7-Methoxy-undec-10-en-5-ynal | 910482-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Methoxy-undec-10-en-5-ynal
• CAS: 910482-87-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: SDYZCLPILTYJRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-Methoxy-undec-10-en-5-ynal 在 Oxone 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以455 mg的产率得到7-methoxyundec-10-en-5-ynoic acid
  参考文献：
  名称：

  Nicholas Reactions with Carboxylic Acids for the Synthesis of Macrocyclic Diolides

  摘要：

  [GRAPHIC]We have developed a new strategy for the preparation of diolides using a cascade of Nicholas reactions. The carboxylic acid nucleophiles in these reactions are virtually unstudied participants in transformations of this type. Using this methodology, a 16-membered cobalt-complexed cyclic diyne is available in 28% yield over eight steps (an average of 85% per step). We can also easily access the uncomplexed diolide in one additional step.

  DOI：

  10.1021/jo051691q
• 作为产物：
  描述：

  2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 在 乙基溴化镁 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 7-Methoxy-undec-10-en-5-ynal
  参考文献：
  名称：

  Nicholas Reactions with Carboxylic Acids for the Synthesis of Macrocyclic Diolides

  摘要：

  [GRAPHIC]We have developed a new strategy for the preparation of diolides using a cascade of Nicholas reactions. The carboxylic acid nucleophiles in these reactions are virtually unstudied participants in transformations of this type. Using this methodology, a 16-membered cobalt-complexed cyclic diyne is available in 28% yield over eight steps (an average of 85% per step). We can also easily access the uncomplexed diolide in one additional step.

  DOI：

  10.1021/jo051691q