(Z)-3-phenyl-4-(2,4,6-trimethylbenzylidene)isoxazol-5(4H)-one | 89114-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (Z)-3-phenyl-4-(2,4,6-trimethylbenzylidene)isoxazol-5(4H)-one
• 英文别名: 4-(2,4,6-trimethylphenyl)methylene-3-phenylisoxazol-5-one；3-phenyl-4-(2,4,6-trimethyl-benzylidene)-4H-isoxazol-5-one；Z-3-Phenyl-4-(2,4,6-trimethylbenzyliden-isoxazolin-5-on；3-Phenyl-4-(2,4,6-trimethylbenzylidene)isoxazol-5(4H)-one；(4Z)-3-phenyl-4-[(2,4,6-trimethylphenyl)methylidene]-1,2-oxazol-5-one
• CAS: 89114-08-9
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: JCCAOHVUEXIFQM-BOPFTXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-phenyl-4-(2,4,6-trimethylbenzylidene)isoxazol-5(4H)-one 在 2,4,6-三甲基苯甲醛 、 邻苯二胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到3-phenyl-4-[(2,4,6-trimethylphenyl)methyl]-4H-1,2-oxazol-5-one
  参考文献：
  名称：

  由4-芳基亚甲基吡唑-5-酮和异恶唑-5-酮与2-芳基苯并咪唑啉的C，C-和C，N-连接的二聚体和4-芳基甲基衍生物。

  摘要：

  由邻苯二胺（7）和适当的芳醛通过与4-芳基亚甲基吡唑-5-酮（1）或异恶唑-5-酮（2）反应原位生成的2-芳基苯并咪唑啉（8），生成4-芳基甲基衍生物（3）或（4）和C，C-（5）或C，N-连接的二聚体。基于2-芳基苯并咪唑啉作为还原剂的作用使反应合理化，并通过涉及单电子转移的非链自由基过程进行反应。

  DOI：

  10.1016/0040-4020(95)00970-1
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 4-(3-Oxo-1,3-diphenyl-2-pyridin-1-ium-1-ylpropyl)-3-phenyl-1,2-oxazol-5-olate 在 乙酸铵 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 (Z)-3-phenyl-4-(2,4,6-trimethylbenzylidene)isoxazol-5(4H)-one 、 (9E)-9-benzylidene-4,6,8-triphenyl-2-oxa-3,7-diazaspiro[4.4]nona-3,7-dien-1-one
  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

• 4-Arylmethylisoxazol-5-one Derivatives − Novel Synthesis, Structural Studies, and Supramolecular Self-Assembly through Resonance-Assisted Hydrogen Bonding
  作者：Giovanni Grassi、Giuseppe Bruno、Francesco Risitano、Francesco Foti、Francesco Caruso、Francesco Nicolò

  DOI：10.1002/1099-0690(200112)2001:24<4671::aid-ejoc4671>3.0.co;2-z

  日期：2001.12

  derivatives are reported and are shown to have the expected different tautomeric arrangements. The unusual features of the NH-tautomer (3e) were interpreted in terms of the RAHB (resonance-assisted hydrogen bond) model and its relative stability was investigated by ab initio and DFT calculations.

  通过新的温和的还原程序，使用含有柔性N-CH-CH基团的叔胺，通过新的温和的还原程序制备了芳基甲基异恶唑-5-酮（3）。并发工艺与还原竞争，产生了相当数量的链延伸产物（4）。报告了两种选择的芳基甲基衍生物的X射线结构，并显示具有预期的不同互变异构排列。用RAHB（共振辅助氢键）模型解释了NH-互变异构体（3e）的不寻常特征，并通过从头算和DFT计算研究了其相对稳定性。
• An efficient preparation of 4-arylmethylisoxazol-5-ones by selective reduction of the 4-arylmethyleneisoxazol-5-ones
  作者：Francesco Risitano、Giovanni Grassi、Francesco Foti

  DOI：10.1016/s0040-4039(00)94230-8

  日期：1983.1
• RISITANO, F.;GRASSI, G.;FOTI, F., TETRAHEDRON LETT., 1983, 24, N 52, 5893-5896
  作者：RISITANO, F.、GRASSI, G.、FOTI, F.

  DOI：——

  日期：——
• C,C- and C,N-linked dimers and 4-arylmethyl derivatives from 4-arylmethylene pyrazol-5-ones and isoxazol-5-ones with 2-arylbenzim idazolines.
  作者：Francesco Risitano、Giovanni Grassi、Francesco Caruso、Francesco Foti

  DOI：10.1016/0040-4020(95)00970-1

  日期：1996.1

  2-arylbenzimidazolines (8), generated in situ from o-phenylenediamine (7) and the appropriate arylaldehydes, by reaction with 4-arylmethylene pyrazol-5-ones (1) or isoxazol-5-ones (2) produce the 4-arylmethyl derivatives (3) or (4) and the C,C- (5) or the C,N-linked dimers. The reaction was rationalised on the basis of the role of 2-arylbenzimidazoline as a reducing agent and proceeds by a non-chain

  由邻苯二胺（7）和适当的芳醛通过与4-芳基亚甲基吡唑-5-酮（1）或异恶唑-5-酮（2）反应原位生成的2-芳基苯并咪唑啉（8），生成4-芳基甲基衍生物（3）或（4）和C，C-（5）或C，N-连接的二聚体。基于2-芳基苯并咪唑啉作为还原剂的作用使反应合理化，并通过涉及单电子转移的非链自由基过程进行反应。
• 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.