(3E)-4-(4-chlorophenyl)-2-oxobut-3-enoic acid ethyl ester | 145784-33-4

• 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: (3E)-4-(4-chlorophenyl)-2-oxobut-3-enoic acid ethyl ester
• 英文别名: (E)-4-(4-chlorophenyl)-2-oxo-3-butenoic acid ethyl ester；4-(4-chlorophenyl)-2-oxo-but-3-enoic acid ethyl ester；(E)-ethyl 4-(4'-chlorophenyl)-2-oxo-3-butenoate；(E)-ethyl 4-(4-chlorophenyl)-2-oxobut-3-enoate；ethyl (E)-4-(4-chlorophenyl)-2-oxobut-3-enoate；ethyl 4-(4-chlorophenyl)-2-oxo-3-butenoate
• CAS: 145784-33-4
• 化学式: C₁₂H₁₁ClO₃
• 分子量: 238.671
• InChiKey: UGAAYCHCCALRHV-VMPITWQZSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  355.2±34.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

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：

  (3E)-4-(4-chlorophenyl)-2-oxobut-3-enoic acid ethyl ester 在 Candida parapsilosis ATCC 7330 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以59%的产率得到ethyl (E,2S)-4-(4-chlorophenyl)-2-hydroxybut-3-enoate
  参考文献：
  名称：

  Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and -but-3-enoates by Candida parapsilosis ATCC 7330: assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR

  摘要：

  Enantioselective bioreduction of alkyl 2-oxo-4-arylbutanoates and 2-oxo-4-arylbut-3-enoates mediated by Candida parapsilosis ATCC 7330 resulted in the formation of the corresponding (S)-2-hydroxy compounds in high enantiomeric excesses (93-99%) and good isolated yields (58-71%). The absolute configuration of enantiomerically pure ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate obtained by the reduction of the corresponding keto ester was assigned by H-1 NMR using Mosher's method. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.002
• 作为产物：
  描述：

  4-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 (3E)-4-(4-chlorophenyl)-2-oxobut-3-enoic acid ethyl ester
  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

• Skraup−Doebner−Von Miller Quinoline Synthesis Revisited:  Reversal of the Regiochemistry for γ-Aryl-β,γ-unsaturated α-Ketoesters
  作者：Yan-Chao Wu、Li Liu、Hui-Jing Li、Dong Wang、Yong-Jun Chen

  DOI：10.1021/jo060290n

  日期：2006.8.1

  A reversal of the standard regiochemistry of the Skraup−Doebner−Von Miller quinoline synthesis was observed when anilines were condensed with γ-aryl-β,γ-unsaturated α-ketoesters in refluxing TFA. The reaction is proposed to involve 1,2-addition of the anilines to γ-aryl-β,γ-unsaturated α-ketoesters to form Schiff's base adducts, followed by cyclization and oxidation. The products were unambiguously

  当苯胺与回流的TFA中的γ-芳基-β，γ-不饱和α-酮酸酯缩合时，观察到了Skraup-Doebner-Von Miller喹啉合成的标准区域化学的逆转。建议该反应包括将苯胺1，2-加成到γ-芳基-β，γ-不饱和的α-酮酸酯上，形成席夫碱加合物，然后环化和氧化。通过光谱法和X射线晶体学分析将产物明确显示为2-羧基-4-芳基喹啉。
• A New Synthetic Method for α-Oxo-β,γ-unsaturated Esters
  作者：Hideyuki Sugimura、Kazuhiro Yoshida

  DOI：10.1246/bcsj.65.3209

  日期：1992.11

  α-Oxo-β,γ-unsaturated esters have been prepared in moderate to good yields via a two-step procedure consisting of the boron trifluoride-promoted reaction of 2-(trimethylsiloxy)acrylic esters with acetals, followed by treatment with silica gel in benzene under reflux.

  α-氧代-β,γ-不饱和酯已通过两步法以中等至良好的产率制备，该方法包括先用三氟化硼促进2-(三甲基硅氧基)丙烯酸酯与缩醛的反应，然后在回流苯中用硅胶处理。
• 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。
• Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Vinyl Cyclopropanes and β,γ-Unsaturated α-Keto Esters: An Effective Route to Highly Functionalized Cyclopentanes
  作者：Liang-yong Mei、Yin Wei、Qin Xu、Min Shi

  DOI：10.1021/om300896z

  日期：2012.11.12

  Palladium-catalyzed asymmetric formal [3+2] cycloaddition of vinyl cyclopropanes and β,γ-unsaturated α-keto esters proceeded smoothly in the presence of chiral imidazoline–phosphine ligands to give the corresponding highly functionalized cyclopentanes in good yields along with high diastereo- and enantioselectivities under mild conditions.

  在手性咪唑啉-膦配体的存在下，钯催化的乙烯基环丙烷和β，γ-不饱和α-酮酯的不对称形式[3 + 2]环加成反应顺利进行，从而得到相应的高度官能化的环戊烷，并具有较高的非对映体-收率。和温和条件下的对映选择性。
• Rapid Access to Benzoxaphospholes and Their Spiro Analogues by a Three-Component Coupling Involving Arynes, Phosphines, and Activated Ketones
  作者：Anup Bhunia、Tony Roy、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/ol502490t

  日期：2014.10.3

  multicomponent coupling involving in situ generated arynes from 2-(trimethylsilyl)aryl triflates, phosphines, and various acyclic and cyclic activated carbonyl compounds has been developed. The reaction proceeds via a formal [3 + 2] cycloaddition mode giving access to differently substituted (spiro)benzoxaphosphole derivatives in moderate to good yields. Mild reaction conditions, a broad scope, and the possibility

  已开发出一种操作简单的多组分偶联方法，涉及从2-（三甲基甲硅烷基）芳基三氟甲磺酸酯，膦和各种无环和环状活化羰基化合物中原位生成的芳烃。反应通过正式的[3 + 2]环加成反应模式进行，从而可以中等至良好的产率获得不同取代的（螺）苯并恶唑衍生物。温和的反应条件，广泛的范围以及改变所有三个组分的可能性是本反应的显着特征。