ethyl 3-tert-butyl-2,4,6-cycloheptatrienecarboxylate | 1438848-33-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 3-tert-butyl-2,4,6-cycloheptatrienecarboxylate
• CAS: 1438848-33-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: POGVVHVBGHJQNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 叔丁基苯 在 Ag₃(μ₂-(3,5-(CF₃)₂PyrPy))₃ 作用下， 以 二氯甲烷-D2 为溶剂， 反应 24.0h， 生成 ethyl 3-tert-butyl-2,4,6-cycloheptatrienecarboxylate 、 ethyl 4-tert-butyl-2,4,6-cycloheptatrienecarboxylate
  参考文献：
  名称：

  Büchner Reactions Catalyzed by a Silver(I) Pyridylpyrrolide: Understanding Arene C═C Insertion Selectivity

  摘要：

  The complex Ag-3(mu(2)-3,5-(CF3)(2)PyrPy)(3) (3,5-(CF3)(2)PyrPy = 2,2'-pyridylpyrrolide(1-) ligand) catalytically promotes the insertion of the carbene of ethyl diazoacetate (EDA), at room temperature, into the C=C bond of a series of arenes to ultimately ring-open them and form the corresponding cycloheptatrienes. In one case, the norcaradiene intermediate can be isolated, while regioselective C=C insertion can be promoted with certain arene substrates. The mechanism of C=C insertion, preference over C-H insertion, and origin of C=C regioselectivity has been probed by a combination of experimental and theoretical studies.

  DOI：

  10.1021/om301240d