2-methoxy-1-(2-vinylazocan-1-yl)ethan-1-one

• 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: 2-methoxy-1-(2-vinylazocan-1-yl)ethan-1-one
• 英文别名: 1-(2-Ethenylazocan-1-yl)-2-methoxyethanone；1-(2-ethenylazocan-1-yl)-2-methoxyethanone
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: NYKXDTFFGKLPNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-(2-vinylazocan-1-yl)ethan-1-one 在 lithium hexamethyldisilazane 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.5h， 生成 (E)-3-methoxyazacyclododec-5-en-2-one
  参考文献：
  名称：

  Studies on the aza-Claisen Rearrangement of 7 to 9-Membered Vinylazacycles

  摘要：

  A systematic study on the amide enolate-induced aza-Claisen rearrangement (ACR) of 7 to 9-membered vinylazacycles has been carried out, resulting in an efficient synthetic method to prepare 11 to 13-membered macrolactams. Key feature includes introduction of electron-donating substituents at a-position of the amide substrates possessing 7 to 9-membered vinylazacycles to facilitate amide enolate-induced.ACR. In addition, substituent effects on ACR has been discussed based on the experimental results. We believe this study would provide experimental evidences for the substituent effects and envision for the synthetic application of ACR-induced ring expansion.

  DOI：

  10.3987/com-16-13432
• 作为产物：
  描述：

  tert-butyl 2-vinylazocane-1-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-methoxy-1-(2-vinylazocan-1-yl)ethan-1-one
  参考文献：
  名称：

  Studies on the aza-Claisen Rearrangement of 7 to 9-Membered Vinylazacycles

  摘要：

  A systematic study on the amide enolate-induced aza-Claisen rearrangement (ACR) of 7 to 9-membered vinylazacycles has been carried out, resulting in an efficient synthetic method to prepare 11 to 13-membered macrolactams. Key feature includes introduction of electron-donating substituents at a-position of the amide substrates possessing 7 to 9-membered vinylazacycles to facilitate amide enolate-induced.ACR. In addition, substituent effects on ACR has been discussed based on the experimental results. We believe this study would provide experimental evidences for the substituent effects and envision for the synthetic application of ACR-induced ring expansion.

  DOI：

  10.3987/com-16-13432

文献信息

• Studies on the aza-Claisen Rearrangement of 7 to 9-Membered Vinylazacycles
  作者：Jong-Wha Jung、Young-Ger Suh、Seok-Ho Kim、Won-Il Lee、Seon-Mi Kim、Jae-Kyung Jung、Jaebong Jang、Jaehoon Sim

  DOI：10.3987/com-16-13432

  日期：——

  A systematic study on the amide enolate-induced aza-Claisen rearrangement (ACR) of 7 to 9-membered vinylazacycles has been carried out, resulting in an efficient synthetic method to prepare 11 to 13-membered macrolactams. Key feature includes introduction of electron-donating substituents at a-position of the amide substrates possessing 7 to 9-membered vinylazacycles to facilitate amide enolate-induced.ACR. In addition, substituent effects on ACR has been discussed based on the experimental results. We believe this study would provide experimental evidences for the substituent effects and envision for the synthetic application of ACR-induced ring expansion.