2-allyl-6-azidohexanal | 950849-58-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-allyl-6-azidohexanal
• 英文别名: 6-Azido-2-prop-2-enylhexanal
• CAS: 950849-58-8
• 化学式: C₉H₁₅N₃O
• 分子量: 181.238
• InChiKey: NTXLTJRYOBOKLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-allyl-6-azidohexanal 在 三氟乙酸 作用下， 以53%的产率得到2-烯丙基-1-哌啶甲醛
  参考文献：
  名称：

  烷基叠氮化物与醛的分子内和分子间施密特反应。

  摘要：

  Despite recent advances in the use of alkyl azides in ring expansion reactions of ketones, there has been little work done on the corresponding chemistry of aldehydes. In the present study, the Lewis acid-promoted reactions of alkyl azides with aldehydes were studied in both intermolecular and intramolecular contexts. The intramolecular reactions of azidoalkyl aldehydes in which the azide and carbonyl groups were separated by 2-5 carbons were examined. Although the examples having the shortest tether failed (3-azidopropanals), each of the other systems gave good yields of either NH-substituted lactams (resulting from hydride migration in the initially formed azidohydrin adduct) or formamides (alkyl migration). The product formed was dependent on the chain length of the starting azido aldehyde. The intermolecular reactions were less efficient, requiring TiCl4 promotion for even moderate yields, and in each case gave mixtures of products resulting from hydride and alkyl migration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.079
• 作为产物：
  描述：

  ethyl 2-allyl-6-azidohexanoate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以81%的产率得到2-allyl-6-azidohexanal
  参考文献：
  名称：

  烷基叠氮化物与醛的分子内和分子间施密特反应。

  摘要：

  Despite recent advances in the use of alkyl azides in ring expansion reactions of ketones, there has been little work done on the corresponding chemistry of aldehydes. In the present study, the Lewis acid-promoted reactions of alkyl azides with aldehydes were studied in both intermolecular and intramolecular contexts. The intramolecular reactions of azidoalkyl aldehydes in which the azide and carbonyl groups were separated by 2-5 carbons were examined. Although the examples having the shortest tether failed (3-azidopropanals), each of the other systems gave good yields of either NH-substituted lactams (resulting from hydride migration in the initially formed azidohydrin adduct) or formamides (alkyl migration). The product formed was dependent on the chain length of the starting azido aldehyde. The intermolecular reactions were less efficient, requiring TiCl4 promotion for even moderate yields, and in each case gave mixtures of products resulting from hydride and alkyl migration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.079