3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one oxime | 5351-37-1

• 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: 3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one oxime
• 英文别名: Chalcone oxime；3-(4-methoxy-phenyl)-1-phenyl-propenone oxime；(p-Methoxy-benzyliden)-acetophenon-oxim；4-Methoxychalconoxim；N-[3-(4-methoxyphenyl)-1-phenylprop-2-enylidene]hydroxylamine
• CAS: 5351-37-1
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: TXOGAKDQSWGTTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one oxime 在 cobalt(II) acetate 氧气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-(4-methoxy-phenyl)-3-phenyl-4,5-dihydro-isoxazol-4-ol
  参考文献：
  名称：

  Kikuchi,K. et al., Heterocycles, 1978, vol. 11, p. 187 - 190

  摘要：

  DOI：

文献信息

• Iron(<scp>iii</scp>)-catalyzed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from <i>N</i>-vinyl-α,β-unsaturated ketonitrones
  作者：Chun-Hua Chen、Qing-Yan Wu、Cui Wei、Cui Liang、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1039/c8gc00630j

  日期：——

  An iron(III)-catalyst controlled cyclization and selective N–O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines

  在温和的条件下，以中等至良好的产率获得四取代吡啶和3,5-二取代异恶唑啉，已实现铁（III）催化剂控制的环化和N-乙烯基-α，β-不饱和硝酮的选择性N–O键裂解。用FeCl 3作为催化剂提供四取代的吡啶，同时使用FeCl 3 ·6H 2 O与1,10-菲咯啉传递的异恶唑啉组合。N中苯乙烯基环化的区域选择性吡啶和异恶唑啉的形成过程中，-乙烯基-α，β-不饱和硝酮完全不同。在进一步的对照实验研究的基础上，提出了形成吡啶和异恶唑啉的合理机理。当将乙酸铜（II）与制备的双齿N-配体结合使用时，可将异恶唑啉经四个步骤转化为新的双齿N-配体，并且从N-乙烯基硝酮获得环氧吡啶骨架。
• Formal [7 + 2] Cycloaddition of Arynes with <i>N</i>-Vinyl-α,β-Unsaturated Nitrones: Synthesis of Benzoxazonines and Their N–O Bond Cleavage
  作者：Xiao-Pan Ma、Liang-Gui Li、Hong-Ping Zhao、Min Du、Cui Liang、Dong-Liang Mo

  DOI：10.1021/acs.orglett.8b01761

  日期：2018.8.3

  N-vinyl-α,β-unsaturated nitrones under mild conditions. Controllable N–O bond cleavage of benzoxazonines afforded polysubstituted pyrrole-tethered benzopyrans and acyclic ketone-substituted phenols in moderate to good yields. Further transformations provided a facile approach to access useful building blocks with specific stereoselectivity.

  在温和的条件下，通过芳烃与N-乙烯基-α，β-不饱和硝酮的正式[7 + 2]环加成反应，合成了各种苯并恶唑啉。苯并恶唑酮的可控N–O键裂解提供了中等至良好的收率的多取代吡咯系苯并吡喃和无环酮取代的苯酚。进一步的转换提供了一种简便的方法来访问具有特定立体选择性的有用构建基块。
• Synthesis of 3,5-diarylisoxazoles under solvent-free conditions using iodobenzene diacetate
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Thripuraribhatla Venkata Naga Varun Sasank、Hunsur Nagendra Nagesh、Narva Suresh、Kalaga Mahalakshmi Naidu、Amaroju Suresh

  DOI：10.1016/j.cclet.2013.07.022

  日期：2013.12

  Abstract A simple and efficient method has been developed for conversion of chalcone oximes to 3,5-diaryl isoxazoles in excellent yields under solvent-free conditions. The synthesized compounds were characterized by infrared spectroscopy, 1 H NMR, 13 C NMR and HRMS.

  摘要研究了一种简单有效的方法，可在无溶剂条件下以优异的收率将查尔酮肟转化为3,5-二芳基异恶唑。合成的化合物通过红外光谱，1 H NMR，13 C NMR和HRMS进行表征。
• Synthesis of α,β-Unsaturated <i>N</i>-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free <i>N</i>-Arylation Process
  作者：Xiao-Pan Ma、Wei-Min Shi、Xue-Ling Mo、Xiao-Hua Li、Liang-Gui Li、Cheng-Xue Pan、Bo Chen、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.5b01716

  日期：2015.10.16

  An efficient transition-metal-free method for the preparation of alpha,beta-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.
• Sharma, T. C.; Rojindar, S.; Berge, D. D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 437
  作者：Sharma, T. C.、Rojindar, S.、Berge, D. D.、Kale, A. V.

  DOI：——

  日期：——