2-(1-(4-methoxyphenyl)-2-nitroethyl)malononitrile | 1133396-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(1-(4-methoxyphenyl)-2-nitroethyl)malononitrile
• 英文别名: 2-[1-(4-Methoxyphenyl)-2-nitroethyl]propanedinitrile
• CAS: 1133396-07-2
• 化学式: C₁₂H₁₁N₃O₃
• 分子量: 245.238
• InChiKey: BNCIVJSURGJIJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-(4-methoxyphenyl)-2-nitroethyl)malononitrile 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 甲苯 为溶剂， 以90%的产率得到4-甲氧基-β-硝基苯乙烯
  参考文献：
  名称：

  金鸡纳生物碱和二碳酸二叔丁酯-DMAP促进（E）-硝基烯烃的高效合成

  摘要：

  由醛和烯烃合成硝基烯烃通常受到顺式和反式化合物混合物的形成的限制。在这里，我们报告了一种替代的，无金属的协议，适用于...

  DOI：

  10.1039/c6ra06644e
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 piperazine-grafted reduced graphene oxide (rGO-NH) 作用下， 以 乙醇 为溶剂， 反应 93.0h， 生成 2-(1-(4-methoxyphenyl)-2-nitroethyl)malononitrile
  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

• Efficient Method for the Synthesis of Michael Adducts Using Kaolin Preloaded with KOH
  作者：G. Srihari、M. Marthanda Murthy

  DOI：10.1080/00397910802439191

  日期：2009.2.9

  Abstract Michael addition of various active methylene compounds to β-nitrostyrenes is efficiently catalyzed by using Kaolin preloaded with KOH in acetonitrile at room temperature with moderate to good yields.

  摘要 在室温下，在乙腈中预载 KOH 的高岭土可以有效地催化各种活性亚甲基化合物与 β-硝基苯乙烯的迈克尔加成反应，收率适中。
• Reduced graphene oxide supported piperazine in aminocatalysis
  作者：Eduardo Rodrigo、Beatriz García Alcubilla、Raquel Sainz、J. L. García Fierro、Rafael Ferritto、M. Belén Cid

  DOI：10.1039/c4cc02701a

  日期：——

  Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions.

  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。
• Aqueous-mediated Michael Addition of Active Methylene Compounds with Nitroalkenes
  作者：Wenkai Dong、Dongcheng Xu、Jianwu Xie

  DOI：10.1002/cjoc.201200228

  日期：2012.8

  A simple, atom economical and highly efficient green protocol has been developed for the synthesis of Michael adducts of nitroalkenes and 2‐amino‐2‐chromene derivatives by Michael addition of active methylene compounds (such as malononitrile and ethyl cyanoacetate) to nitroalkenes under aqueous‐mediated conditions. This green approach provided the desired products in high yields and the reaction scope

  已开发出一种简单，原子经济且高效的绿色方案，用于在水溶液中，通过将活性亚甲基化合物（如丙二腈和氰基乙酸乙酯）迈克尔加成到硝基烯烃中，合成硝基烯烃和2-氨基-2-色烯衍生物的迈克尔加成产物。介导的条件。这种绿色方法以高收率提供了所需的产物，并且反应范围被证明是相当广泛的。
• Raghuvanshi, Raghvendra Singh; Singh, Manorama, Journal of the Indian Chemical Society, 2012, vol. 89, # 5, p. 679 - 682
  作者：Raghuvanshi, Raghvendra Singh、Singh, Manorama

  DOI：——

  日期：——
• 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.