N-(1,3-dioxobutyl)-piperidine-2-carboxaldehyde-O-methyloxime | 245051-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(1,3-dioxobutyl)-piperidine-2-carboxaldehyde-O-methyloxime
• 英文别名: 1-[2-(methoxyiminomethyl)piperidin-1-yl]butane-1,3-dione
• CAS: 245051-72-3
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: LBGZEZPMLUJJGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(1,3-dioxobutyl)-piperidine-2-carboxaldehyde-O-methyloxime 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 1.0h， 以88%的产率得到6a-acetyl-1-methoxy-octahydro-1,5a-diaza-cyclopropa[a]inden-6-one
  参考文献：
  名称：

  Intramolecular Aziridination:  Decomposition of Diazoamides with Tethered Imino Bonds

  摘要：

  Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo[5.1.0]hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo-transfer reaction, rather than the catalyzed carbenoid reaction.

  DOI：

  10.1021/ol990750h
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl-piperidine-2-carboxaldehyde-O-methyloxime 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 N-(1,3-dioxobutyl)-piperidine-2-carboxaldehyde-O-methyloxime
  参考文献：
  名称：

  Intramolecular Aziridination:  Decomposition of Diazoamides with Tethered Imino Bonds

  摘要：

  Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo[5.1.0]hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo-transfer reaction, rather than the catalyzed carbenoid reaction.

  DOI：

  10.1021/ol990750h