(2S,3S)-2-benzoyl-N,N-dimethyl-4-nitro-3-phenylbutanamide | 1639156-56-1

• 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,3S)-2-benzoyl-N,N-dimethyl-4-nitro-3-phenylbutanamide
• 英文别名: 2-benzoyl-N,N-dimethyl-4-nitro-3-phenylbutanamide
• CAS: 1639156-56-1
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: KPKITADBVZYNKL-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯甲酸乙酯 在 正丁基锂 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.17h， 生成 (2S,3S)-2-benzoyl-N,N-dimethyl-4-nitro-3-phenylbutanamide
  参考文献：
  名称：

  Creation through Immobilization: A New Family of High Performance Heterogeneous Bifunctional Iminophosphorane (BIMP) Superbase Organocatalysts

  摘要：

  An immobilized chiral bifunctional iminophosphorane superbase organocatalyst has been developed and applied in a range of challenging enantioselective reactions. A unique feature of this novel catalytic system is that the final step creation of the iminophosphorane occurs at the point of immobilization. The utility of the immobilized catalyst system was demonstrated in the nitro-Mannich reaction of ketimines as well as the conjugate addition of high pK(a) 1,3-dicarbonyl pro-nucleophiles to nitrostyrene. Catalyst recycling was also demonstrated.

  DOI：

  10.1021/ol5029942

文献信息

• Organocatalytic Enantio- and Diastereoselective Conjugate Addition to Nitroolefins: When β-Ketoamides Surpass β-Ketoesters
  作者：Haiying Du、Jean Rodriguez、Xavier Bugaut、Thierry Constantieux

  DOI：10.1002/chem.201402192

  日期：2014.7.1

  Our findings on the bifunctional squaramide‐catalyzed enantioselective conjugate addition of β‐ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene β‐ketoamides, unlike the extensively studied β‐ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted

  披露了我们在双官能方酰胺催化的β-酮酰胺对硝基烯烃的对映选择性共轭加成反应中的发现。看起来，与广泛研究的β-酮酸酯不同，简单的无环亚甲基β-酮酰胺提供了极佳的非对映选择性，并保持了高收率和对映选择性。此外，进行竞争和动力学研究以合理化所观察到的反应性和选择性。高水平的非对映异构控制以及酰胺基团对后功能化的适应性，大大提高了转化的合成效用。