(1S,5R,6S)-tert-butyl 6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate | 1444211-67-9

• 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: (1S,5R,6S)-tert-butyl 6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 1444211-67-9
• 化学式: C₁₇H₂₂BrNO₃
• 分子量: 368.271
• InChiKey: ABRTWJMTJBDIQS-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,5R,6S)-tert-butyl 6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 4.0h， 以60%的产率得到(1S,5R,6S)-6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane hydrochloride
  参考文献：
  名称：

  Enantioselective Hydroarylation of Bridged [3.2.1] Heterocycles: An Efficient Entry into the Homoepibatidine Skeleton

  摘要：

  Achiral [3.2.1] bridged heterocycles containing a bridging amide can undergo enantioselective hydroarylation reactions under rhodium(I) catalysis. These reactions proceed in high yield and enantioselectivity in most cases, under mild reaction conditions and using commercially available Josiphos ligands. The phosphine ligand structure and the protecting group on the nitrogen both have significant effects on the selectivity and yield of the reactions.

  DOI：

  10.1021/ol401477r
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 吡啶 、 [Rh(OH)(cod)]2 、 (S,R)-PPF-P(t-Bu)2 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 32.25h， 生成 (1S,5R,6S)-tert-butyl 6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate 、 (1R,5S,6R)-tert-butyl 6-(3-bromophenyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate
  参考文献：
  名称：

  Enantioselective Hydroarylation of Bridged [3.2.1] Heterocycles: An Efficient Entry into the Homoepibatidine Skeleton

  摘要：

  Achiral [3.2.1] bridged heterocycles containing a bridging amide can undergo enantioselective hydroarylation reactions under rhodium(I) catalysis. These reactions proceed in high yield and enantioselectivity in most cases, under mild reaction conditions and using commercially available Josiphos ligands. The phosphine ligand structure and the protecting group on the nitrogen both have significant effects on the selectivity and yield of the reactions.

  DOI：

  10.1021/ol401477r