(E)-ethyl 4-(3-bromophenyl)-2-oxobut-3-enoate | 1160761-51-2

• 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-(3-bromophenyl)-2-oxobut-3-enoate
• 英文别名: ethyl (E)-4-(3-bromophenyl)-2-oxobut-3-enoate
• CAS: 1160761-51-2
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: XZWRTWNTPLDTEM-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-bromophenyl)-2-oxobut-3-enoate 、 偶氮二甲酸二乙酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到triethyl 5-(3-bromophenyl)-1H-pyrazole-1,2,3(5H)-tricarboxylate
  参考文献：
  名称：

  通过膦促进的偶氮二羧酸二烷基酯与 β,γ-不饱和 α-酮酯的 [2 + 3] 环加成制备吡唑啉衍生物的简便策略

  摘要：

  摘要开发了一种简便的膦促进的偶氮二羧酸二烷基酯与β,γ-不饱和α-酮酯的[2+3]环加成反应，并在温和的条件下以良好的收率获得了一系列吡唑啉衍生物。此外，还研究了环化的范围。图形概要

  DOI：

  10.1080/00397911.2018.1435819
• 作为产物：
  描述：

  间溴苯甲醛 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-bromophenyl)-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

• NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides
  作者：Stuart M. Leckie、T. Bruce Brown、David Pryde、Tomas Lebl、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1039/c3ob40424b

  日期：——

  Chiral N-heterocyclic carbenes (NHCs) promote the asymmetric formal [4 + 2] cycloaddition of alkylarylketenes with β,γ-unsaturated α-ketocarboxylic esters and amides. Divergent diastereoselectivity is observed in this process, with γ-aryl-β,γ-unsaturated α-ketocarboxylic esters and amides giving preferentially syn-dihydropyranones (up to 68 : 32 dr syn : anti, up to 98% ee), while γ-alkyl-derivatives generate

  手性N-杂环卡宾（NHC）促进烷基芳基烯酮与β，γ-不饱和α-酮羧酸酯和酰胺的不对称形式[4 + 2]环加成。在此过程中观察到不同的非对映选择性，其中γ-芳基-β，γ-不饱和α-酮羧酸酯和酰胺优先提供顺-二氢吡喃酮（高达68:32 dr syn  ：  anti，高达98％ee），而γ-烷基衍生物生成抗二氢吡喃酮（高达18:82 dr syn  ：  anti，高达75％ee）。
• DABCO-catalyzed regioselective cyclization reactions of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters
  作者：Cheng-Kui Pei、Lei Wu、Zhong Lian、Min Shi

  DOI：10.1039/c1ob06507f

  日期：——

  Highly efficient DABCO-catalyzed [4 + 2] cycloaddition of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters gives the corresponding highly functionalized tetrahydropyran and dihydropyran derivatives in good to excellent yields and moderate to good regioselectivities under mild conditions.

  高效的DABCO催化的[4 + 2]与烯丙酸酯的β，γ-不饱和α-酮膦酸酯或β，γ-不饱和α-酮酸酯的环加成反应得到相应的高度官能化 四氢吡喃 和二氢吡喃衍生物，在温和条件下具有良好至优异的收率和中等至良好的区域选择性。
• 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.
• 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.
• Facile strategy for the preparation of pyrazoline derivatives through phosphine-promoted [2 + 3] cycloaddition of dialkyl azodicarboxylates with <font>β</font>,<font>γ</font>-unsaturated <font>α</font>-keto esters
  作者：Jin-Feng Zhang、Hong Pan、Tongfan Liu

  DOI：10.1080/00397911.2018.1435819

  日期：2018.5.3

  ABSTRACT A facile phosphine-promoted [2 + 3] cycloaddition of dialkyl azodicarboxylates with β,γ-unsaturated α-keto esters was developed, and a series of pyrazoline derivatives were obtained with good yields under mild conditions. Furthermore, the scope of the cyclizations was investigated. GRAPHICAL ABSTRACT

  摘要开发了一种简便的膦促进的偶氮二羧酸二烷基酯与β,γ-不饱和α-酮酯的[2+3]环加成反应，并在温和的条件下以良好的收率获得了一系列吡唑啉衍生物。此外，还研究了环化的范围。图形概要