(S,Z)-benzyl 2-(2-amino-2-(hydroxyimino)ethyl)pyrrolidine-1-carboxylate | 1166995-46-5

• 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: (S,Z)-benzyl 2-(2-amino-2-(hydroxyimino)ethyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-(2-amino-2-hydroxyiminoethyl)pyrrolidine-1-carboxylate
• CAS: 1166995-46-5
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: LODICYMAAPWRHK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.15
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S,Z)-benzyl 2-(2-amino-2-(hydroxyimino)ethyl)pyrrolidine-1-carboxylate 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以41%的产率得到(S)-benzyl 2-((2-oxo-1,2,3,5-oxathiodiazol-3-yl)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Homoproline Analogues Containing Heterocyclic Rings and Their Activity as Organocatalysts for Michael Reaction

  摘要：

  Two homoproline derivatives containing either the 5-thioxo-1,2,4-oxadiazole or the 2-oxo-1,2,3,5-oxathiodiazole bioisosteric groups, in replacement of the carboxyl group, were synthesized and their catalytic activities in Michael reactions were evaluated. The derivative containing the 5-thioxo-1,2,4-oxadiazole ring outperforms proline in the context of enantioselectivity in the reactions between beta-nitrostyrene and acetone or cyclohexanone, indicating that the conversion of the carboxylic group of homoproline to a bioisosteric heterocyclic ring leads to a superior organocatalyst.

  DOI：

  10.3987/com-08-11620
• 作为产物：
  描述：

  (S)-1-CBZ-2-吡咯烷乙氰 在 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 以58%的产率得到(S,Z)-benzyl 2-(2-amino-2-(hydroxyimino)ethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Homoproline Analogues Containing Heterocyclic Rings and Their Activity as Organocatalysts for Michael Reaction

  摘要：

  Two homoproline derivatives containing either the 5-thioxo-1,2,4-oxadiazole or the 2-oxo-1,2,3,5-oxathiodiazole bioisosteric groups, in replacement of the carboxyl group, were synthesized and their catalytic activities in Michael reactions were evaluated. The derivative containing the 5-thioxo-1,2,4-oxadiazole ring outperforms proline in the context of enantioselectivity in the reactions between beta-nitrostyrene and acetone or cyclohexanone, indicating that the conversion of the carboxylic group of homoproline to a bioisosteric heterocyclic ring leads to a superior organocatalyst.

  DOI：

  10.3987/com-08-11620