(E)-3-苯基-1-吡啶-3-基-丙-2-烯-1-酮 | 6314-59-6

• 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: (E)-3-苯基-1-吡啶-3-基-丙-2-烯-1-酮
• 英文名称: 3-phenyl-1-(pyridin-3-yl)prop-2-en-1-one
• 英文别名: 3-phenyl-1-pyridin-3-ylprop-2-en-1-one；1-(3-pyridyl)-3-phenyl-2-propen-1-one
• CAS: 6314-59-6
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: PINRHPDVUJVFDC-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(Solv: ethanol (64-17-5))
• 沸点：
  370.0±34.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-苯基-1-吡啶-3-基-丙-2-烯-1-酮 在 Cu6(2-benzothiazolethiol(1-))6 、 potassium carbonate 、 正丁醇 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以78%的产率得到1-丙酮,3-苯基-1-(3-吡啶基)-
  参考文献：
  名称：

  使用铜（I）N供体硫代酸酯簇的不饱和羰基的可切换化学选择性转移加氢

  摘要：

  不饱和醇和饱和羰基是重要的化学，制药和生化中间体。我们在本文中报告了一种有效的转移氢化方案，其中不饱和羰基化合物转化为不饱和醇或饱和羰基的反应是由Cu（I）N供体硫醇盐簇以及变化的氢源（异丙醇或丁醇）和碱（NaOH或K）催化的。2 CO 3）。DFT过渡态建模支持的机理研究表明，这种化学选择性可以用每个催化体系中一价氢化铜（I）和质子化氢化铜（I）配合物的相对浓度来解释。

  DOI：

  10.1021/acs.joc.7b02676
• 作为产物：
  描述：

  吡啶 、 肉桂酰氯 在 zinc(II) oxide 作用下， 反应 0.15h， 以92%的产率得到(E)-3-苯基-1-吡啶-3-基-丙-2-烯-1-酮
  参考文献：
  名称：

  Zinc oxide as a regioselective and heterogeneous catalyst for the synthesis of chalcones at room temperature

  摘要：

  Zinc oxide catalyzed synthesis of chalcones has been carried out under solvent-free conditions at room temperature. Activated as well as unactivated aromatics smoothly underwent Friedel-Crafts acylation with alpha,beta-unsaturated acid chlorides furnishing excellent yields of the corresponding chalcones. The zinc oxide can be recovered and reused at least three times without any appreciable loss in activity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2012.06.012

文献信息

• Tandem vinyl radical Minisci-type annulation on pyridines: one-pot expeditious access to azaindenones
  作者：Dong Xia、Xin-Fang Duan

  DOI：10.1039/d1cc06204b

  日期：——

  A new regiospecific alkylative/alkenylative cascade annulation of pyridines has been achieved whilst the corresponding classic Minisci alkylative annulation failed. This protocol provides a novel and expeditious access to azaindenones and related compounds via cross-dehydrogenative coupling with the long-standing problem of C2/C4 regioselectivity of pyridines being well addressed.

  已经实现了吡啶的新区域特异性烷基化/烯基化级联环化，而相应的经典 Minisci 烷基化环化失败。该协议提供了一种通过交叉脱氢耦合获得氮杂茚酮和相关化合物的新型快速途径，并解决了长期存在的吡啶 C2/C4 区域选择性问题。
• Formal Diels–Alder Reactions of Chalcones and Formylcyclopropanes Catalyzed by Chiral N-Heterocyclic Carbenes
  作者：Hui Lv、Junming Mo、Xinqiang Fang、Yonggui Robin Chi

  DOI：10.1021/ol202250s

  日期：2011.10.7

  Highly enantioselective (formal) hetero-Diels–Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C–C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure

  揭示了查耳酮与甲酰基环丙烷之间的高度对映选择性（形式）杂狄尔斯-阿尔德反应。来自甲酰基环丙烷的具有挑战性的N-杂环卡宾（NHC）结合的烯酸酯中间体被捕获用于新的C-C键形成反应。获得具有高非对映异构体和对映异构体选择性的反应产物，并且可以容易地将其转化为光学纯的多取代的环己烷衍生物。
• Copper-catalyzed aerobic cascade cycloamination and acyloxylation: a direct approach to 4-acyloxy-1H-pyrazoles
  作者：Zhengwei Ding、Qitao Tan、Mingchun Gao、Bin Xu

  DOI：10.1039/c5ob00409h

  日期：——

  An efficient copper-catalyzed regioselective olefinic C(sp²)–H bond cycloamination and acyloxylation was developed to give acyloxylated pyrazoles under mild conditions, which combines the formation of the pyrazole skeleton and installation of an acyloxyl group in a single step.

  一种高效的铜催化的选择性合成烯烃C(sp2)-H键环胺化和酰氧化反应被开发出来，在温和条件下得到了酰氧化吡唑化合物，该方法将吡唑骨架的形成和酰氧基团的引入结合在一个步骤中。
• A regioselective and convenient one-pot multicomponent synthesis of 9-amino-3,5-diaryl-4,9-dihydro-5<i>H</i>-[1,2,4]triazolo[5,1-<i>c</i>][1,2,4]triazepine-8-thiol
  作者：Amr Hassan Moustafa、Amer Anwar Amer

  DOI：10.1080/00397911.2017.1314494

  日期：2017.6.3

  environment-friendly procedure for the synthesis of a new series of nitrogen bridge-head [1,2,4]triazolo[5,1-c][1,2,4]triazepine derivatives through one-pot three-component reaction of polyfunctional triazole with aromatic aldehydes and acetophenone derivatives using alcoholic sodium hydroxide solution. The same new products were prepared in classical route through reaction of triazole with the corresponding chalcones

  摘要 一种高效、环保的新型氮桥头[1,2,4]三唑并[5,1-c][1,2,4]三氮杂衍生物一锅三氮合成方法多官能三唑与芳香醛和苯乙酮衍生物在氢氧化钠醇溶液中的组分反应。在相同条件下，通过三唑与相应的查耳酮反应，以经典路线制备相同的新产品。图形概要
• EGFR/HER-2 inhibitors: synthesis, biological evaluation and 3D-QSAR analysis of dihydropyridine-containing thiazolinone derivatives
  作者：Yu-Jia Ren、Zhong-Chang Wang、Xin Zhang、Han-Yue Qiu、Peng-Fei Wang、Hai-Bin Gong、Ai-Qin Jiang、Hai-Liang Zhu

  DOI：10.1039/c4ra10606g

  日期：——

  A series of dihydropyridin containing thiazolinone derivatives (4a–4r) have been designed, synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors and tumor cell antiproliferation.

  一系列含有噻唑酮衍生物的二氢吡啶衍生物（4a-4r）已经设计、合成，并评估了它们作为潜在的EGFR和HER-2激酶抑制剂以及肿瘤细胞抗增殖活性。