(S,Z)-ethyl 5-(2-oxo-2-phenylethylidene)pyrrolidine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,Z)-ethyl 5-(2-oxo-2-phenylethylidene)pyrrolidine-2-carboxylate
• 英文别名: ethyl (2S,5Z)-5-phenacylidenepyrrolidine-2-carboxylate
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: ROACPGFNVLASRG-UKVQZPPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 20.0h， 以83%的产率得到(S,Z)-ethyl 5-(2-oxo-2-phenylethylidene)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Enaminones via Ruthenium-Catalyzed Coupling of Thioamides and α-Diazocarbonyl Compounds

  摘要：

  Enaminones can be prepared via the Rh2(OAc)4-catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.

  DOI：

  10.1021/jo5011312

文献信息

• Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones
  作者：Arpal Pal、Naga D. Koduri、Zhiguo Wang、Erika Lopez Quiroz、Alexandra Chong、Matthew Vuong、Nisha Rajagopal、Michael Nguyen、Kenneth P. Roberts、Syed R. Hussaini

  DOI：10.1016/j.tetlet.2017.01.004

  日期：2017.2

  formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary

  在药物，农业化学和材料研究中，开发用于C C键形成反应的操作简单且经济高效的方法非常重要。在本文中，我们描述了硫酰胺与受主/受主取代的和仅受主取代的α-重氮羰基化合物在铜催化下的交叉偶联反应，从而生成烯胺酮。该反应在硫酰胺和重氮羰基化合物方面显示出广泛的底物范围。伯，仲和叔硫酰胺与α-重氮二酯，α-重氮酮酸酯，α-二重氮酮，α-二重氮酮酰胺，α-二重氮酰胺，α-二重氮酮砜和α-二重氮酮反应时均会产生烯胺酮。
• A Convenient Protocol for the Alkylidenation of Lactams
  作者：Mark C. Elliott、Stuart V. Wordingham

  DOI：10.1055/s-2006-926390

  日期：——

  A convenient two-step preparation of alkylidenepyrrolidines is reported.

  报告了一种便捷的两步法制备亚烷基吡咯烷类化合物的方法。