ethyl 2-cyano-3-(4-methoxyphenyl)-4-nitrobutanoate | 1415728-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-cyano-3-(4-methoxyphenyl)-4-nitrobutanoate
• CAS: 1415728-78-7
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: QETQSRNDZVSESF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 氰乙酸乙酯 在 piperazine-grafted reduced graphene oxide (rGO-NH) 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 ethyl 2-cyano-3-(4-methoxyphenyl)-4-nitrobutanoate
  参考文献：
  名称：

  Reduced graphene oxide supported piperazine in aminocatalysis

  摘要：

  还原氧化石墨烯（rGO）被用作哌嗪的载体，以提供一种能够高效促进老式有机转化反应的异相双功能有机催化剂（rGO-NH），例如Knoevenagel反应、迈克尔反应和醛醇反应。获得的结果表明，载体在这些反应过程中发挥了重要作用。

  DOI：

  10.1039/c4cc02701a

文献信息

• Organic amine grafting on mesoporous silica as a hybrid catalyst for heterogeneous three-component one-pot reaction
  作者：Kenichi Komura、Yuta Mishima、Mamoru Koketsu

  DOI：10.1016/j.apcata.2012.08.009

  日期：2012.11

  organic–inorganic hybrid catalyst was prepared by immobilizing 3-methylaminopropyl moiety onto mesoporous silica, MCM-41, and applied for solid base catalyst of three-component one-pot reaction, i.e. Knoevenagel condensation of aldehyde with the active methylene compound to yield an electron deficient alkene which is subjective to be reacted with nitromethane by Michael addition to form tri-substituted

  有机-无机杂化催化剂是通过将3-甲基氨基丙基部分固定在介孔二氧化硅MCM-41上制备的，并用于三组分一锅法反应的固体基础催化剂，即醛与活性亚甲基化合物的Knoevenagel缩合反应得到电子不足的烯烃，其易于通过迈克尔加成与硝基甲烷反应形成三取代的伯硝基化合物。通过粉末XRD，TG-DTA，FT-IR，氮吸附-脱附测量和固态交叉极化幻角旋转（CP / MAS）NMR表征该催化剂，并在三组分一锅法中表现出高催化活性。反应; 但是，可重用性较差。
• Fe3O4@L-arginine and Fe3O4@L-histidine nanoparticles for one-pot solvent-free sequential Knoevenagel–Michael addition reactions
  作者：Bindi Sanghavi、Hemant P. Soni

  DOI：10.1007/s11164-023-05017-3

  日期：2023.9

  Fe3O4@L-Histidine nanoparticles (NPs) are synthesized and explored as catalysts for the sequential Knoevenagel condensation and Michael addition reactions (KMS). The reaction parameters like the amount of catalyst, temperature, and solvent systems are optimized for both of the catalysts for the Knoevenagel condensation reaction. It was observed that the developed catalyst systems work well under solvent-free conditions

  合成了Fe 3 O 4 @L-精氨酸和 Fe 3 O 4 @L-组氨酸纳米颗粒 (NP)，并将其作为连续 Knoevenagel 缩合和迈克尔加成反应 (KMS) 的催化剂进行了探索。催化剂用量、温度和溶剂系统等反应参数针对 Knoevenagel 缩合反应的两种催化剂进行了优化。据观察，所开发的催化剂体系在 80 °C 的无溶剂条件下运行良好。相应的 Knoevenagel 加合物（高达 97%）实现了优异到高产率，反过来，Michael 产品实现了良好的产率（高达 70%）。令人惊讶的是，Fe 3 O 4@L-Hist NPs 没有显示出任何连续迈克尔添加的催化活性。已经讨论了用于 KMS 的Fe 3 O 4 @L-Arg NPs高活性的可能原因。催化剂也被回收并重复使用 5 个循环，在活性和选择性方面具有相同的性能。连续 Knoevenagel 缩合和迈克尔加成反应的优化方案可以在节
• Tris-ureas as versatile and highly efficient organocatalysts for Michael addition reactions of nitro-olefins: Mechanistic insight from in-situ diagnostics
  作者：Milan Bera、Tamal Kanti Ghosh、Bidyut Akhuli、Pradyut Ghosh

  DOI：10.1016/j.molcata.2015.01.004

  日期：2015.11

  Tris(2-aminoethyl)-amine, TREN based tris-ureas (1a-1d) and tris-thiourea (1e) have been explored towards a wide range of catalytic Michael addition reactions. These tris-ureas, 1a-1d efficiently catalyze the addition reaction of beta-nitro styrenes (2a-2d) with various nucleophiles such as beta-ketoesters (3a-3c), 1,3-dicarbonyl compound (3d), a cyanoester (3e) and a nitroester (3f) under ambient conditions to produce corresponding nitro alkanes in high yields. Pentafluorophenyl attached tris-urea, 1d is found to be the most effective catalyst in the series that yields 78-98% products conversion. In case of the reaction between beta-nitro styrenes and malononitrile (3g) in presence of 1d, 2-amino-5-nitro-4,6-diphenylcyclohex-1-ene-1,3,3-tricarbonitriles are also isolated as a minor product along with the corresponding Michael adduct. The added advantage of bridge-head nitrogen center in tris-urea organocatalysts, 1a-1d has been established by studying analogous benzene platform based tris-ureas (1f, 1g, 1h) in similar experimental conditions. Furthermore, a plausible reaction mechanism has also been established based on in-situ H-1 NMR kinetic studies. (C) 2015 Elsevier B.V. All rights reserved.