9-benzyl-2,3-dimethoxyphenanthrene | 1346143-34-7

• 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: 9-benzyl-2,3-dimethoxyphenanthrene
• CAS: 1346143-34-7
• 化学式: C₂₃H₂₀O₂
• 分子量: 328.411
• InChiKey: QCWGRMPURHRPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  6-溴藜芦醛 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 9-benzyl-2,3-dimethoxyphenanthrene
  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

• Tandem Ene/[4 + 2] Cycloaddition Reaction for the Synthesis of 9-Benzylphenanthrenes from Arynes and α-(Bromomethyl)styrenes
  作者：Yun Sa、Xin Lv、Jia-Yu Yao、Xu-Yang Lu、Ai-Bin Wu、Wen-Ming Shu、Wei-Chu Yu

  DOI：10.1021/acs.joc.3c00051

  日期：2023.7.7

  A tandem reaction for the synthesis of phenanthrenes from arynes and α-(bromomethyl)styrenes is reported. The transformation proceeds via an ene reaction of α-(bromomethyl)styrenes with arynes, followed by a [4 + 2] cycloaddition reaction. The reaction generates 9-benzylphenanthrene derivatives in moderate to excellent yields.

  报道了由芳炔和 α-(溴甲基)苯乙烯合成菲的串联反应。该转化通过 α-(溴甲基)苯乙烯与芳烃的烯反应进行，然后进行 [4 + 2] 环加成反应。该反应以中等至优异的收率生成 9-苄基菲衍生物。