2-(3-nitrophenyl)-4-phenyl-9-methyl-1-oxa-3,9-diazaspiro<5.5>undecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 2-(3-nitrophenyl)-4-phenyl-9-methyl-1-oxa-3,9-diazaspiro<5.5>undecane
• 英文别名: (2S,4R)-9-methyl-2-(3-nitrophenyl)-4-phenyl-1-oxa-3,9-diazaspiro[5.5]undecane
• 化学式: C₂₁H₂₅N₃O₃
• 分子量: 367.448
• InChiKey: YCPZKZVVTDNDJE-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲腈 N-氧化物 在 lithium aluminium tetrahydride 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 114.0h， 生成 2-(3-nitrophenyl)-4-phenyl-9-methyl-1-oxa-3,9-diazaspiro<5.5>undecane
  参考文献：
  名称：

  Synthesis of spiro-substituted 1,3-oxazines by a new sequence leading to spiroheterocycles

  摘要：

  The target compounds, i.e. 1,3-oxazines which are spiro-substituted in position 6 by a piperidine moiety, are derived from 1-oxa-3,9-diaza-spiro [5.5]undecane, a novel heterocyclic parent system. They were all approached by the following three-step sequence: 1,3-dipolar cycloadditions of nitrile oxides and nitrones to piperidines bearing an exocyclic methylene group gave the corresponding spiro-substituted oxazole derivatives 3. In a consecutive step these were cleaved by hydrogenolysis to gamma-amino-alcohols 4, which in a final step were recyclized by insertions of a C-1-unit to yield the target structures 5-10: thus a de facto ring-extension of spiro-oxazoles to spiro-oxazines was accomplished.

  DOI：

  10.1007/bf00812705

文献信息

• Synthesis of spiro-substituted 1,3-oxazines by a new sequence leading to spiroheterocycles
  作者：L. Fišera、F. Sauter、J. Fröhlich、Y. Feng、K. Mereiter

  DOI：10.1007/bf00812705

  日期：1994.8

  The target compounds, i.e. 1,3-oxazines which are spiro-substituted in position 6 by a piperidine moiety, are derived from 1-oxa-3,9-diaza-spiro [5.5]undecane, a novel heterocyclic parent system. They were all approached by the following three-step sequence: 1,3-dipolar cycloadditions of nitrile oxides and nitrones to piperidines bearing an exocyclic methylene group gave the corresponding spiro-substituted oxazole derivatives 3. In a consecutive step these were cleaved by hydrogenolysis to gamma-amino-alcohols 4, which in a final step were recyclized by insertions of a C-1-unit to yield the target structures 5-10: thus a de facto ring-extension of spiro-oxazoles to spiro-oxazines was accomplished.