diethyl 2-(1-((4-methoxyphenyl)amino)ethylidene)malonate | 1621003-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-(1-((4-methoxyphenyl)amino)ethylidene)malonate
• 英文别名: Diethyl 2-[1-(4-methoxyanilino)ethylidene]propanedioate；diethyl 2-[1-(4-methoxyanilino)ethylidene]propanedioate
• CAS: 1621003-92-6
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: AWLZJHHNLYYVJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 劳森试剂 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 diethyl 2-(1-((4-methoxyphenyl)amino)ethylidene)malonate
  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

• A copper(I)-complexed magnetic nanoparticle catalyst for enaminone synthesis
  作者：Leila Mohammadi、Mohammad Ali Zolfigol、Mahsa Ebrahiminia、Kenneth P. Roberts、Samira Ansari、Tahereh Azadbakht、Syed R. Hussaini

  DOI：10.1016/j.catcom.2017.08.022

  日期：2017.12

  The synthesis of a copper(I)-complexed magnetic nanoparticle catalyst is described. The catalyst was characterized using Fourier transform infrared spectroscopy (FT–IR), energy-dispersive X-ray spectroscopy (XPS), atomic absrobtion spectroscopy (AA), thermogravimetric analysis (TGA), vibrating sample magnetometery (VSM), X-ray photoelectron spectroscopy (XPS), scanning electron miscroscopy (SEM) and

  描述了铜（I）-络合的磁性纳米颗粒催化剂的合成。使用傅里叶变换红外光谱（FT-IR），能量色散X射线光谱（XPS），原子吸收光谱（AA），热重分析（TGA），振动样品磁强（VSM），X射线光电子来表征催化剂光谱（XPS），扫描电子显微镜（SEM）和透射电子显微镜（TEM）。该催化剂偶联硫代酰胺和重氮羰基化合物以产生各种烯胺酮。该催化剂减少了反应时间和温度，并以高收率和选择性提供了烯胺酮。此外，催化剂可以通过磁体分离并再循环。
• Enaminones via Ruthenium-Catalyzed Coupling of Thioamides and α-Diazocarbonyl Compounds
  作者：Naga D. Koduri、Zhiguo Wang、Garrett Cannell、Kate Cooley、Tsebaot Mesfin Lemma、Kun Miao、Michael Nguyen、Bram Frohock、Maria Castaneda、Halee Scott、Dragos Albinescu、Syed R. Hussaini

  DOI：10.1021/jo5011312

  日期：2014.8.15

  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.