methyl 4-oxo-4-phenyl-2-(1-thiophenyl)-butanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-oxo-4-phenyl-2-(1-thiophenyl)-butanoate
• 英文别名: Methyl 4-oxo-4-phenyl-2-thiophen-2-ylbutanoate
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: QJGAYGJPWAEUAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

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-(1-thiophenyl)-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。