4-(4-fluoroanilino)pent-3-en-2-one | 1978-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-fluoroanilino)pent-3-en-2-one
• 英文别名: O=C(Me)CH=C(Me)N(H)(p-C6H4F)；4-(4-Fluor-anilino)-pent-3-en-2-on；2-Penten-2-ol, 4-[(4-fluorophenyl)imino]-
• CAS: 1978-63-8
• 化学式: C₁₁H₁₂FNO
• 分子量: 193.221
• InChiKey: SOYBMAFPVUEANU-UHFFFAOYSA-N

物化性质

• 沸点：
  295.0±40.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluoroanilino)pent-3-en-2-one 、 4-甲苯硫酚 在 叔丁基过氧化氢 、 copper diacetate 作用下， 以 1,4-二氧六环 、 癸烷 为溶剂， 反应 15.0h， 以65%的产率得到4-((4-fluorophenyl)amino)-3-(p-tolylthio)pent-3-en-2-one
  参考文献：
  名称：

  Copper-catalyzed direct oxidative C(sp 2 )-H α -sulfenylation of enaminones with disulfides or thiophenols: Synthesis of polyfunctionalized aminothioalkenes

  摘要：

  A copper(II)-catalyzed protocol for the construction of aminothioalkenes has been achieved that is based on the reaction of enaminones with disulfides/thiophenols in the presence of tert-butyl hydroperoxide (TBHP) to give good to excellent yields. This study provides a new strategy for the formation of C (sp(2))-S bonds via direct alpha-sulfenylation of C(sp(2))-H bonds. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.079
• 作为产物：
  描述：

  乙酰丙酮 、 4-氟苯胺 在 溶剂黄146 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以66.4%的产率得到4-(4-fluoroanilino)pent-3-en-2-one
  参考文献：
  名称：

  Solvent-Free Synthesis of N-aryl-b-Enaminones Under Microwave Irradiation

  摘要：

  在微波辐照下，乙酰丙酮与取代的苯胺发生反应，高效制备了一系列 N-芳基-b-烯丙基胺。最高收率可达 80%以上。与传统方法相比，该方法只需 15 分钟，后处理程序也更简单，但产率却更高。

  DOI：

  10.14233/ajchem.2014.15524

文献信息

• A closer look at ε-caprolactone polymerization catalyzed by alkyl aluminum complexes: the effect of induction period on overall catalytic activity
  作者：Hsi-Ching Tseng、Michael Y. Chiang、Wei-Yi Lu、Yen-Jen Chen、Cheng-Jie Lian、Yu-Hsieh Chen、Hsin-Yi Tsai、Yi-Chun Lai、Hsuan-Ying Chen

  DOI：10.1039/c5dt01563d

  日期：——

  Al complexes bearing ketimine ligands was investigated. The catalytic results indicated complexes with more steric hindrance with an electron-withdrawing group on the ligands, or the fact that less chelating ligands demonstrated greater propagation activity. The opposite trend for these structural effects was observed on the measurement of induction periods. These features on ligands of aluminum complexes

  先前对使用结构相关的铝配合物作为前催化剂的ε-己内酯的开环聚合的研究表明，总转化时间的趋势不一致。我们建议应考虑将Al络合物转化为真正的催化物质Al醇盐的诱导期，因为总转化时间包括诱导期和聚合物扩散时间。在此，研究了一系列带有酮亚胺配体的Al配合物的聚合速率。催化结果表明与配体上的吸电子基团具有更大空间位阻的配合物，或螯合配体较少的事实表明具有更大的传播活性。在诱导期的测量中观察到这些结构效应的相反趋势。铝配合物配体上的这些特征有助于促进向烷氧基铝的转化过程。总体催化性能应同时考虑诱导期和传播​​时间。
• Liquid-Assisted Mechanosynthesis of trans-2,3-Dihydropyrroles from Chalcones and Enaminones
  作者：Hui Xu、Ze Zhang、Ming-Yue Weng、Hong Chen

  DOI：10.3987/com-20-14365

  日期：——

  iodine-promoted cyclization between chalcones and enaminones has been demonstrated under liquid-assisted grinding conditions. The present protocol provides a practical, fast and green alternative to traditional solvent-based methods due to its notable advantages such as significantly higher yield, much shorter reaction time, good functional group tolerance and mild reaction conditions.

