(E)-ethyl 4-(4-fluorophenyl)-2-oxobut-3-enoate | 1058856-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 4-(4-fluorophenyl)-2-oxobut-3-enoate
• 英文别名: ethyl (E)-4-(4-fluorophenyl)-2-oxobut-3-enoate
• CAS: 1058856-52-2
• 化学式: C₁₂H₁₁FO₃
• 分子量: 222.216
• InChiKey: BBRNOACEHLAKPM-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(4-fluorophenyl)-2-oxobut-3-enoate 在 盐酸 、 sodium tetrahydroborate 、 ammonium acetate 、 三溴化磷 、 potassium carbonate 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 44.0h， 生成
  参考文献：
  名称：

  Highly-luminescent DTTA-appended lanthanide complexes of 4-(multi)fluoroaryl-2,2′-bipyridines: Synthesis and photophysical studies

  摘要：

  DOI：

  10.1016/j.poly.2020.114962
• 作为产物：
  描述：

  对氟苯甲醛 在 乙酰氯 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (E)-ethyl 4-(4-fluorophenyl)-2-oxobut-3-enoate
  参考文献：
  名称：

  A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid

  摘要：

  A chemo- and stereoselective 1,4-hydrosilylation of alpha,beta-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis.

  DOI：

  10.1055/s-0031-1290448

文献信息

• Facile synthesis of pyrido[3,2-b]indole via multicomponent reaction strategy under aerobic conditions
  作者：Rongrong Jiang、Youming Wang、Zhenghong Zhou

  DOI：10.1016/j.tet.2016.08.050

  日期：2016.10

  developed an organocatalyzed three-component reaction of 1-acetylindolin-3-ones, β,γ-unsaturated α-ketoesters and amines, which provide an efficient approach to access polysubstituted 1H-pyrido[3,2-b]indoles. Under the catalysis of 4-methylbenzenesulfonic acid monohydrate, the reactions of a wide range of 1-acetylindolin-3-ones, β,γ-unsaturated α-ketoesters and amines took place smoothly to generate

  我们已经开发了有机物催化的1-乙酰吲哚-3-酮，β，γ-不饱和α-酮酸酯和胺的三组分反应，这为获得多取代的1 H-吡啶并[3,2- b ]吲哚提供了一种有效的方法。在4-甲基苯磺酸一水合物的催化下，各种1-乙酰吲哚-3-酮，β，γ-不饱和α-酮酸酯和胺类的反应顺利进行，生成相应的稠密取代的1 H-吡啶基[3]。在温和的反应条件下，2-2- b ]吲哚衍生物的收率可以接受。另外，以良好的产率实现了代表性产物向生物学上重要的δ-碳卤化物的进一步转化。
• Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates
  作者：John Mansaray、Jiarui Sun、Shisheng Huang、Weijun Yao

  DOI：10.1055/s-0037-1612255

  日期：2019.4

  methods to synthesize β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates promoted by BF3•Et2O in the presence of Ac2O or by Ti(OEt)4 under mild conditions. A variety of aromatic aldehydes was tolerated to afford the desired products in moderate to excellent yield. Moreover, aliphatic aldehydes and Isatin were also employed to give the γ-alkyl β,γ-unsaturated α-keto esters in moderate yield

  在这里，我们描述了两种实用的方法，在温和条件下，在 Ac2O 或 Ti(OEt)4 存在下，由 BF3•Et2O 促进的醛和丙酮酸盐直接合成 β,γ-不饱和 α-酮酯。可以耐受各种芳香醛，以中等至极好的收率提供所需的产品。此外，脂肪醛和靛红也被用于通过使用 Ti(OEt)4 系统以中等产率得到 γ-烷基 β,γ-不饱和 α-酮酯。
• Construction of Bicyclo[3.2.1]octanes with Four Stereogenic Centers by Organocatalytic Domino Michael/Aldol Reaction
  作者：A. Lefranc、L. Gremaud、A. Alexakis

  DOI：10.1021/ol502171h

  日期：2014.10.17

  An enantio- and diastereoselective organocatalytic domino Michael/Aldol reaction for the direct preparation of synthetically and medicinally relevant bicyclo[3.2.1]octane derivatives with four stereogenic centers, including two quaternary carbons, has been described. The reaction tolerates a large variety of substituents on β,γ-unsaturated 1,2-ketoesters and cyclic 1,3-ketoesters. It allows for the

  描述了一种对映和非对映选择性的有机多米诺骨牌Michael / Aldol反应，用于直接制备具有四个立体生成中心（包括两个季碳原子）的合成和医学上相关的双环[3.2.1]辛烷衍生物。该反应可耐受β，γ-不饱和1,2-酮酸酯和环状1,3-酮酸酯上的多种取代基。它可以形成各种双环[3.2.1]辛烷，产率高（53–98％），非对映选择性（1：1至5：1 dr）和对映选择性（最高95：5 ee）。
• CuBr-Promoted Formal Hydroacylation of 1-Alkynes with Glyoxal Derivatives: An Unexpected Synthesis of 1,2-Dicarbonyl-3-enes
  作者：Shufeng Chen、Xiaojie Li、Haiying Zhao、Baoguo Li

  DOI：10.1021/jo500199v

  日期：2014.5.2

  An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with a-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.
• Metal‐Free Tandem One‐Pot Construction of 3,3‐Disubsituted 3,4‐Dihydroquinoxalin‐2(1 <i>H</i> )‐Ones under Visible‐Light Photoredox Catalysis
  作者：Zhen Yao、Zhenli Luo、Yixiao Pan、Xin Zhang、Bohan Li、Lijin Xu、Peng Wang、Qian Shi

  DOI：10.1002/adsc.202101215

  日期：2022.2

  AbstractVisible‐light photoredox‐catalyzed metal‐free tandem one‐pot synthesis of 3,3‐disubstituted 3,4‐dihydroquinoxalin‐2(1H)‐ones from easily accessible 1,2‐diaminobenzenes, α‐ketoesters and 4‐alkyl Hantzsch esters has been described. This mild transformation affords the desired products in 47–93% yields for diversely decorated substrates, and can proceed on a gram‐scale. The efficacy of the current catalysis arises from the use of organic 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as the photocatalyst and CF3CO2H as the additive.magnified image