2-(1-(4-methylphenyl)-2-nitroethyl)malononitrile | 1133396-08-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(1-(4-methylphenyl)-2-nitroethyl)malononitrile
• 英文别名: 2-[1-(4-Methylphenyl)-2-nitroethyl]propanedinitrile
• CAS: 1133396-08-3
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: YHBYEBHUDUWDAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-(4-methylphenyl)-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86%的产率得到(E)-2-(4-methylphenyl)-1-nitroethene
  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：

  对甲基苯甲醛 在 奎尼丁 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2-(1-(4-methylphenyl)-2-nitroethyl)malononitrile
  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

文献信息

• 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。
• 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.
• Cinchona alkaloid and di-tert-butyldicarbonate–DMAP promoted efficient synthesis of (E)-nitroolefins
  作者：Nataraj Poomathi、Paramasivan T. Perumal

  DOI：10.1039/c6ra06644e

  日期：——

  Synthesis of nitroolefins from aldehyde and olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report an alternative, metal- free protocol for the...

  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...