1,5-二苯基-2,4-戊二烯-1-酮肟 | 146537-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二苯基-2,4-戊二烯-1-酮肟
• 英文名称: 1,5-diphenyl-2,4-pentadien-1-one oxime
• 英文别名: 1,5-diphenyl-penta-2,4-dien-1-one oxime；1,5-Diphenyl-penta-2,4-dien-1-on-oxim；N-(1,5-diphenylpenta-2,4-dienylidene)hydroxylamine
• CAS: 146537-63-5
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: GTSKLTUOZBOQHK-UHFFFAOYSA-N

物化性质

• 沸点：
  429.9±28.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-二苯基-2,4-戊二烯-1-酮肟 在 氢氧化钾 、 亚硝酸丁酯 、 copper(II) sulfate 作用下， 生成 3(5)-phenyl-5(3)-styryl-1-hydroxypyrazole 2-oxide
  参考文献：
  名称：

  Alkenyl-substituted N,N''-Dioxygenated Pyrazoles by Nitrosation of Dienone Oximes

  摘要：

  DOI：

  10.3987/com-98-8341
• 作为产物：
  描述：

  肉桂醛 在 sodium hydroxide 、 乙醇 、 盐酸羟胺 作用下， 生成 1,5-二苯基-2,4-戊二烯-1-酮肟
  参考文献：
  名称：

  Scholtz, Chemische Berichte, 1895, vol. 28, p. 1726

  摘要：

  DOI：

文献信息

• Solvent-Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles
  作者：Dong-Liang Mo、Donald J. Wink、Laura L. Anderson

  DOI：10.1002/chem.201403268

  日期：2014.10.6

  A solvent‐controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N‐aryl‐α,β‐unsaturated nitrones and electron‐deficient allene starting materials. These reactions proceed smoothly under mild metal‐free conditions affording a range of two types of skeletally distinct indole‐based heterocycles in high yield

  已经确定了一种溶剂控制的级联工艺，可用于从相同的N-芳基-α，β-不饱和硝酮和缺电子的丙二烯起始原料制备二氢咔唑或二氢吡啶并吲哚的双重目的。这些反应在无金属的温和条件下可以顺利进行，从而提供了两种类型的骨架不同的吲哚基杂环化合物，具有高收率和非对映选择性。这些转化表明使用了分叉的级联过程，该过程取决于苯并ze庚因中间体的开环事件，以合成骨架多样的杂环产物，并快速获得具有生物学意义的，基于吲哚的结构。
• Copper-catalyzed aerobic oxidative C–O bond formation for the synthesis of 3,5-disubstituted isoxazoles from enone oximes
  作者：Yadong Sun、Ablimit Abdukader、Haiyan Zhang、Wanle Yang、Chenjiang Liu

  DOI：10.1039/c7ra11436b

  日期：——

  oxidative coupling reaction of enone oximes using a catalytic quantity of Cu(OAc)2. This method features an inexpensive metal catalyst, molecular oxygen as a green oxidant, good functional group tolerance and readily available starting materials. This attractive method for the synthesis of isoxazole derivatives is of great significance due to the product's versatile reactivity for further transformations.

  通过使用催化量的Cu（OAc）2的烯酮肟的分子内氧化偶联反应，可以直接获得3,5-二取代的异恶唑。该方法的特点是廉价的金属催化剂，分子氧作为绿色氧化剂，良好的官能团耐受性和易于获得的起始原料。合成异恶唑衍生物的这一有吸引力的方法具有重要意义，因为该产品对进一步转化具有广泛的反应性。
• Kohler, American Chemical Journal, 1907, vol. 38, p. 559
  作者：Kohler

  DOI：——

  日期：——
• TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles
  作者：Ablimit Abdukader、Yadong Sun、Zengpeng Zhang、Chenjiang Liu

  DOI：10.1016/j.catcom.2017.11.008

  日期：2018.2

  A TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles was developed, providing 3,5-diarylisoxazoles in good yields. Functional groups such as methoxy, ethyoxyl, chloro, bromo, fluoro and nitro were well tolerated in this reaction. Notably, the reaction ran under metal-free in water.
• Synthesis of <i>N</i>-Styrenyl Amidines from α,β-Unsaturated Nitrones and Isocyanates through CO₂ Elimination and Styrenyl Migration
  作者：Dong-Liang Mo、Wiktoria H. Pecak、Meng Zhao、Donald J. Wink、Laura L. Anderson

  DOI：10.1021/ol501503a

  日期：2014.7.18

  A mild, metal-free, and modular route for the preparation of N-styrenyl amidines from N-aryl-alpha,beta-unsaturated nitrones and isocyanates has been developed that accesses an initial oxadiazolidinone intermediate that can undergo CO2 elimination and styrenyl migration. The use of a migration event to install N-styrenyl amidine substituents circumvents a limitation of traditional Pinner-type methods for amidine synthesis that require the use of amine nucleophiles. The modularity of the nitrone and isocyanate reagents provides access to a variety of differentially substituted N-styrenyl amidines. The scope and tolerance of the method are presented, and preliminary mechanistic data for the transformation are discussed.