(2S,3R)-2-methyl-4-nitro-3-(p-tolyl)butanal

• 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: (2S,3R)-2-methyl-4-nitro-3-(p-tolyl)butanal
• 英文别名: (2S,3R)-2-methyl-3-(4-methylphenyl)-4-nitrobutanal
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: PCLKSIWENRGUGK-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-methyl-β-nitrostyrene 、 丙醛 在 Fe3O4 nanoparticles hybridized with diphenylprolinol silylether moiety decorated κ-carrageenan 作用下， 以 neat (no solvent) 为溶剂， 以58%的产率得到(2S,3R)-2-methyl-4-nitro-3-(p-tolyl)butanal
  参考文献：
  名称：

  杂化磁性材料（Fe 3 O 4 –κ-角叉菜胶）作为醛向硝基烯烃的迈克尔加成反应的催化剂

  摘要：

  已经从κ-角叉菜胶和Fe 3 O 4纳米颗粒制备了两种杂化磁性材料，并测试了将醛迈克尔加成到硝基烯烃中的催化剂。值得注意的是，由未修饰的κ-角叉菜胶制备的材料在选择的反应中表现出催化活性，而各个组分没有活性。这指出了MNP与κ-角叉菜胶之间的协同作用。还显示了带有二苯基脯氨醇甲硅烷基醚部分的第二种催化剂促进了反应，从而在优异的ee中产生了相应的加合物。反应完成后，可通过简单的磁倾析法方便地回收催化剂。

  DOI：

  10.1016/j.tet.2014.06.063

文献信息

• Novel Easily Recyclable Bifunctional Phosphonic Acid Carrying Tripeptides for the Stereoselective Michael Addition of Aldehydes with Nitroalkenes
  作者：Margery Cortes-Clerget、Olivier Gager、Maelle Monteil、Jean-Luc Pirat、Evelyne Migianu-Griffoni、Julia Deschamp、Marc Lecouvey

  DOI：10.1002/adsc.201500794

  日期：2016.1.7

  A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation was used for the first time as an efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes with good selectivities up to 95:5 dr and 93:7 er. Due to their high water solubility, the catalysts were easily recyclable and could be reused over several cycles

  首次将结合了氨基催化和膦酸活化的新型双功能有机催化剂库作为有效的工具，用于醛与几种芳香族硝基烯烃的立体选择性迈克尔加成反应，选择性高达95：5 dr和93：7 er。由于它们的高水溶性，这些催化剂易于回收利用，并且可以在多个循环中重复使用，而没有任何明显的选择性损失。
• Functionalization of Fe3O4 magnetic nanoparticles for organocatalytic Michael reactions
  作者：Paola Riente、Carolina Mendoza、Miquel A. Pericás

  DOI：10.1039/c1jm10535c

  日期：——

  (S)-α,α-Diphenylprolinol trimethylsilyl ether supported onto well-defined (5.7 ± 1.1 nm) superparamagnetic Fe3O4 nanoparticles was used as a highly active, magnetically recoverable and reusable catalyst for the asymmetric, organocatalytic Michael addition of propanal to nitroolefins leading to high enantioselectivities. The assembly of the catalytic functional nanoparticles involves two successive steps: (i) introduction of a 3-azidopropyl unit through the formation of Si–O bonds, and (ii) integration of the organocatalytic unit by means of a copper-catalysed alkyne–azide cycloaddition reaction leading to a 1,2,3-triazole linker. Neither the process of nanoparticle assembly nor its catalytic use in dichloromethane solution provokes particle growth or agglomeration, this behaviour being key for the observation of high catalytic activity and for recyclability.

