1-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one | 400758-85-2

• 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: 1-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one
• CAS: 400758-85-2
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: QJJPXWZYJXCRJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.26
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  邻甲氧基苄胺 、 1-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one 以 四氢呋喃 为溶剂， 反应 24.0h， 以58%的产率得到5α-hydroxy-N²-(2-methoxybenzyl)-5β-methyl-2β-(1-methyl-1H-pyrrol-2-yl)-2α-piperidinecarboxamide
  参考文献：
  名称：

  Stereoselective conversion of 2 H -1,4-oxazin-2-ones into 2,5,5-substituted piperidine-2-carboxamides and 2-methanamines and related octahydro-2 H -pyrido[1,2- a ]pyrazines, potential substance P antagonists

  摘要：

  4-(Hetero)aryl-2-oxa-5-azabicyclo[2.2.2] octan-3-ones and 3,6-diones, formed via cycloaddition of 2H-1,4-oxazin-2-ones and ethene followed by functional group transformation, undergo lactone cleavage by reaction with amines to yield substituted 2-(hetero)aryl-5-hydroxy-2-piperidinecarboxamides. Subsequent reduction affords the corresponding 2-piperidinemethanamines. Both amide and amine compounds are of interest as potential Substance P antagonists. A detailed NMR study, supported by conformational calculations, of an octahydro-2H-pyrido[1,2-a]pyrazine analogue revealed the existence of a temperature and solvent dependent equilibrium mixture of transoid and cisoid invertomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00888-2
• 作为产物：
  描述：

  3,5-二氯-6-甲基-1,4-噁唑-2-酮 在 palladium on activated charcoal 三乙烯二胺 、 盐酸 、 氢气 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 20.0~110.0 ℃ 、303.98 kPa 条件下， 反应 4.0h， 生成 1-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  Stereoselective conversion of 2 H -1,4-oxazin-2-ones into 2,5,5-substituted piperidine-2-carboxamides and 2-methanamines and related octahydro-2 H -pyrido[1,2- a ]pyrazines, potential substance P antagonists

  摘要：

  4-(Hetero)aryl-2-oxa-5-azabicyclo[2.2.2] octan-3-ones and 3,6-diones, formed via cycloaddition of 2H-1,4-oxazin-2-ones and ethene followed by functional group transformation, undergo lactone cleavage by reaction with amines to yield substituted 2-(hetero)aryl-5-hydroxy-2-piperidinecarboxamides. Subsequent reduction affords the corresponding 2-piperidinemethanamines. Both amide and amine compounds are of interest as potential Substance P antagonists. A detailed NMR study, supported by conformational calculations, of an octahydro-2H-pyrido[1,2-a]pyrazine analogue revealed the existence of a temperature and solvent dependent equilibrium mixture of transoid and cisoid invertomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00888-2

文献信息

• Stereoselective conversion of 2 H -1,4-oxazin-2-ones into 2,5,5-substituted piperidine-2-carboxamides and 2-methanamines and related octahydro-2 H -pyrido[1,2- a ]pyrazines, potential substance P antagonists
  作者：Joeri Rogiers、Xiujuan Wu、Suzanne Toppet、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/s0040-4020(01)00888-2

  日期：2001.10

  4-(Hetero)aryl-2-oxa-5-azabicyclo[2.2.2] octan-3-ones and 3,6-diones, formed via cycloaddition of 2H-1,4-oxazin-2-ones and ethene followed by functional group transformation, undergo lactone cleavage by reaction with amines to yield substituted 2-(hetero)aryl-5-hydroxy-2-piperidinecarboxamides. Subsequent reduction affords the corresponding 2-piperidinemethanamines. Both amide and amine compounds are of interest as potential Substance P antagonists. A detailed NMR study, supported by conformational calculations, of an octahydro-2H-pyrido[1,2-a]pyrazine analogue revealed the existence of a temperature and solvent dependent equilibrium mixture of transoid and cisoid invertomers. (C) 2001 Elsevier Science Ltd. All rights reserved.