diethyl 2-(1-amino-3-phenylpropylidene)malonate | 1353674-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-(1-amino-3-phenylpropylidene)malonate
• 英文别名: Diethyl 2-(1-amino-3-phenylpropylidene)propanedioate；diethyl 2-(1-amino-3-phenylpropylidene)propanedioate
• CAS: 1353674-40-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: RAKHMSCRXMQYBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-苯基丙酰胺 在 劳森试剂 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 28.0h， 生成 diethyl 2-(1-amino-3-phenylpropylidene)malonate
  参考文献：
  名称：

  钌催化合成烯胺酮

  摘要：

  已经发现，Grubbs第一代催化剂是通过将硫酰胺与α-重氮二羰基化合物偶合来合成烯胺酮的有效催化剂。该反应成功地将伯，仲和叔硫酰胺转化为其相应的烯胺酮。该反应也适用于手性烯胺酮的合成。

  DOI：

  10.1021/ol202812d

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 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。
• 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。
• 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.
• Ruthenium Catalyzed Synthesis of Enaminones
  作者：Naga Durgarao Koduri、Halee Scott、Bethany Hileman、Justin D. Cox、Michael Coffin、Lindsay Glicksberg、Syed R. Hussaini

  DOI：10.1021/ol202812d

  日期：2012.1.20

  catalyst has been found to be an effective catalyst for the synthesis of enaminones by coupling thioamides with α-diazodicarbonyl compounds. The reaction is successful in converting primary, secondary, and tertiary thioamides into their corresponding enaminones. The reaction is also suitable for the synthesis of chiral enaminones.

  已经发现，Grubbs第一代催化剂是通过将硫酰胺与α-重氮二羰基化合物偶合来合成烯胺酮的有效催化剂。该反应成功地将伯，仲和叔硫酰胺转化为其相应的烯胺酮。该反应也适用于手性烯胺酮的合成。