  (S)-α,α-二苯基丙醇内酰胺三甲基硅醚负载于定义良好的（5.7 ± 1.1 纳米）超顺磁性Fe3O4纳米粒子上，被用作一种高活性、磁性可回收和可重复使用的催化剂，用于不对称有机催化米克尔加成反应，其中丙醛与硝基烯烃加成，得到高对映选择性产物。催化功能纳米粒子的组装涉及两个连续步骤：（i）通过形成Si–O键引入3-叠氮丙基单元，以及（ii）通过铜催化的炔烃-叠氮环加成反应将有机催化单元整合到1,2,3-三唑连接子上。无论是在纳米粒子组装过程中还是在二氯甲烷溶液中的催化使用过程中，都不会引发粒子生长或聚集，这种行为对于观察到高催化活性和可回收性至关重要。
• The Use ofN-Alkyl-2,2′-bipyrrolidine Derivatives as Organocatalysts for the Asymmetric Michael Addition of Ketones and Aldehydes to Nitroolefins
  作者：Olivier Andrey、Alexandre Alexakis、Axel Tomassini、Gerald Bernardinelli

  DOI：10.1002/adsc.200404037

  日期：2004.8

  The direct Michael addition of aldehydes and ketones to nitroolefins, catalyzed by N-i-Pr-2,2′-bipyrrolidine, is described. The desired 1,4-adducts are obtained in excellent yields with enantioselectivities up to 95% ee and dr up to 95 : 5 of the syn aldehyde addition product. An unexpected inversion of diastereoselectivity was observed for the addition of α-hydroxy ketones to β-arylnitroolefins with

  描述了由Ni -Pr-2，2'-联吡咯烷催化的醛和酮直接迈克尔加成到硝基烯烃上。以优异的产率获得所需的1,4-加合物，其对映体选择性高达合成醛加成产物的95％ee和dr：95：5 。对于以高达98％ee的对映选择性将α-羟基酮添加到β-芳基硝基烯烃中，观察到了非预期的非对映选择性反转。在α-羟基酮的OH基和催化剂的叔氮之间形成内部氢键导致形成刚性的顺式烯胺中间体，这解释了预期的非对映选择性和非常高的ee。
• Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol
  作者：Sebastián Llopis、Teresa García、Ángel Cantín、Alexandra Velty、Urbano Díaz、Avelino Corma

  DOI：10.1039/c8cy01650j

  日期：——

  active chiral moieties along the network. The hybrid material was studied by means of different characterization techniques (TGA, NMR and IR spectroscopy, chemical and elemental analyses, TEM, and textural measurements), verifying the stability and integrity of the asymmetric active sites in the solid. The hybrid material, HybPyr, is an excellent asymmetric heterogeneous and recyclable catalyst for enantioselective

  基于硅质骨架 HybPyr 中包含的吡咯烷单元，合成了一种新型手性介孔杂化材料，并由特定的双甲硅烷基化前体整合到有机-无机结构中。在软合成条件下且在没有复杂的结构导向剂的情况下，氟化物溶胶-凝胶方法可以产生介孔结构，活性手性部分沿网络均匀分布。通过不同的表征技术（TGA、NMR 和 IR 光谱、化学和元素分析、TEM 和结构测量）对杂化材料进行了研究，验证了固体中不对称活性位点的稳定性和完整性。杂化材料 HybPyr 是一种优异的不对称多相且可回收的催化剂，用于线性醛与 β-硝基苯乙烯衍生物的对映选择性迈克尔加成反应，并对反应产物具有高度立体控制。
• A Visible‐Light‐Powered Polymerization Method for the Immobilization of Enantioselective Organocatalysts into Microreactors
  作者：Rico Warias、Daniele Ragno、Alessandro Massi、Detlev Belder

  DOI：10.1002/chem.202002063

  日期：2020.10.15

  A versatile one‐step photopolymerization approach for the immobilization of enantioselective organocatalysts is presented. Chiral organocatalyst‐containing monoliths based on polystyrene divinylbenzene copolymer were generated inside channels of microfluidic chips. Exemplary performance tests were performed for the monolithic Hayashi–Jørgensen catalyst in continuous flow, which showed good results

  提出了一种用于固定对映选择性有机催化剂的通用的一步光聚合方法。在微流控芯片的通道内生成了基于聚苯乙烯二乙烯基苯共聚物的手性有机催化剂整料。对整块Hayashi–Jrrgensen催化剂进行连续流的示例性性能测试，结果表明，就立体选择性和催化剂稳定性而言，在仅消耗最少的试剂和溶剂的情况下，将迈克尔迈克尔加成至硝基烯烃即可。