8-(4-methylphenyl)-8-aza-bicyclo[3.2.1]oct-2-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 8-(4-methylphenyl)-8-aza-bicyclo[3.2.1]oct-2-ene
• 英文别名: 8-(4-Methylphenyl)-8-azabicyclo[3.2.1]oct-2-ene；8-(4-methylphenyl)-8-azabicyclo[3.2.1]oct-2-ene
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: GDOFHDSQPMTUEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-(4-methylphenyl)-8-aza-bicyclo[3.2.1]oct-2-ene 、 4-叔丁基苯胺 在 palladium(II) trifluoroacetate 、 苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 66.0h， 以24%的产率得到8-(4-tert-butylphenyl)-8-aza-bicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Tropene Derivatives by Sequential Intermolecular and Transannular, Intramolecular Palladium-Catalyzed Hydroamination of Cycloheptatriene

  摘要：

  A consecutive inter- and intramolecular hydroamination of cycloheptatriene with primary aromatic amines, benzylic amines, and beta-phenethylamines occurs to produce pharmaceutically relevant tropene (8-azabicyclo[3.2.1]octene) frameworks in good to excellent yields. This reaction occurs in the presence of a catalyst generated from palladium trifluoroacetate, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and a mild acid. Mechanistic studies reveal that the overall process has some reversible steps, but that the rate of these reverse reactions are far slower than the rates of the forward catalytic process.

  DOI：

  10.1021/ja061349a
• 作为产物：
  描述：

  乙烷,三氯氟- 、 环庚三烯 在 palladium(II) trifluoroacetate 、 苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以80%的产率得到8-(4-methylphenyl)-8-aza-bicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Tropene Derivatives by Sequential Intermolecular and Transannular, Intramolecular Palladium-Catalyzed Hydroamination of Cycloheptatriene

  摘要：

  A consecutive inter- and intramolecular hydroamination of cycloheptatriene with primary aromatic amines, benzylic amines, and beta-phenethylamines occurs to produce pharmaceutically relevant tropene (8-azabicyclo[3.2.1]octene) frameworks in good to excellent yields. This reaction occurs in the presence of a catalyst generated from palladium trifluoroacetate, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and a mild acid. Mechanistic studies reveal that the overall process has some reversible steps, but that the rate of these reverse reactions are far slower than the rates of the forward catalytic process.

  DOI：

  10.1021/ja061349a

文献信息

• Tropene Derivatives by Sequential Intermolecular and Transannular, Intramolecular Palladium-Catalyzed Hydroamination of Cycloheptatriene
  作者：Norio Sakai、André Ridder、John F. Hartwig

  DOI：10.1021/ja061349a

  日期：2006.6.1

  A consecutive inter- and intramolecular hydroamination of cycloheptatriene with primary aromatic amines, benzylic amines, and beta-phenethylamines occurs to produce pharmaceutically relevant tropene (8-azabicyclo[3.2.1]octene) frameworks in good to excellent yields. This reaction occurs in the presence of a catalyst generated from palladium trifluoroacetate, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and a mild acid. Mechanistic studies reveal that the overall process has some reversible steps, but that the rate of these reverse reactions are far slower than the rates of the forward catalytic process.