(S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate | 1421277-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS: 1421277-03-3
• 化学式: C₁₅H₁₇NO₃S
• 分子量: 291.371
• InChiKey: FJWBJOSKGSRNCM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-2-carboxylate 在 (CuOTf)₂*Tol 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以95%的产率得到
  参考文献：
  名称：

  铜催化的硫代酰胺与α-重氮羰基化合物的化学选择性交叉偶联反应：烯胺酮的合成

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2017.01.004
• 作为产物：
  描述：

  2-溴苯乙酮 在 Grubbs catalyst first generation 、 N,N′-双(对甲苯磺酰)肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.08h， 生成 (S)-ethyl 5-((2-oxo-2-phenylethyl)thio)-3,4-dihydro-2H-pyrrole-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

• Acceleration of the Eschenmoser coupling reaction by sonication: efficient synthesis of enaminones
  作者：Naga Durgarao Koduri、Bethany Hileman、Justin D. Cox、Halee Scott、Phuong Hoang、Alexa Robbins、Kyle Bowers、Lemma Tsebaot、Kun Miao、Maria Castaneda、Michael Coffin、Guan Wei、Tim D. W. Claridge、Kenneth P. Roberts、Syed Raziullah Hussaini

  DOI：10.1039/c2ra22033d

  日期：——

  Enaminones are commonly prepared by the Eschenmoser coupling reaction. The duration of the reaction is often long. Here, we describe how sonication can accelerate this reaction. The reaction conditions provide an efficient method for the coupling of primary, secondary and tertiary thioamides with α-bromocarbonyl compounds.

  烯胺酮通常通过Eschenmoser偶联反应制备。反应的持续时间通常很长。在这里，我们描述了超声处理如何加速该反应。反应条件为伯，仲和叔硫酰胺与α-溴羰基化合物的偶联提供了一种有效的方法。