methyl 4-oxo-4-phenyl-2-(4-bromophenyl)-butanoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: methyl 4-oxo-4-phenyl-2-(4-bromophenyl)-butanoate
• 英文别名: Methyl 2-(4-bromophenyl)-4-oxo-4-phenylbutanoate
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: HJKWADJTZUJZQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(1-苯基乙烯基)吗啉 在 bis(1,1,1-trifluoroacetylacetonato)copper(II) 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4-oxo-4-phenyl-2-(4-bromophenyl)-butanoate
  参考文献：
  名称：

  Unusual reaction of aryldiazoacetates with enamines: highly effective synthesis of γ-ketoesters

  摘要：

  The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided gamma-ketoesters in good yields. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a gamma-ketoester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.086

文献信息

• New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes
  作者：Wei-Jie Zhao、Ming Yan、Dan Huang、Shun-Jun Ji

  DOI：10.1016/j.tet.2005.03.093

  日期：2005.6

  The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided γ-keto esters in good yields. A full investigation of the effects of solvents, catalysts, enamines and aryldiazoacetates on the reaction was carried out. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a

  铜和铑配合物催化的芳基重氮乙酸酯与烯胺的反应以高收率提供了γ-酮酯。全面研究了溶剂，催化剂，烯胺和芳基重氮乙酸酯对反应的影响。粗反应混合物的仔细分析表明，取代的烯胺为主要产物，其在硅胶上水解，得到γ-酮酯为最终产物。提出了一种将烯胺亲核加成至金属卡宾并随后进行氢转移的反应机理。检查了手性二铑和铜催化剂，发现它们提供了没有对映选择性的γ-酮酯。该结果可以根据提出的反应机理进行合理化。用几种亲电试剂捕获烯胺中间体的尝试未成功。
• One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of <i>cis</i> -α,γ-Substituted-γ-Butyrolactones
  作者：Sara Meninno、Chiara Volpe、Alessandra Lattanzi

  DOI：10.1002/adsc.201600427

  日期：2016.9.1

  enantioselective one‐pot synthesis of important building blocks, α‐chiral γ‐keto esters, has been developed by combining a quinine‐catalyzed Michael addition of malononitrile to trans‐enones followed by magnesium monoperoxyphthalate (MMPP) oxidation. These synthons proved to be useful reagents for a simple access to challenging cis‐α,γ‐disubstituted γ‐butyrolactones in good diastereoselectivity and

  通过结合奎宁催化的丙二醛向反式烯酮的迈克尔加成反应以及随后的单过氧邻苯二甲酸镁（MMPP）氧化反应，已经开发出了对映体选择性很强的重要组成部分，α-手性γ-酮酯。这些合成子被证明是有用的试剂，用于以良好的非对映选择性和高对映体控制容易地获得具有挑战性的顺式， α，γ-二取代的γ-丁内酯。
• Visible-Light-Promoted Carbene Insertion and Decarbonylation for the Synthesis of α-Substituted γ-Ketoesters
  作者：Weina Li、Yingying Yang、Zhiliang Tang、Xianglin Yu、Jun Lin、Yi Jin

  DOI：10.1021/acs.joc.2c01552

  日期：2022.10.7

  a blue visible-light-promoted approach for preparing a variety of α-substituted γ-ketoester derivatives through carbene insertion and the decarbonylation of enaminones and diazoesters. These reactions use readily available starting materials and transition-metal-free, eco-friendly procedures that are amenable to gram-scale synthesis and wide functional group tolerance. This methodology may be useful

  在此，我们报告了一种蓝色可见光促进的方法，用于通过卡宾插入和烯胺酮和重氮酯的脱羰制备各种 α-取代的 γ-酮酯衍生物。这些反应使用容易获得的起始材料和不含过渡金属的环保程序，这些程序适合克级合成和广泛的官能团耐受性。该方法可用于构建具有潜在生物活性的多取代杂环。
• Unusual reaction of aryldiazoacetates with enamines: highly effective synthesis of γ-ketoesters
  作者：Ming Yan、Wei-Jie Zhao、Dan Huang、Shun-Jun Ji

  DOI：10.1016/j.tetlet.2004.06.086

  日期：2004.8

  The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided gamma-ketoesters in good yields. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a gamma-ketoester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed. (C) 2004 Elsevier Ltd. All rights reserved.