2-(2-oxo-1-pyrrolidinyl)butanenitrile

• 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: 2-(2-oxo-1-pyrrolidinyl)butanenitrile
• 英文别名: 2-(2-Oxopyrrolidin-1-yl)butanenitrile
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: WYHCRWKRZDIRRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-1-pyrrolidinyl)butanenitrile 在 硫酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以50%的产率得到左乙拉西坦
  参考文献：
  名称：

  Radiosynthesis of ¹¹C-Levetiracetam: A Potential Marker for PET Imaging of SV2A Expression

  摘要：

  The multistep preparation of C-11-levetiracetam ((CLEV)-C-11) was carried out by a one-pot radiosynthesis with 8.3 +/- 1.6% (n = 8) radiochemical yield in 50 +/- 5.0 min. Briefly, the propionaldehyde was converted to propan-l-imine in situ as labeling precursor by incubation with ammonia. Without further separation, the imine was reacted with C-11-HCN to form C-11-aminonitrile. This crude was then reacted with 4-chlorobutyryl chloride and followed by hydrolysis to yield C-11-LEV after purification by chiral high-performance liquid chromatography (HPLC). Both the radiochemical and enantiomeric purities of C-11-LEV were >98%.

  DOI：

  10.1021/ml500285t
• 作为产物：
  描述：

  (2S)-2-(2-氧代-1-吡咯烷基)丁腈 在 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 以85 %的产率得到2-(2-oxo-1-pyrrolidinyl)butanenitrile
  参考文献：
  名称：

  Pt 催化水合中 Pt-PR2OH 基团攻击配位腈形成非对映选择性和可逆金属环

  摘要：

  通过催化不对称水合反应动力学拆分外消旋腈 CH(Et)(CN)(环-N(CH 2 ) 3 C(O)–)​​ 形成酰胺 CH(Et)(C(O)NH 2 )(环-N(CH 2 ) 3 C(O)–)​​（左乙拉西坦，Keppra）是一种工业生物催化过程。为了开发使用手性金属配合物作为催化剂前体的类似程序，我们研究了各个步骤的机理和选择性。用 AgOTf 和仲膦氧化物 (SPO)处理 Pt(diphos)Cl 2得到含有手性二磷( ( R , R )-FerroLANE 衍生物或 ( S , S )-Et-FerroTANE) 或手性 SPO 互变异构体 (( R )-DMB-SPOPine)。第二当量的 AgOTf 产生双离子 [Pt(diphos)(PR' 2 OH)][OTf] 2 ( 9–12和14 )，具有 Fe-Pt 相互作用，或 [Pt(( S , S )-Et-FerroTANE )(PMe

  DOI：

  10.1021/acs.organomet.3c00483

文献信息

• Method for preparing levetiracetam and intermediates thereof
  申请人：Vitaworks IP, LLC

  公开号：US11384050B1

  公开（公告）日：2022-07-12

  There is disclosed a method for preparing levetiracetam and intermediates from a compound of the formula: wherein CR is selected from the group consisting of cyano, carboxylic acid, carboxamide, alkali carboxylate, alkaline earth metal carboxylate, alkyl carboxylate, and a mixture thereof.

  本发明公开了一种利用式化合物制备左乙拉西坦及中间体的方法： 其中 CR 选自氰基、羧酸、羧酰胺、碱羧酸盐、碱土金属羧酸盐、烷基羧酸盐及其混合物组成的组。
• [EN] CHEMOENZYMATIC PROCESSES FOR PREPARATION OF LEVETIRACETAM<br/>[FR] PROCÉDÉS CHIMIO-ENZYMATIQUE POUR LA PRÉPARATION DU LÉVÉTIRACÉTAM
  申请人：BIOVERDANT INC

  公开号：WO2009009117A2

  公开（公告）日：2009-01-15

  Compounds and processes for preparing intermediates in the synthesis of levetiracetam and precursors of levetiracetam and related compounds are provided. Also provided are processes for the preparation of levetiracetam or a pharmaceutically acceptable salt thereof. Modified nitrile hydratase polypeptides and uses thereof also are provided. Among the modified nitrile hydratase polypeptides provided are those that have altered activities, including altered enantioselectivity.
• [EN] ENANTIOSELECTIVE CHEMO-ENZYMATIC SYNTHESIS OF OPTICALLY ACTIVE AMINO AMIDE COMPOUNDS<br/>[FR] SYNTHÈSE CHIMIO-ENZYMATIQUE ÉNANTIOSÉLECTIVE DE COMPOSÉS AMINO-AMIDES OPTIQUEMENT ACTIFS
  申请人：PHARMAZELL GMBH

