1-(1-(3',4'-dimethoxy-1,1'-biphenyl-2-yl)-3-(4-(tert-butyl)-phenyl)-prop-2-ynyl)-piperidine | 1346143-37-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(1-(3',4'-dimethoxy-1,1'-biphenyl-2-yl)-3-(4-(tert-butyl)-phenyl)-prop-2-ynyl)-piperidine
• 英文别名: 1-[3-(4-Tert-butylphenyl)-1-[2-(3,4-dimethoxyphenyl)phenyl]prop-2-ynyl]piperidine；1-[3-(4-tert-butylphenyl)-1-[2-(3,4-dimethoxyphenyl)phenyl]prop-2-ynyl]piperidine
• CAS: 1346143-37-0
• 化学式: C₃₂H₃₇NO₂
• 分子量: 467.651
• InChiKey: ZNRWNSWCNOXKKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-(3',4'-dimethoxy-1,1'-biphenyl-2-yl)-3-(4-(tert-butyl)-phenyl)-prop-2-ynyl)-piperidine 在 copper(l) iodide 、 三氟乙酸 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到2,3-dimethoxy-10-(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
• 作为产物：
  描述：

  3,4-二甲氧基苯硼酸 在 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 5.0h， 生成 1-(1-(3',4'-dimethoxy-1,1'-biphenyl-2-yl)-3-(4-(tert-butyl)-phenyl)-prop-2-ynyl)-piperidine
  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