(2R,3S)-2-ethyl-4-nitro-3-(3-nitrophenyl)butanal | 1192052-95-1

• 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-(3-nitrophenyl)butanal
• CAS: 1192052-95-1
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: BKARMZSEDBUKIV-CABZTGNLSA-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：

  3-nitro-β-nitrostyrene 、 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93%的产率得到(2R,3S)-2-ethyl-4-nitro-3-(3-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

• Multicomponent Approach to Silica-Grafted Peptide Catalysts: A 3 D Continuous-Flow Organocatalytic System with On-line Monitoring of Conversion and Stereoselectivity
  作者：Gabriel S. Scatena、Alexander F. de la Torre、Quezia B. Cass、Daniel G. Rivera、Márcio W. Paixão

  DOI：10.1002/cctc.201402501

  日期：2014.11

  prolyl‐peptide catalysts by a multicomponent reaction that enables the simultaneous incorporation of the catalytic and the heterogenizable (triethoxysilane) moieties. A microreactor with high catalytic efficacy and reproducibly in the conjugate addition of aldehydes to nitroolefins was obtained by grafting onto HPLC‐grade silica (10 μm) and packing into a column with a selected catalyst. A 3 D continuous‐flow

  通常通过逐步合成来实现具有适合于锚固在固体载体上的功能性附件的有机催化剂的衍生化。作为这种策略的替代方法，这项工作描述了通过多组分反应对硅烷化的脯氨酰肽催化剂进行单罐方法，该方法能够同时引入催化部分和可杂化的（三乙氧基硅烷）部分。通过将接枝到HPLC级二氧化硅（10μm）上并用选定的催化剂填充到色谱柱中，可以获得具有高催化效率且可重复地将醛共轭添加到硝基烯烃中的微反应器。建立了一个3D连续流系统，该系统包括对反应结果的在线监控。为了那个原因，将微反应器连接到色谱柱上，以从第二维中的迈克尔加合物中分离出剩余的底物，然后是手性多糖柱，用于分析转化率和立体选择性。这种方法代表了一种新的仪器设置，结合了多维色谱和流催化的优点。
• Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds
  作者：Karla S. Feu、Alexander F. de la Torre、Sandrina Silva、Marco A. F. de Moraes Junior、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1039/c4gc00098f

  日期：——

  A highly stereoselective organocatalytic Michael addition of aldehydes to trans-β-nitrostyrenes using PEG as a recyclable solvent medium is presented.

  通过使用PEG作为可回收溶剂介质，展示了对醛高度立体选择性的有机催化Michael加成反应，该反应将醛加到trans-β-硝基苯乙烯上。
• Multicomponent Combinatorial Development and Conformational Analysis of Prolyl Peptide–Peptoid Hybrid Catalysts: Application in the Direct Asymmetric Michael Addition
  作者：Alexander F. de la Torre、Daniel G. Rivera、Marco A. B. Ferreira、Arlene G. Corrêa、Márcio W. Paixão

  DOI：10.1021/jo401609z

  日期：2013.10.18

  amino acid substituents. The catalytic behavior of the peptide–peptoid hybrids was assessed in the asymmetric conjugate addition of aldehydes to nitroolefins, where most of the catalysts showed great efficacy and rendered the Michael adducts with good to excellent enantio- and diastereoselectivity. A molecular modeling study was performed for two distinct catalysts aiming to understand their conformational

  在新的脯氨酰肽-类肽杂化催化剂的开发中，采用了基于Ugi四组分反应的溶液相组合方法。在创建催化剂组期间，多样性的三个不同元素发生了变化：胺，氧代和异氰基组分。此过程的多组分性质使得能够直接生成具有通用序列Pro- N -R 1 -Xaa-NHR 3的一系列肽-类肽杂化物，其中Xaa为Gly（R 2 = H）或Aib（R 2 = gem -Me）以及R 1和R 3烷基或氨基酸取代基。通过将醛不对称共轭加成到硝基烯烃中来评估肽-类肽杂化物的催化行为，其中大多数催化剂显示出很高的功效，并使迈克尔加成物具有良好的对映体和非对映体选择性。为了了解其构象特征，对两种不同的催化剂进行了分子建模研究。构象分析为理解有机催化转化过程中实现的显着立体控制提供了重要信息。
• Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by l-prolinamide derivatives using phenols as co-catalysts
  作者：Yan-Qin Cheng、Zheng Bian、Ya-Bing He、Fu-She Han、Chuan-Qing Kang、Zhao-Lun Ning、Lian-Xun Gao

  DOI：10.1016/j.tetasy.2009.07.022

  日期：2009.8

  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.