(2R,3R)-2-methyl-4-nitro-3-phenylbutanal

• 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,3R)-2-methyl-4-nitro-3-phenylbutanal
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: SYIDIEFUDNJFOV-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  反式硝基苯乙烯 、 丙醛 在 (S)-2-tritylpyrrolidine 作用下， 以 正己烷 为溶剂， 反应 72.0h， 生成 (2R,3R)-2-methyl-4-nitro-3-phenylbutanal 、 (2R,3S)-2-methyl-4-nitro-3-phenylbutyraldehyde
  参考文献：
  名称：

  2-三苯甲基吡咯烷的甲硅烷基修饰类似物：合成及其在不对称有机催化中的应用

  摘要：

  硅基有机催化剂：为了研究催化剂骨架内的硅取代碳的影响，我们开发了（S）-2-三苯基甲硅烷基吡咯烷[（S）-2 ]的有效合成方法。在两个有机催化反应中针对（S）-2与其碳类似物（S）-1的评估得到了计算研究的补充。

  DOI：

  10.1002/chem.201002166

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。
• Effective and recyclable dendritic catalysts for the direct asymmetric Michael addition of aldehydes to nitrostyrenes
  作者：Yawen Li、Xin-Yuan Liu、Gang Zhao

  DOI：10.1016/j.tetasy.2006.07.004

  日期：2006.8

  Direct catalytic enantio- and diastereoselective Michael addition reaction of aldehydes to nitrostyrenes is described using a series of recyclable chiral 2-trimethylsilanyloxy-methyl-pyrrolidine-based dendritic catalysts. Good yields (up to 82%), and high diastereoselectivities (up to syn/anti = 95/5) and enantioselectivities (up to 99% ee) have been obtained.

  使用一系列可循环使用的手性2-三甲基甲硅烷基氧基-甲基-吡咯烷基树枝状催化剂描述了醛与硝基苯乙烯的直接催化对映和非对映选择性迈克尔加成反应。获得了良好的收率（高达82％），高的非对映选择性（高达syn / anti  = 95/5）和对映选择性（高达99％ee）。
• 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。
• Novel Octapeptide as an Asymmetric Catalyst for Michael Reaction in Aqueous Media
  作者：Saadi Bayat、Emilia Abdulmalek、Bimo Ario Tejo、Abu Bakar Salleh、Yahaya M. Normi、Mohd Basyaruddin Abdul Rahman

  DOI：10.1080/00397911.2012.762686

  日期：2013.12.2

  this work, three forms of a novel octapeptide have been evaluated as asymmetric catalysts for the Michael reaction. Low quantity catalyst loading, ecofriendly solvents, and reusability of organocatalyst successfully applied to attain excellent yields and moderate enantioselectivities in the Michael reaction. [Supplementary materials are available for this article. Go to the publisher's online edition

  摘要 在这项工作中，已经评估了三种形式的新型八肽作为迈克尔反应的不对称催化剂。少量催化剂负载、环保溶剂和有机催化剂的可重复使用性成功应用于在迈克尔反应中获得优异的产率和适中的对映选择性。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Asymmetric Organocatalytic Cascade Michael/Michael/Henry Reaction Sequence: Control of All Stereocenters in One Cyclohexane Skeleton
  作者：Zhifeng Mao、Yaomei Jia、Zhaoqing Xu、Rui Wang

  DOI：10.1002/adsc.201200008

  日期：2012.5.21

  The highly diastereo‐ and enantioselective relay cascade Michael/Michael/Henry reaction catalyzed by combination of readily available diphenylprolinol silyl ether and the quinine thiourea in a one‐pot fashion has been developed. Up to 70% yield and up to >99% enantioselectivity of the single major isomer were obtained from the cascade reactions.

  已经开发出了一种高非对映选择性和对映选择性中继级联Michael / Michael / Henry反应，该反应通过容易获得的二苯基脯氨醇甲硅烷基醚和奎宁硫脲的单锅法进行催化。从级联反应中获得了单一主要异构体的最高70％的收率和最高> 99％的对映选择性。