(2S,3R)-2-benzyl-4-nitro-3-phenylbutanal | 1021394-80-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2S,3R)-2-benzyl-4-nitro-3-phenylbutanal
• 英文别名: 2-benzyl-4-nitro-3-phenylbutanal
• CAS: 1021394-80-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: BSIWIASMKQTUMC-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  苯丙醛 、 反式硝基苯乙烯 在 N-甲基吗啉 、 C₁₆H₂₆N₄O₅ 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以100%的产率得到(2S,3R)-2-benzyl-4-nitro-3-phenylbutanal
  参考文献：
  名称：

  在无溶剂条件下通过Aldol反应-胺催化使仲胺催化剂失活。

  摘要：

  尽管对胺催化的立体选择反应有浓厚的兴趣，但由于反应性低或催化剂失活，≥10mol％的高催化剂负载量仍然很常见。然而，很少有人了解失活途径。在这里，我们通过不良的醛醇缩合反应揭示了仲胺的失活。用肽和脯氨醇甲硅烷基醚催化剂进行的机理研究表明，这种到目前为止尚未充分认识到的催化剂失活途径的普遍性。这些见解使醛和硝基烯烃之间的共轭加成反应在无溶剂的情况下（以对环境无害的方法有吸引力的条件）在数克规模下得以实现，并且在低至0.1 mol％的化学选择性肽催化剂存在下，仍具有出色的产物收率和立体选择性。 。

  DOI：

  10.1021/acs.joc.0c00665

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。
• One-Pot Asymmetric Synthesis of γ-Nitroaldehydes from Aldehydes and Nitroalkanes through a Catalytic Tandem Reaction Using an Amino Acid Lithium Salt
  作者：Masanori Yoshida、Naoki Kitamikado、Hiroto Ikehara、Shoji Hara

  DOI：10.1021/jo102570p

  日期：2011.4.1

  One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.

  从醛和硝基烷烃γ-nitroaldehydes的一锅不对称合成，通过使用一级氨基酸锂盐，催化串联反应实现ø -叔-butyldiphenylsilyl升-酪氨酸锂盐，作为催化剂。各种芳基，烯基和烷基醛通过原位生成硝基烯烃转化为γ-硝基醛。
• Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts
  作者：A. Castán、R. Badorrey、J. A. Gálvez、P. López-Ram-de-Víu、M. D. Díaz-de-Villegas

  DOI：10.1039/c7ob02798b

  日期：——

  the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optimal reaction conditions, these bifunctional organocatalysts showed a high catalytic efficiency (almost quantitative yield in most cases) and stereoselectivity in the Michael addition reactions of a variety

  已经从高烯丙基胺合成了用于羰基化合物不对称迈克尔加成到硝基烯烃的新型双官能吡咯烷基有机催化剂，其很容易从作为手性前体的（R）-甘油醛获得。在最佳反应条件下，这些双功能有机催化剂在多种醛（高达98：2 dr和97％ee）和酮（高达5％）的迈克尔加成反应中显示出高催化效率（在大多数情况下几乎是定量产率）和立体选择性。 98：2 dr和99％ee）转化为硝基烯烃。
• Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
  作者：Alejandro Castán、Ramón Badorrey、José A Gálvez、María D Díaz-de-Villegas

  DOI：10.3762/bjoc.13.59

  日期：——

  pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved

  通过衍生自非对映选择性烯丙基化，随后进行顺序的加氢锆化/碘化反应，由（R）-甘油醛丙酮化物衍生的手性亚胺合成了在C2具有较大取代基的新型吡咯烷基有机催化剂。发现新化合物是醛向硝基烯烃的迈克尔加成反应的有效有机催化剂，对映选择性高达85％ee。
• Enantioselective Michael additions of aldehydes to nitroalkenes catalyzed with ionically tagged organocatalyst
  作者：Radovan Šebesta、Attila Latika

  DOI：10.2478/s11532-013-0391-4

  日期：2014.3.1

  Enantioselective organocatalytic Michael additions affords useful building blocks for many biologically and medicinally relevant compounds. Ionically-tagged diphenylprolinol silyl ether efficiently catalyzes several Michael additions of aldehydes to nitroalkenes in ionic liquids. The Michael additions work well in ionic liquids; yields up to 95% and enantioselectivities up to 95% ee were achieved.

  对映选择性有机催化迈克尔加成物为许多生物学和医学上相关的化合物提供了有用的结构单元。带有离子标记的二苯基脯氨醇甲硅烷基醚可有效催化离子液体中硝基与烯烃之间的几种迈克尔加成反应。迈克尔的添加剂在离子液体中效果很好。收率高达95％，对映选择性高达95％ee。此外，在某些情况下，催化系统是可重复使用的。