(Z)-2-benzoyl-4-oxo-4-phenylbut-2-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (Z)-2-benzoyl-4-oxo-4-phenylbut-2-enoic acid ethyl ester
• 英文别名: ethyl 2-benzoyl-4-oxo-4-phenylbut-2-enoate；ethyl (Z)-2-benzoyl-4-oxo-4-phenylbut-2-enoate
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: OULHFHMBHNYMQN-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-benzoyl-4-oxo-4-phenylbut-2-enoic acid ethyl ester 、 二叔丁基过氧化物 、 三乙胺 、 氯仿 以30%的产率得到
  参考文献：
  名称：

  GRAZIANO, M. L.;IESCE, M. R.;SCARPATI, R., SYNTHESIS, BRD, 1984, N 1, 66-68

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-Diphenyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid ethyl ester 以3%的产率得到
  参考文献：
  名称：

  GRAZIANO, M. L.;IESCE, M. R.;SCARPATI, R., J. CHEM. SOC. PERKIN TRANS. PART 1, 1982, N 9, 2007-2012

  摘要：

  DOI：

文献信息

• Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes
  作者：Meng Gao、Yan Yang、Yan-Dong Wu、Cong Deng、Li-Ping Cao、Xiang-Gao Meng、An-Xin Wu

  DOI：10.1021/ol100473f

  日期：2010.4.16

  A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones

  通过聚焦多米诺骨牌战略已开发出一种由1,3-二羰基化合物和甲基酮或末端芳基烯烃高效合成不对称1,4-二烯键的方法。简单且容易获得的起始原料，温和的反应条件和非常简单的操作是反应的优势，可以直接合成各种不对称的1,4-二烯酮。
• I₂/Cu-mediated self-sorting domino reaction of aryl β-ketoesters into symmetrical 2-carboalkoxy-1,4-enediones: application to synthesis of pyrazine, β-carboline and quinoxalines
  作者：Gandhesiri Satish、Andivelu Ilangovan

  DOI：10.1039/c5ra08030d

  日期：——

  A self-sorting domino reaction of aryl β-ketoesters into symmetrical 1,4-enediones is reported by an I₂/Cu system.

  一种I₂/Cu体系报告的芳基β-酮酯的自排序多米诺反应可将其转化为对称的1,4-烯二酮。
• Ceric Ammonium Nitrate Promoted Oxidative Coupling of Terminal Alkynes and 1,3-Keto Esters: A Synthesis of Unsymmetrical 1,1,2-Triacylalkenes
  作者：Charnsak Thongsornkleeb、Sureeporn Ruengsangtongkul、Takahito Kuribara、Nattawadee Chaisan、Jumreang Tummatorn、Somsak Ruchirawat

  DOI：10.1055/a-1774-6966

  日期：2022.9

  Unsymmetrical 1,1,2-triacylalkenes were conveniently prepared by the oxidative coupling of 1,3-keto esters with terminal alkynes by employing 4.0 equivalents of inexpensive ceric ammonium nitrate (CAN) as the oxidant in acetonitrile as the solvent at 0 °C. The method is milder than previously reported methods and can be conducted under air, thereby demonstrating its practicality and versatility for

  不对称的 1,1,2-三酰基烯烃是通过 1,3-酮酯与末端炔烃的氧化偶联，在 0 °C 下使用 4.0 当量廉价的硝酸铈铵 (CAN) 作为氧化剂，以乙腈为溶剂，方便地制备的。该方法比以前报道的方法更温和，并且可以在空气中进行，从而证明了它在制备这些有用的构件方面的实用性和多功能性。该反应被认为是通过由 CAN 引发的 1,3-酮酯底物的单电子转移过程发生的，以产生 α-自由基物质，该物质迅速添加到反应中的末端炔烃伴侣。随后通过空气和 CAN 对所得乙烯基自由基进行氧化，然后导致形成作为 E 和 Z 异构体混合物的三酰基烯烃产物。反应被证明是一般的，
• Target-oriented synthesis: miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates
  作者：Yan-ping Zhu、Qun Cai、Qing-he Gao、Feng-cheng Jia、Mei-cai Liu、Meng Gao、An-xin Wu

  DOI：10.1016/j.tet.2013.05.106

  日期：2013.8

  Target-oriented synthetic protocol was presented for the synthesis of 1,4-enediones. The approach can efficiently construct 1,4-enediones through different reaction pathways from multiform substrates alpha-halo aromatic ketones, 2-hydroxy-aromatic ketones and methyl carbinols. In this reaction, CuI was found to be the most efficient catalyst. Multiform substrates were also found to perform well to afford the products in a one-pot fashion. (C) 2013 Elsevier Ltd. All rights reserved.
• Heterogeneous synthesis of 1,4-enediones and 1,4-diketones with manganese oxide molecular sieves OMS-2 as a recyclable catalyst
  作者：Xu Meng、Jinqi Zhang、Gexin Chen、Baohua Chen、Peiqing Zhao

  DOI：10.1016/j.catcom.2015.07.003

  日期：2015.9

  An efficient manganese oxide octahedral molecular sieves OMS-2-catalyzed chemoselective synthesis of 1,4-enediones and 1,4-diketones from 1,3-dicarbonyls and alpha-iodoacetophenones is described. The present catalytic system can be applied in one-pot, three-component reactions of methyl ketones, 1,3-dicarbonyls and iodine. Moreover, OMS-2 can be reused at least 5 times without loss of activity. (C) 2015 Elsevier B.V. All rights reserved.