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.
• Polysulfonate supported chiral diamine-nickel catalysts: Synthesis and applications
  作者：Jing-xuan Zhou、Dong-yu Zhu、Jie Chen、Xue-jing Zhang、Ming Yan、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2020.152792

  日期：2021.2

  A series of chiral polysulfonate cyclohexyldiamine-Ni(II) catalysts were prepared via sulfur (VI) fluoride exchange click-reactions. The catalysts exhibited good catalytic activity and enantioselectivity in the Michael addition of malonates to nitroalkenes. The excellent recyclability of the catalysts was demonstrated via the reuse of the privileged catalyst 7a for ten times. The results provide a

  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。
• Enantioselective synthesis of γ-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes
  作者：A. N. Reznikov、E. V. Golovin、Yu. N. Klimochkin

  DOI：10.1134/s1070428013050047

  日期：2013.5

  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.