Ethyl 3-azido-4-oxopentanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Ethyl 3-azido-4-oxopentanoate
• 化学式: C₇H₁₁N₃O₃
• mdl: MFCD24453023
• 分子量: 185.183
• InChiKey: FTHUPIUMDIOXJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-azido-4-oxopentanoate 在 乙醛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以34%的产率得到Ethyl 3-amino-4-oxo-2-pentenoate
  参考文献：
  名称：

  Base-Promoted Reactions of .alpha.-Azido Ketones with Aldehydes and Ketones: A Novel Entry to .alpha.-Azido-.beta.-hydroxy Ketones and 2,5-Dihydro-5-hydroxyoxazoles

  摘要：

  The base-promoted reaction of alpha-azido ketones with aldehydes and ketones provides a new and simple route to either alpha-azido-beta-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction, The alpha-azido-beta-hydroxy ketones are formed by an aldol reaction between an enolate of the alpha-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the cx-azido ketone enolate.

  DOI：

  10.1021/jo00113a015
• 作为产物：
  描述：

  Ethyl 3-<((p-nitrophenyl)sulfonyl)oxy>-4-oxopentanoate 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 1.75h， 以94%的产率得到Ethyl 3-azido-4-oxopentanoate
  参考文献：
  名称：

  A General and Efficient Synthesis of .alpha.-Azido Ketones

  摘要：

  DOI：

  10.1021/jo00089a043

文献信息

• Formation of α-enaminoketones from α-azidoketones: An elimination of molecular nitrogen from α-azidoketones
  作者：Karey Van Sant、Michael S. South

  DOI：10.1016/s0040-4039(00)96852-7

  日期：1987.1
• Base-Promoted Reactions of .alpha.-Azido Ketones with Aldehydes and Ketones: A Novel Entry to .alpha.-Azido-.beta.-hydroxy Ketones and 2,5-Dihydro-5-hydroxyoxazoles
  作者：Tamas Patonay、Robert V. Hoffman

  DOI：10.1021/jo00113a015

  日期：1995.4

  The base-promoted reaction of alpha-azido ketones with aldehydes and ketones provides a new and simple route to either alpha-azido-beta-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction, The alpha-azido-beta-hydroxy ketones are formed by an aldol reaction between an enolate of the alpha-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the cx-azido ketone enolate.
• A General and Efficient Synthesis of .alpha.-Azido Ketones
  作者：Tamos Patonay、Robert V. Hoffman

  DOI：10.1021/jo00089a043

  日期：1994.5