(Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one | 36298-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one
• 英文别名: (4Z)-4-[(4-methoxyphenyl)methylidene]-3-phenyl-1,2-oxazol-5-one
• CAS: 36298-62-1
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: HGIIHVJCDPYWBJ-PTNGSMBKSA-N

物化性质

• 溶解度：
  39.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one 以 甲醇 、 甲苯 为溶剂， 反应 0.25h， 生成 4-(4-methoxyphenyl)-1-methyl-2,5-diphenylpyrrole-3-carboxylic acid
  参考文献：
  名称：

  Clerici, Francesca; Erba, Emanuela; Mornatti, Pierluigi, Chemische Berichte, 1989, vol. 122, p. 295 - 300

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-methoxybenzaldehyde O-3-phenylpropioloyl oxime 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以88%的产率得到(Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one
  参考文献：
  名称：

  Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of O-Propioloyl Oximes

  摘要：

  Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 degrees C in the presence of Au(PPh(3))NTf(2) (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.

  DOI：

  10.1021/ol100581m

文献信息

• Sequential 5(4H)-Oxazolone Cycloaddition and Nitrile Oxide Addition Reactions with 4-Arylmethyleneisoxazol-5-ones: Regioselective Synthesis of N-Unsubstituted Pyrrole Hydroxamate Derivatives
  作者：Giovanni Grassi、Francesco Risitano、Francesco Foti、Massimiliano Cordaro

  DOI：10.1055/s-2001-14604

  日期：——

  The regioselective synthesis of N-unsubstituted pyrrol-3-yl hydroxamates starting from (Z)-4-arylmethyleneisoxazol-5-ones may be readily achieved by the use of sequential 5(4H)-oxazolone cycloaddition and nitrile oxide addition reactions.

  以（Z）-4-芳亚甲基异噁唑啉-5-酮为原料，通过连续的5（4H）-异噁唉酮环加成和腈氧化物加成反应，可以容易地实现N-未取代的吡咯-3-基羟肟酸的选择性合成。
• 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。
• Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4<i>H</i>)‐one Derivatives and Isocyanoacetate Esters
  作者：Pablo Martínez‐Pardo、Adrián Laviós、Amparo Sanz‐Marco、Carlos Vila、José R. Pedro、Gonzalo Blay

  DOI：10.1002/adsc.202000611

  日期：2020.9.8

  spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4‐arylideneisoxazol‐5‐ones and isocyanoacetate esters using a bifunctional squaramide/Brønsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method

  通过协同系统催化的正式的[3 + 2]环加成反应，获得了具有三个连续立体中心和高官能度的对映体富集的螺环化合物。使用由金鸡纳生物碱和氧化银（路易斯酸）衍生的双官能方胺/布朗斯台德碱有机催化剂，由4-芳叉基异恶唑5-1和异氰基乙酸酯合成螺化合物。该方法提供了四种可能的非对映异构体中的两种，具有良好的收率和两种非对映异构体的高对映体过量。
• 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。
• 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。