(E)-ethyl 4-(3-chlorophenyl)-2-oxobut-3-enoate | 1058856-54-4

• 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-(3-chlorophenyl)-2-oxobut-3-enoate
• 英文别名: ethyl (E)-4-(3-chlorophenyl)-2-oxobut-3-enoate
• CAS: 1058856-54-4
• 化学式: C₁₂H₁₁ClO₃
• 分子量: 238.671
• InChiKey: FWHLKJYTADRIPV-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(3-chlorophenyl)-2-oxobut-3-enoate 在 盐酸 、 [NH2Me2]+[{RuCl[(S)-SunPhos]}2(μ-Cl3)] 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 70.0 ℃ 、1.4 MPa 条件下， 反应 12.0h， 生成 ethyl (S)-4-(3-chlorophenyl)-2-hydroxybutanoate
  参考文献：
  名称：

  Highly Enantioselective Sequential Hydrogenation of Ethyl 2-Oxo-4-arylbut-3-enoate to Ethyl 2-Hydroxy-4-arylbutyrate

  摘要：

  The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2](+)[{RuCl [(S)-SunPhos]}2(mu-Cl-3] gave ethyl 2-hydroxy-4-arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C = O and C = C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81 % yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.

  DOI：

  10.1021/jo801140j
• 作为产物：
  描述：

  3-氯苯甲醛 在 乙酰氯 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (E)-ethyl 4-(3-chlorophenyl)-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。
• A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid
  作者：Biao Jiang、Ping Xing、Wei Zang、Zuo-gang Huang、Yue-xiong Zhan、Chuan-jun Zhu

  DOI：10.1055/s-0031-1290448

  日期：——

  A chemo- and stereoselective 1,4-hydrosilylation of alpha,beta-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis.
• Highly Enantioselective Sequential Hydrogenation of Ethyl 2-Oxo-4-arylbut-3-enoate to Ethyl 2-Hydroxy-4-arylbutyrate
  作者：Qinghua Meng、Lufeng Zhu、Zhaoguo Zhang

  DOI：10.1021/jo801140j

  日期：2008.9.19

  The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2](+)[RuCl [(S)-SunPhos]}2(mu-Cl-3] gave ethyl 2-hydroxy-4-arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C = O and C = C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81 % yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.