(2S,3S)-methyl 3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-4-nitrobutanoate | 1394134-02-1

• 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: (2S,3S)-methyl 3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-4-nitrobutanoate
• 英文别名: methyl (2S,3S)-2-(benzhydrylideneamino)-3-(4-chlorophenyl)-4-nitrobutanoate
• CAS: 1394134-02-1
• 化学式: C₂₄H₂₁ClN₂O₄
• 分子量: 436.895
• InChiKey: UFBJFDNFHVVKLE-GGAORHGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-nitro-2-(4-chlorophenyl)ethylene 、 二苯亚甲基甘氨酸甲酯 在 C₃₆H₃₆FeN₃PS⁽²⁺⁾ 、 silver(I) acetate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以93%的产率得到(2S,3S)-methyl 3-(4-chlorophenyl)-2-(diphenylmethyleneamino)-4-nitrobutanoate
  参考文献：
  名称：

  Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes

  摘要：

  We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-alpha-imino-gamma-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 degrees C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.

  DOI：

  10.1021/ol301916t

文献信息

• Mild Michael Addition of Glycine Imines to Aromatic Nitroalkenes Catalyzed by DBU with LiOTf as an Additive
  作者：Da-Ming Du、Wei Li、Han Liu

  DOI：10.1055/s-0028-1088210

  日期：2009.4

  A mild Michael addition of glycine imines to aromaticnitroalkenes catalyzed by 10 mol% DBU with LiOTf as an additive was developed. In most cases, the products could be obtained in good yields (up to 96%) with moderate to good diastereoselectivities (up to 10:1). The selectivity for syn adduct can be reversed to anti when the R group of glycine imines was changed from methyl or ethyl to tert-butyl.

  开发了一种温和的迈克尔加成反应，使用10 mol%的DBU催化甘氨酸亚胺与芳香硝基烯烃的反应，并加入LiOTf作为添加剂。在大多数情况下，产物的得率良好（最高可达96%），并且具有中等到良好的非对映选择性（最高可达10:1）。当甘氨酸亚胺的R基团从甲基或乙基变为叔丁基时，顺式加成产物的选择性可以逆转为反式。