Ethyl 3-(4-methylphenyl)-2,4-dinitrobutanoate | 1071166-75-0

• 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: Ethyl 3-(4-methylphenyl)-2,4-dinitrobutanoate
• CAS: 1071166-75-0
• 化学式: C₁₃H₁₆N₂O₆
• 分子量: 296.28
• InChiKey: STICQURFOAULJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  硝基乙酸乙酯 、 (E)-2-(4-methylphenyl)-1-nitroethene 在 Amberlite IRA₉₀₀F 作用下， 反应 4.0h， 以96%的产率得到Ethyl 3-(4-methylphenyl)-2,4-dinitrobutanoate
  参考文献：
  名称：

  Amberlite IRA900F 作为固体氟化物源，用于在无溶剂条件下进行各种有机转化

  摘要：

  我们已经报道，Amberlite IRA900F (Amb-F) 是一种有效的无金属催化剂，用于在无溶剂条件下激活 Si-N 和 Si-O 键和各种有机转化中的温和碱，例如添加将 TMSN3 转化为 (E)-2-芳基-1-氰基-1-硝基乙烯、腈、α,β-不饱和酸及其酯，以及将二甲基甲硅烷基乙烯酮缩醛和硝基乙酸乙酯加成到 β-硝基苯乙烯。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800142

文献信息

• 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.