201942r

  日期：2011.12.16

  A one-pot protocol involving Zn/CuI/TFA-catalyzed domino three-component and subsequent carbocyclization reactions is described. The reaction proceeds via formation of propargyl amines from biphenyl-2-carbaldehydes/terminal alkynes/piperidine followed by the elimination of piperidine and ring closure to furnish phenanthrene derivatives in good yields. The strategy involves C(sp)-H activation-CH functionalization with imine-alkyne activation-1,5 hydride shift-beta-elimination of piperidine-allene formation-6 pi cycloaddition isomerization domino sequence. Evidence for the involvement of allenes as an intermediate during carbocyclization is discussed.