(2R,3S)-2-ethyl-4-nitro-3-(2-nitrophenyl)butanal | 1192052-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-2-ethyl-4-nitro-3-(2-nitrophenyl)butanal
• CAS: 1192052-98-4
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: VBKISNZQIBEBPR-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-nitro-2-(2-nitrovinyl)benzene 、 正丁醛 在 C₁₅H₂₁N₃O₂ 、 S-1,1'-联-2-萘酚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到(2R,3S)-2-ethyl-4-nitro-3-(2-nitrophenyl)butanal
  参考文献：
  名称：

  Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by l-prolinamide derivatives using phenols as co-catalysts

  摘要：

  The asymmetric Michael addition of aldehydes to nitroolefins was investigated using L-prolinamide derivatives of 2-(2'-piperidinyl)pyridine as catalyst and a variety of phenols as co-catalyst. Extensive screening toward the effect of prolinamides, phenols, and solvents on this transformation revealed that a combination of (S)-2-(2'-piperidinyl)pyridine-derived trans-4-hydroxy-L-prolinamide 2c, (S)-1,1'-bi-2-naphthol, and dichloromethane was a promising system. This system was shown to be amenable to a rich variety of aldehydes and nitroolefins and afforded the nitroaldehyde products with excellent yield, enantiomeric excess (up to 99%) and diastereoselectivity ratio (up to 99/1), even in the case of 1 mol % catalyst loading and 1.5 equiv of aldehydes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.022

文献信息

• Synthesis of <i>N</i>-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments
  作者：José A. C. Delgado、Fidel E. M. Vicente、Alexander F. de la Torre、Vitor A. Fernandes、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1039/d1nj01112j

  日期：——

  through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Consequently, they have further been evaluated in the 1,4-addition of aldehydes to trans-β-nitrostyrene having water as the sole solvent. Under sustainable reaction conditions, Michael adducts were obtained in excellent yields

  通过基于异氰化物的多组分反应合成了N-烷基化脂肽有机催化剂库。各种结构基序被可调地引入到催化剂骨架上，目的是结合两亲性特征。因此，它们已在醛与反式-β-硝基苯乙烯的 1,4-加成反应中得到进一步评估，其中水作为唯一溶剂。在可持续的反应条件下，迈克尔加合物以优异的产率、非对映选择性和对映选择性获得，使用低催化剂负载量且无添加剂。