ethyl (4R)-2-oxo-4-phenylpyrrolidine-3-carboxylate | 1443453-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl (4R)-2-oxo-4-phenylpyrrolidine-3-carboxylate
• CAS: 1443453-37-9
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: QVGUCCHRJMBKNX-VUWPPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (4R)-2-oxo-4-phenylpyrrolidine-3-carboxylate 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 ethyl [(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetate
  参考文献：
  名称：

  Enantioselective synthesis of γ-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes

  摘要：

  A new synthetic approach to (3R)-4-amino-3-methylbutyric acid and [(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide [(R)-phenotropil] has been developed. Asymmetric center with a required configuration has been generated via enantioselective addition of diethyl malonate to 1-nitropropene and beta-nitrostyrene, catalyzed by Ni(II) complexes with (R,R)- and (S,S)-N,N'-dibenzylcyclohexane-1,2-diamine.

  DOI：

  10.1134/s1070428013050047
• 作为产物：
  描述：

  (R)-1,3-diethyl 2-(2-nitro-1-phenylethyl)malonate 在 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 12.0h， 以92%的产率得到ethyl (4R)-2-oxo-4-phenylpyrrolidine-3-carboxylate
  参考文献：
  名称：

  聚磺酸盐负载的手性二胺镍催化剂：合成与应用

  摘要：

  通过氟化硫（VI）交换点击反应制备了一系列手性聚磺酸盐环己基二胺-Ni（II）催化剂。在丙二酸酯向硝基链烯的迈克尔加成中，催化剂表现出良好的催化活性和对映选择性。通过将特权催化剂7a再利用十次，证明了催化剂的优异的再循环性。结果为手性均相催化剂的固定化提供了新的策略。

  DOI：

  10.1016/j.tetlet.2020.152792

文献信息

• BIFUNCTIONAL CHIRAL ORGANOCATALYTIC COMPOUND HAVING EXCELLENT ENANTIOSELECTIVITY, PREPARATION METHOD THEREFOR, AND METHOD FOR PRODUCING NON-NATURAL GAMMA-AMINO ACID FROM NITRO COMPOUND BY USING SAME
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US20200406243A1

  公开（公告）日：2020-12-31

  The present invention relates to a bifunctional chiral organocatalytic compound having excellent enantioselectivity, a preparation method therefor, and a method for producing a non-natural gamma amino acid from a nitro compound by using the chiral organocatalytic compound. According to the present invention, the bifunctional chiral organocatalytic compound having excellent enantioselectivity can be easily synthesized, gamma-amino acids with high optical selectivity can be obtained at a high yield by an economical and convenient method using the chiral organocatalytic compound, and various (R)-configuration gamma-amino acids, which are not present in nature, can be produced with high optical purity in large quantities by using a small amount of a catalyst, and therefore, the present invention can be widely utilized in various industrial fields including the pharmaceutical industry.