(1R,6S,7S,9R)-ethyl 9-(3-chlorophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate | 1549574-75-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,6S,7S,9R)-ethyl 9-(3-chlorophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate
• CAS: 1549574-75-5
• 化学式: C₁₈H₁₈ClNO₃
• 分子量: 331.799
• InChiKey: VEPDUFMOPFLQIR-UGUYLWEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-氯苯甲醛 在 tetrakis(acetonitrile)copper(I) perchlorate 、 (R)-N,N-二甲基-1-[(S)-2-(二苯基膦基)二茂铁基]乙胺 、 magnesium sulfate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (1R,6S,7S,9R)-ethyl 9-(3-chlorophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate 、 ethyl 9-(3-chlorophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate 、 ethyl 9-(3-chlorophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate
  参考文献：
  名称：

  Metal-Catalyzed [6 + 3] Cycloaddition of Tropone with Azomethine Ylides: A Practical Access to Piperidine-Fused Bicyclic Heterocycles

  摘要：

  The first metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides has been developed. With the use of a chiral ferrocenylphosphine-copper(I) complex as the catalyst, the asymmetric variant of the [6 + 3] cycloaddition has also been successfully achieved. The reactions proceeded smoothly under mild conditions, affording piperidine-fused bicyclic heterocycles in moderate to high yields with good to excellent diastereo- and enantioselectivies. The procedures are operationally simple and the catalysts are cheap and readily accessible, thus providing a practical approach to piperidine-fused bicyclic heterocycles.

  DOI：

  10.1021/ja4122268