4-[1-(4-Chlorophenyl)-3-oxo-3-phenyl-2-pyridin-1-ium-1-ylpropyl]-3-phenyl-1,2-oxazol-5-olate | 335373-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[1-(4-Chlorophenyl)-3-oxo-3-phenyl-2-pyridin-1-ium-1-ylpropyl]-3-phenyl-1,2-oxazol-5-olate
• 英文别名: 4-[1-(4-chlorophenyl)-3-oxo-3-phenyl-2-pyridin-1-ium-1-ylpropyl]-3-phenyl-1,2-oxazol-5-olate
• CAS: 335373-29-0
• 化学式: C₂₉H₂₁ClN₂O₃
• 分子量: 480.95
• InChiKey: VJUBEKOOPMTOFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[1-(4-Chlorophenyl)-3-oxo-3-phenyl-2-pyridin-1-ium-1-ylpropyl]-3-phenyl-1,2-oxazol-5-olate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到4-[1-(4-Chlorophenyl)-2-(1-pyridinio)ethyl]-phenylisoxazolium-5-olate
  参考文献：
  名称：

  吡啶鎓吡啶盐与（芳基亚甲基）异恶唑-5-酮的迈克尔加成反应与1,3-环加成反应：4- [1-芳基-2-（1-吡啶并乙基）乙基]异恶唑鎓5-油酸酯的非对映选择性形成

  摘要：

  （芳基亚甲基）异恶唑-5-酮1与吡啶鎓吡啶盐2的反应导致油酸酯4的非对映选择性形成。基于X射线分析以及1 H-NMR和化学证据，讨论了有利于Michael加成反应以及随后未能成功环化为稠合的O杂环的原因。

  DOI：

  10.1002/jlac.199719970224
• 作为产物：
  描述：

  (Z)-4-(4-chlorobenzylidene)-3-phenylisoxazol-5(4H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸铵 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 4-[1-(4-Chlorophenyl)-3-oxo-3-phenyl-2-pyridin-1-ium-1-ylpropyl]-3-phenyl-1,2-oxazol-5-olate
  参考文献：
  名称：

  Pyridinium N-Ylides and (Arylmethylene)azol-5-ones. Reaction Cascade Leading to an Unusual Spiroisoxazolinone Ring

  摘要：

  The reaction of a series of (arylmethylene)azol-5-ones with phenacylpyridinium salt 3 in glacial acetic acid/ammonium acetate mixture gives different results depending on the starting azolone. The isoxazol-5-ones 1 give the unusual spirans 6 in a reaction cascade involving Michael- and retro-Michael reactions, C-alkylation, aldol addition, and diastereospecific cyclization. The reaction performed with oxazol-5-ones 11 has shown that a literature re po rt has to he corrected since no oxazolopyridines 12 hut rather arylideneimidazol-5-ones 13 are produced. In the case of pyrazolin-5-ones 14, the unavoidable formation of bis-adducts 15 always prevents any other type of reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00921-2

文献信息

• Pyridinium N-Ylides and (Arylmethylene)azol-5-ones. Reaction Cascade Leading to an Unusual Spiroisoxazolinone Ring
  作者：Francesco Risitano、Giovanni Grassi、Francesco Foti、Cristina Bilardo

  DOI：10.1016/s0040-4020(00)00921-2

  日期：2000.12

  The reaction of a series of (arylmethylene)azol-5-ones with phenacylpyridinium salt 3 in glacial acetic acid/ammonium acetate mixture gives different results depending on the starting azolone. The isoxazol-5-ones 1 give the unusual spirans 6 in a reaction cascade involving Michael- and retro-Michael reactions, C-alkylation, aldol addition, and diastereospecific cyclization. The reaction performed with oxazol-5-ones 11 has shown that a literature re po rt has to he corrected since no oxazolopyridines 12 hut rather arylideneimidazol-5-ones 13 are produced. In the case of pyrazolin-5-ones 14, the unavoidable formation of bis-adducts 15 always prevents any other type of reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Michael Addition versus 1,3-Cycloaddition Reactions of Pyridinium Ylides with (Arylmethylene)isoxazol-5-ones: Diastereoselective Formation of 4-[1-Aryl-2-(1-pyridinio)ethyl]isoxazolium-5-olates
  作者：Francesco Risitano、Giovanni Grassi、Giuseppe Bruno、Francesco Nicolò

  DOI：10.1002/jlac.199719970224

  日期：1997.2

  The reactions of (arylmethylene)isoxazol-5-ones 1 with pyridinium ylides 2 lead to the diastereoselective formation of olates 4. The reasons for the favored Michael addition and the unsuccessful subsequent cyclization to fused O-heterocycles are discussed on the basis of X-ray analysis as well as 1H-NMR and chemical evidences.

  （芳基亚甲基）异恶唑-5-酮1与吡啶鎓吡啶盐2的反应导致油酸酯4的非对映选择性形成。基于X射线分析以及1 H-NMR和化学证据，讨论了有利于Michael加成反应以及随后未能成功环化为稠合的O杂环的原因。