ethyl 3-azido-2-((4-methoxyphenyl)amino)-4-oxohexanoate | 1004750-75-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-azido-2-((4-methoxyphenyl)amino)-4-oxohexanoate
• CAS: 1004750-75-7
• 化学式: C₁₅H₂₀N₄O₄
• 分子量: 320.348
• InChiKey: GTRWJXGBONRNLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  113.39
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-azido-butan-2-one 、 Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 在 (R)-吡咯烷-3-羧酸 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 ethyl (2S,3R)-3-azido-2-(p-methoxyphenylamino)-4-oxohexanoate 、 ethyl 3-azido-2-(4-methoxyphenylamino)-4-oxohexanoate 、 ethyl 3-azido-2-((4-methoxyphenyl)amino)-4-oxohexanoate
  参考文献：
  名称：

  Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions:  Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

  摘要：

  The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with a-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.

  DOI：

  10.1021/ja074907+