ethyl 5-bromo-3-ethxl-9-oxo-3-azabicyclo<3.3.1>nonanecarboxylate | 128164-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 5-bromo-3-ethxl-9-oxo-3-azabicyclo<3.3.1>nonanecarboxylate
• 英文别名: ethyl 5-bromo-3-ethyl-9-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate
• CAS: 128164-63-6
• 化学式: C₁₃H₂₀BrNO₃
• 分子量: 318.211
• InChiKey: SVRAKJZSBSLXJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 ethyl 5-bromo-3-ethxl-9-oxo-3-azabicyclo<3.3.1>nonanecarboxylate 以 四氢呋喃 为溶剂， 以85%的产率得到ethyl 5-bromo-3-ethyl-9-hydroxy-9-methyl-3-azabicyclo[3.3.1]nonane-1-carboxylate
  参考文献：
  名称：

  Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene

  摘要：

  A synthesis of modhephene has been achieved, the key feature of which is the use of a novel nucleophilic addition/rearrangement reaction to develop the carbon framework. Stereochemical control of the stereogenic center bearing the methyl group was accomplished by variation of the hydrogenation conditions. As a byproduct of this work, we have clarified structural assignments of intermediates from previous syntheses.

  DOI：

  10.1021/jo00013a014
• 作为产物：
  描述：

  聚合甲醛 、 3-溴-2-氧-环己酮甲酸乙酯 、 乙胺 以 甲醇 为溶剂， 反应 48.0h， 以49%的产率得到ethyl 5-bromo-3-ethxl-9-oxo-3-azabicyclo<3.3.1>nonanecarboxylate
  参考文献：
  名称：

  Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene

  摘要：

  A synthesis of modhephene has been achieved, the key feature of which is the use of a novel nucleophilic addition/rearrangement reaction to develop the carbon framework. Stereochemical control of the stereogenic center bearing the methyl group was accomplished by variation of the hydrogenation conditions. As a byproduct of this work, we have clarified structural assignments of intermediates from previous syntheses.

  DOI：

  10.1021/jo00013a014

文献信息

• Bridgehead radicals in organic, chemistry. An efficient construction of the ABDE ring system of the lycoctonine alkaloids
  作者：George A. Kraus、Brad Andersh、Qiaogong Su、Jianmin Shi

  DOI：10.1016/s0040-4039(00)60766-9

  日期：1993.3

  The reaction of bridgehead radicals with allylic stannanes generates an intermediate for the synthesis of the ABDE ring of the lycoctonine alkaloids.
• KRAUS, GEORGE A.;SHI, JIANMIN, J. ORG. CHEM., 56,(1991) N3, C. 4147-4151
  作者：KRAUS, GEORGE A.、SHI, JIANMIN

  DOI：——

  日期：——