1,4-diphenyl-2-oxa-5-azabicyclo[2.2.2]octan-3-one | 282537-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1,4-diphenyl-2-oxa-5-azabicyclo[2.2.2]octan-3-one
• CAS: 282537-82-0
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: BZULXMPWQFUZDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-diphenyl-2-oxa-5-azabicyclo[2.2.2]octan-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1,2,3,4,5,6-hexahydro-5α-hydroxy-2β,5β-diphenyl-2α-pyridinemethanol
  参考文献：
  名称：

  Stereoselective Transformation of 2H-1,4-Oxazin-2-ones into 2,(2),5,5-Tri- and Tetrasubstituted Analogues of cis-5-Hydroxy-2-piperidinemethanol and cis-5-Hydroxy-6-oxo-2-piperidinecarboxylic Acid

  摘要：

  2,(2),5,5-Tri- and tetrasubstituted analogues of 5-hydroxy-2-piperidinemethanol and 5-hydroxy-6-oxo-2-piperidinecarboxylic acid have been prepared via Diels-Alder reaction of 3-substituted 2H-1,4-oxazin-2-ones with ethene followed by functional group transformation of the resulting imidoyl chloride and lactone groups. Some of the 2-piperidinemethanol products are converted further into potential substance P antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00193-9
• 作为产物：
  描述：

  5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 1,4-diphenyl-2-oxa-5-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  Stereoselective Transformation of 2H-1,4-Oxazin-2-ones into 2,(2),5,5-Tri- and Tetrasubstituted Analogues of cis-5-Hydroxy-2-piperidinemethanol and cis-5-Hydroxy-6-oxo-2-piperidinecarboxylic Acid

  摘要：

  2,(2),5,5-Tri- and tetrasubstituted analogues of 5-hydroxy-2-piperidinemethanol and 5-hydroxy-6-oxo-2-piperidinecarboxylic acid have been prepared via Diels-Alder reaction of 3-substituted 2H-1,4-oxazin-2-ones with ethene followed by functional group transformation of the resulting imidoyl chloride and lactone groups. Some of the 2-piperidinemethanol products are converted further into potential substance P antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00193-9

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.