(4S^*,9R^*,10R^*)-4-(4-Morpholinyl)-2-aza-3-oxatricyclo<8.3.0.0^4,9>tridec-1-en-5-one-N-oxide | 108831-87-4

• 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: (4S^*,9R^*,10R^*)-4-(4-Morpholinyl)-2-aza-3-oxatricyclo<8.3.0.0^4,9>tridec-1-en-5-one-N-oxide
• 英文别名: (5aS,9aR,9bR)-5a-morpholin-4-yl-4-oxido-1,2,3,7,8,9,9a,9b-octahydrocyclopenta[c][1,2]benzoxazin-4-ium-6-one
• CAS: 108831-87-4；144665-53-2
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: UHHWAYSHFDMJPW-JMSVASOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  64.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S^*,9R^*,10R^*)-4-(4-Morpholinyl)-2-aza-3-oxatricyclo<8.3.0.0^4,9>tridec-1-en-5-one-N-oxide 以 乙腈 为溶剂， 反应 4.0h， 以67%的产率得到(1S^*,3S^*,7R^*,8R^*)-1-(4-Morpholinyl)-3-nitrotricyclo<6.3.0.0^3,7>undecan-2-one
  参考文献：
  名称：

  烯胺酮与1-硝基烯烃的反应。聚喹烷合成的范围和局限性

  摘要：

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.

  DOI：

  10.1016/s0040-4020(01)80490-7
• 作为产物：
  描述：

  1-硝基环戊烯 、 2-(4-吗啉基)环己-2-烯-1-酮 以100%的产率得到(4S^*,9R^*,10R^*)-4-(4-Morpholinyl)-2-aza-3-oxatricyclo<8.3.0.0^4,9>tridec-1-en-5-one-N-oxide
  参考文献：
  名称：

  烯胺酮与1-硝基烯烃的反应。聚喹烷合成的范围和局限性

  摘要：

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.

  DOI：

  10.1016/s0040-4020(01)80490-7

文献信息

• NITTI P.; PITACCO G.; VALENTIN E., VESTN. SLOVEN. KEM. DRUS., 33,(1986) N 3, 251-257
  作者：NITTI P.、 PITACCO G.、 VALENTIN E.

  DOI：——

  日期：——