  在液体辅助研磨条件下，通过碘促进查尔酮和烯胺酮之间的环化反应，可以有效合成各种反式-2,3-二氢吡咯。由于其显着的优点，例如明显更高的收率，更短的反应时间，良好的官能团耐受性和温和的反应条件，本协议为传统的基于溶剂的方法提供了一种实用，快速且绿色的替代方法。
• Immobilization and DFT studies of Tin chloride on UiO-66 metal–organic frameworks as active catalyst for enamination of acetylacetone
  作者：Faezeh Farzaneh、Nasim Kabir、Elham Geravand、Mina Ghiasi、Mehdi Ghandi

  DOI：10.1007/s13738-019-01693-4

  日期：2019.10

  An efficient synthetic method for the preparation of β-enaminones catalyzed by immobilization of SnCl2 on Zr-metal–organic frameworks (UiO-66 MOF) and designated as SnUiO66 is described. Also the prepared catalyst was characterized by Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy (XPS), energy-dispersive X-ray spectroscopy and N2 adsorption and desorption techniques. XPS and DFT studies on Sn UiO66 were consistent with the immobilization of Sn chloride as SnIV on MOF. A variety of β-enaminones were synthesized via reaction of primary aromatic amines with acetylacetone. It was found that SnUiO66 shows moderate-to-high catalytic activity for enamination reactions. The catalyst was found to be reusable up to four catalytic cycles without any appreciable loss in activity.

  报道了一种通过将SnCl2固定在Zr-金属有机框架(UiO-66 MOF)上并命名为SnUiO66的高效β-烯胺酮合成方法。此外，制备的催化剂通过傅里叶变换红外光谱、X射线光电子光谱(XPS)、能量色散X射线光谱和氮气吸附脱附技术进行了表征。XPS和DFT对Sn UiO66的研究与Sn氯化物以SnIV形式固定在MOF上相一致。通过一级芳香胺与乙酰丙酮的反应合成了多种β-烯胺酮。研究发现，SnUiO66在烯胺化反应中表现出中等至高的催化活性。该催化剂在连续四个催化循环中可重复使用，活性几乎无损失。
• Convenient one-step synthesis of pyrrolo[3,4-c]quinolin-1-ones via TMSCl-catalyzed cascade reactions of isatins and β-enamino ketones
  作者：Hui Xu、Pan Zhou、Bei Zhou、Jie Zhou、Yuehai Shen、Ling-Ling Lu、Fu-Chao Yu

  DOI：10.1039/c6ra15492a

  日期：——

  An efficient and facile synthesis of pyrrolo[3,4-c]quinoline-1-ones by TMSCl-catalyzed reaction of easily available substituted isatins and [small beta]-enamino ketone derivatives has been developed. This cascade reaction has shown good functional group...

  已经开发了通过容易获得的取代的靛红和β-烯胺酮衍生物的TMCSC1催化的反应，可以高效且容易地合成吡咯并[3，4-c]喹啉-1-酮。该级联反应显示出良好的官能团。
• Modification of biologically active amides and amines with fluorine-containing heterocycles 1. Novel fluorine-containing heterocyclic derivatives of streptocide
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. A. Epishina、T. V. Goreva、I. V. Martynov

  DOI：10.1007/s11172-010-0061-z

  日期：2010.1

  known antimicrobial drug, streptocide, with fluorine-containing five-membered heterocycles is proposed. The reaction of the generated in situ methyl 2-[4-(N-acetylamino)phenylsulfonyl]imino-3,3,3-trifluoropropionate with 1,3-C,N- or 1,3-N,N-binucleophiles and subsequent hydrolysis of the resulting products furnished different novel fluorine-containing heterocyclic derivatives of streptocide, including fused

  提出了一种用含氟五元杂环修饰已知抗微生物药物杀链菌剂的方法。生成的 2-[4-(N-乙酰氨基) 苯基磺酰基]亚氨基-3,3,3-三氟丙酸甲酯与 1,3-C,N- 或 1,3-N,N- 亲双核试剂的原位反应以及随后的反应所得产物的水解提供了不同的新型链霉杀灭剂含氟杂环衍生物，包括稠合杂环。