  公开号：WO2021214283A1

  公开（公告）日：2021-10-28

  The present invention relates to a novel biocatalytic process for the stereoselective preparation of alpha amino amide compounds catalyzed by NHase enzymes. A further aspect of the invention relates to novel NHase enzymes as well as further improved NHase enzyme mutants, nucleic acid molecules encoding these enzymes, recombinant microorganisms suitable for preparing such enzymes and mutants. Another aspect of the invention relates to a chemo-biocatalytic process for the preparation of lactam compounds comprising the new catalytic process for the preparation of alpha amino amide compounds catalyzed by NHase enzymes, as well as the chemical oxidation of the alpha amino amide by applying certain chemical oxidation catalysts suitable for converting the alpha amino amide under retention of its stereochemical configuration to the respective lactam. The novel chemobiocatalytic process is particularly suited for the synthesis of valuable pharmaceutical compounds, like in particular (S)-Levetiracetam.
• Radiosynthesis of ¹¹C-Levetiracetam: A Potential Marker for PET Imaging of SV2A Expression
  作者：Hancheng Cai、Thomas J. Mangner、Otto Muzik、Ming-Wei Wang、Diane C. Chugani、Harry T. Chugani

  DOI：10.1021/ml500285t

  日期：2014.10.9

  The multistep preparation of C-11-levetiracetam ((CLEV)-C-11) was carried out by a one-pot radiosynthesis with 8.3 +/- 1.6% (n = 8) radiochemical yield in 50 +/- 5.0 min. Briefly, the propionaldehyde was converted to propan-l-imine in situ as labeling precursor by incubation with ammonia. Without further separation, the imine was reacted with C-11-HCN to form C-11-aminonitrile. This crude was then reacted with 4-chlorobutyryl chloride and followed by hydrolysis to yield C-11-LEV after purification by chiral high-performance liquid chromatography (HPLC). Both the radiochemical and enantiomeric purities of C-11-LEV were >98%.
• Diastereoselective and Reversible Metallacycle Formation by Attack of a Pt-PR₂OH Group on a Coordinated Nitrile in Pt-Catalyzed Hydration
  作者：Jorge A. Garduño、Andrew J. Sasser、Hannah J. Sexton、Russell P. Hughes、David S. Glueck、Arnold L. Rheingold

  DOI：10.1021/acs.organomet.3c00483

  日期：2024.2.12

  oxides (SPOs) gave the cations [Pt(diphos)(PR'2OH)(Cl)][OTf] 1–6 containing either a chiral diphos ((R,R)-FerroLANE derivatives or (S,S)-Et-FerroTANE) or a chiral SPO tautomer ((R)-DMB-SPOPine). A second equiv of AgOTf yielded dicationic [Pt(diphos)(PR'2OH)][OTf]2 (9–12 and 14), with Fe–Pt interactions, or [Pt((S,S)-Et-FerroTANE)(PMe2OH)(OTf)][OTf] (13). Pt complexes 9 and 11–14 catalyzed hydration

  通过催化不对称水合反应动力学拆分外消旋腈 CH(Et)(CN)(环-N(CH 2 ) 3 C(O)–)​​ 形成酰胺 CH(Et)(C(O)NH 2 )(环-N(CH 2 ) 3 C(O)–)​​（左乙拉西坦，Keppra）是一种工业生物催化过程。为了开发使用手性金属配合物作为催化剂前体的类似程序，我们研究了各个步骤的机理和选择性。用 AgOTf 和仲膦氧化物 (SPO)处理 Pt(diphos)Cl 2得到含有手性二磷( ( R , R )-FerroLANE 衍生物或 ( S , S )-Et-FerroTANE) 或手性 SPO 互变异构体 (( R )-DMB-SPOPine)。第二当量的 AgOTf 产生双离子 [Pt(diphos)(PR' 2 OH)][OTf] 2 ( 9–12和14 )，具有 Fe-Pt 相互作用，或 [Pt(( S , S )-Et-FerroTANE )(PMe