diethyl 2-[4-nitrophenyl(piperidin-1-yl)methylene]malonate | 38238-96-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl 2-[4-nitrophenyl(piperidin-1-yl)methylene]malonate
• CAS: 38238-96-9
• 化学式: C₁₉H₂₄N₂O₆
• 分子量: 376.409
• InChiKey: MCGFVKAGUICKRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.98
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  哌啶 、 diethyl 2-<(methylsulfonyl)oxy>-2-(p-nitrophenyl)ethylene-1,1-dicarboxylate 以 乙腈 为溶剂， 生成 diethyl 2-[4-nitrophenyl(piperidin-1-yl)methylene]malonate
  参考文献：
  名称：

  Triflate/Mesylate Ratios and Competing C−O and S−O Bond Cleavages in Nucleophilic Vinylic Substitution

  摘要：

  In an attempt to develop the k(OTf)/K-OMs ratio as a mechanistic tool for the ''addition-elimination'' route in nucleophilic vinylic substitution, several pairs of vinyl mesylates and triflates were prepared. Whereas reactions of ArC(LG)=C(CO(2)Et)(2) (LG = OTf, OMs) with piperidine and morpholine in MeCN or THF gave the normal substitution product with k(OTf)/k(OMs) ratios of 4.3-10.6, the reaction of the mesylates, Ar = p-O2NC6H4, and of PhC(OMs)=C(Me)CN with MeS(-) gave a ketone via an S-O bond cleavage. A related mesityl-substituted tosylate also reacted with p-MeC(6)H(4)X(-) (X = O, S) via an S-O bond cleavage. Hence, k(OTf)/k(OMs) ratios cannot be used as a general mechanistic tool. Several reactivity ratios in vinylic substitution are briefly discussed.

  DOI：

  10.1021/jo961108t

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。