ethyl 2-(4-nitrobenzoyl)-4-oxo-4-phenylbut-2-enoate | 1446352-55-1

• 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: ethyl 2-(4-nitrobenzoyl)-4-oxo-4-phenylbut-2-enoate
• 英文别名: ethyl (Z)-2-(4-nitrobenzoyl)-4-oxo-4-phenylbut-2-enoate
• CAS: 1446352-55-1
• 化学式: C₁₉H₁₅NO₆
• 分子量: 353.331
• InChiKey: VKXBVXGVYKRKTL-VBKFSLOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 生成 ethyl 2-(4-nitrobenzoyl)-4-oxo-4-phenylbut-2-enoate 、 ethyl 2-(4-nitrobenzoyl)-4-oxo-4-phenylbut-2-enoate
  参考文献：
  名称：

  Target-oriented synthesis: miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.05.106

文献信息

• 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.