5-azido-2-benzylpentanal | 950849-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-azido-2-benzylpentanal
• CAS: 950849-57-7
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: UDIYLXOPNKGQSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  5-azido-2-benzylpentanal 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-Benzyl-1-formylpyrrolidine
  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：

  5-溴戊酸乙酯 在 正丁基锂 、 sodium azide 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-azido-2-benzylpentanal
  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

文献信息

• Access to 5-bromopentanal and 6-bromohexanal derivatives <i>via</i> the bromination/hydrolysis of C,O-bis-zirconocenes generated from unsaturated Weinreb amides
  作者：Aurélien Coelho、Jean-Bernard Behr、Jean-Luc Vasse

  DOI：10.1039/d2ob01073a

  日期：——

  Access to 5-bromopentanal and 6-bromohexanal derivatives from Weinreb amides is described. The method relies on the sequential C-bromination/zircona-aminal hydrolysis of bis-C,O-zirconocenes, which are generated in situ from unsaturated Weinreb amides using Schwartz's reagent. Synthetic illustrations of such bromo-aldehydes, which can act as carbocycle and heterocycle precursors, are also presented

  描述了从 Weinreb 酰胺中获得 5-溴戊醛和 6-溴己醛衍生物的途径。该方法依赖于使用 Schwartz 试剂从不饱和 Weinreb 酰胺原位生成的双-C、O-锆茂的连续 C-溴化/氧化锆-氨基水解。还介绍了可以作为碳环和杂环前体的这种溴醛的合成说明。