(1R,3S,4S)-3-(3-azidopropyl)bicyclo[2.2.1]hept-5-en-2-one | 1187565-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,4S)-3-(3-azidopropyl)bicyclo[2.2.1]hept-5-en-2-one
• CAS: 1187565-43-0
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: JOGLFWWUQRNHTJ-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S)-3-(3-azidopropyl)bicyclo[2.2.1]hept-5-en-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(1S,2S,8R)-6-azatricyclo[6.2.1.02,6]undec-9-en-7-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Alkaloids 223A and 6-epi-223A

  摘要：

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.

  DOI：

  10.1021/ol901645j
• 作为产物：
  描述：

  (1R,3S,4S)-3-(3-chloropropyl)bicyclo[2.2.1]hept-5-en-2-one 在 sodium azide 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以90%的产率得到(1R,3S,4S)-3-(3-azidopropyl)bicyclo[2.2.1]hept-5-en-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Alkaloids 223A and 6-epi-223A

  摘要：

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.

  DOI：

  10.1021/ol901645j

文献信息

• Asymmetric Total Synthesis of Alkaloids 223A and 6-<i>epi</i>-223A
  作者：Partha Ghosh、Weston R. Judd、Timothy Ribelin、Jeffrey Aubé

  DOI：10.1021/ol901645j

  日期：2009.9.17

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.