4-(4-bromophenylamino)-3-penten-2-one | 62070-33-1

• 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-bromophenylamino)-3-penten-2-one
• 英文别名: 4-(4-bromophenylamino)pent-3-en-2-one；4-(4-Bromoanilino)pent-3-en-2-one
• CAS: 62070-33-1
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: KYJFBKPPRYRZLS-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  342.6±42.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenylamino)-3-penten-2-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.6h， 生成 3-acetyl-1-(4-bromophenyl)-2-methyl-4-oxa-1-azacyclopenta[a]naphthalen-5-one
  参考文献：
  名称：

  Facile synthesis of substituted pyrrole-fused isocoumarins from ninhydrin

  摘要：

  A simple and efficient procedure has been developed for the synthesis of substituted pyrrole-fused isocoumarins from easily available ninhydrin. The cyclic hemiaminal dihydroxy-indenopyrroles, the adducts of ninhydrin with enamines of acetylacetone, give pyrrole-fused isocournarins upon heating in acidic medium. The process constitutes an interesting acid-catalyzed rearrangement to eight-membered lactams followed by intramolecular cyclization involving the amino and keto groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.133
• 作为产物：
  描述：

  乙酰丙酮 、 4-溴苯胺 以 neat (no solvent) 为溶剂， 反应 1.5h， 以41%的产率得到4-(4-bromophenylamino)-3-penten-2-one
  参考文献：
  名称：

  具有β-酮化辅助配体的可电聚合IrIII配合物。

  摘要：

  合成了一系列可电聚合的环金属化的IrIII配合物，并研究了它们的电化学和光物理性质。通过使用三苯胺-2-苯基吡啶和三苯胺-苯并噻唑分别作为环金属化的配体引入三苯胺可电聚合的片段。配位球由两个不同取代的β-酮亚胺基配位体完成，这些配体来自乙酰丙酮或六氟乙酰丙酮与对溴苯胺的缩合。研究了-CH 3 / -CF 3取代对电化学和光物理性质的影响。具有CH 3取代的β-酮亚胺的两种络合物在溶液和固态下均能发光。将高度稳定的薄膜电沉积到ITO涂覆的玻璃基板上。如电化学研究所证实的那样，它们的发射通过聚合物网络中的电子俘获来淬灭。β-酮亚胺基的-CF3取代反而导致了发射的猝灭并抑制了电聚合。

  DOI：

  10.1002/asia.201900521

文献信息

• 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。
• β-Enaminones over recyclable nano-CoFe2O4: a highly efficient solvent-free green protocol
  作者：Esmaiel Eidi、Mohamad Z. Kassaee、Peter T. Cummings

  DOI：10.1007/s11164-018-3454-5

  日期：2018.10

  Abstract β-Enaminone and its derivatives have emerged among the finest bioactive intermediates. High yields of several β-enaminones (86–97%) are achieved through treatment of substituted aromatic and aliphatic amines with cyclic/acyclic 1,3-diketones, over the magnetically separable cobalt ferrite nanoparticles (CoFe2O4 NPs). The latter was prepared upon co-precipitation. Its purity, fine crystallinity

  摘要 β-烯胺酮及其衍生物已经出现在最好的生物活性中间体中。通过在磁性可分离的钴铁氧体纳米粒子（CoFe 2 O 4 NPs）上用环状/无环的1,3-二酮处理取代的芳香族和脂肪族胺，可以实现几种β-烯酮的高收率（86-97％）。后者是在共沉淀条件下制备的。通过傅立叶变换红外光谱，X射线衍射，能量色散X射线光谱法，扫描电子显微镜，振动样品磁法和热重分析分析，确认了其纯度，精细的结晶度，元素分布，形态，磁性和热稳定性。因此，CoFe 2 O 4NPs是合成β-烯胺酮的优良绿色异质纳米催化剂，具有良好的可回收性，但其活性却微不足道。 图形概要
• A novel and reusable magnetic nanocatalyst developed based on graphene oxide incorporated strontium nanoparticles for the facial synthesis of β-enamino ketones under solvent-free conditions
  作者：Seyyed Rasul Mousavi、Hassan Sereshti、Hamid Rashidi Nodeh、Alireza Foroumadi

  DOI：10.1002/aoc.4644

  日期：2019.1

  A novel magnetic SrFeGO nanocatalyst (NC) was synthesized through a simple sol–gel technique by introducing strontium and iron oxide nanoparticles onto graphene. The synthesized NC was characterized using FT‐IR and FE‐SEM. Subsequently, the catalytic activity of SrFeGO was tested in a reaction between β‐dicarbonyl compounds and aniline derivatives to gain β‐enamino ketone derivatives under solvent‐free

  通过将锶和氧化铁纳米颗粒引入石墨烯，通过简单的溶胶-凝胶技术合成了一种新型的磁性SrFeGO纳米催化剂（NC）。使用FT-IR和FE-SEM对合成的NC进行表征。随后，在无溶剂条件下，在β-二羰基化合物与苯胺衍生物之间的反应中测试了SrFeGO的催化活性，以获得β-烯氨基酮衍生物。发现SrFeGO NC是合成β-烯胺酮的潜在催化剂。通过这种反应产生的β-烯氨基酮可以无需色谱纯化就可以高纯度分离。新制备的磁性氧化石墨烯纳米复合材料可以回收并重复使用多次，而效率没有明显降低。此外，
• 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。
• A Highly Diastereoselective Three-component Domino Reaction in Water Yielding Poly-substituted 4,5-Dihydropyrroles
  作者：Guangjing Tong、Haiwei Xu、Wei Fan、Bo Jiang、Shuliang Wang、Shujiang Tu

  DOI：10.1002/cjoc.201300249

  日期：2013.8

  synthesis of poly‐substituted 4,5‐dihydropyrrole derivatives from readily available common reactants in water has been developed. During domino processes, the formation of pyrrole skeleton and its C2‐hydroxylation and C3‐arylamination were readily achieved via metal‐free [3+2] heterocyclization in a one‐pot operation.

  已经开发了一种有效的方法，用于从水中易得的常见反应物中高度非对映选择性地合成多取代的4,5-二氢吡咯衍生物。在多米诺骨牌过程中，吡咯骨架的形成及其C2羟基化和C3芳基化很容易通过无金属的[3 + 2]杂环化反应在一个锅中完成。