1-(2-phenylacetyl)pyrrolidin-2-one | 25083-02-7

• 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: 1-(2-phenylacetyl)pyrrolidin-2-one
• CAS: 25083-02-7
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD00451909
• 分子量: 203.241
• InChiKey: OPKFJWODEXMYNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-phenylacetyl)pyrrolidin-2-one 、 乙烷,三氯氟- 在 二叔丁基过氧化物 、 四丁基碘化铵 作用下， 以 水 为溶剂， 反应 16.0h， 以91%的产率得到N-(4-methylphenyl)-2-phenylacetamide
  参考文献：
  名称：

  苯甲酰吡咯烷-2-酮和胺在水性条件下的无金属转酰胺化

  摘要：

  N-酰基内酰胺酰胺，如苯甲酰吡咯烷-2-酮、苯甲酰哌啶-2-酮和苯甲酰西泮-2-酮在DTBP和TBAI存在下与胺反应，以良好的收率得到转酰胺基产物。该反应在水性条件下进行，并获得了良好的官能团耐受性。脂肪族和芳香族伯胺在无金属条件下均表现出良好的活性。提出了一种自由基反应途径。

  DOI：

  10.1039/d1ob00967b
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 52.0h， 生成 1-(2-phenylacetyl)pyrrolidin-2-one
  参考文献：
  名称：

  The Photochemical Synthesis of N-arylacetyl Lactams

  摘要：

  描述了在含有碳酸钾的丙酮：水混合物中，由吡咯烷和哌啶-2-羧酸的相应 N-苯基乙醛酸衍生物光化学生成 N-芳基乙酰内酰胺的过程。有证据表明，在这一过程中可能会形成和裂解环醚，从而导致羰基的 1，4-转移。

  DOI：

  10.3184/174751913x13594855388300

文献信息

• Process for preparing optically active 4-hydroxy-2-pyrrolidinone and n-substituted 4-hydroxy-2-pyrrolidinones by enzymatic hydroxylation
  申请人：——

  公开号：US20040009562A1

  公开（公告）日：2004-01-15

  This invention provides a process for the preparation of optically active 4-hydroxy-2-pyrrolidinone or N-substituted 4-hydroxy-2-pyrrolidinones, wherein an oxygen atom is inserted regio- and stereoselectively into the corresponding non-hydroxylated 2-pyrrolidinones, by using, as a biocatalyst, a microorganism having hydroxylation activity, or a host-organism having the gene(s) necessary for the hydroxylation enzymes derived from the said microorganism, or an enzyme having hydroxylation activity derived from the above microorganisms. The microorganism may be selected from the group consisting of microorganisms that degrade alkanes or cyclic hydrocarbons, microorganisms having alkane hydroxylase(s), or microorganisms that are able to oxidize hydrocarbons.

  本发明提供了一种制备光学活性4-羟基-2-吡咯烷酮或N-取代的4-羟基-2-吡咯烷酮的方法，其中将氧原子以区域和立体选择性插入相应的非羟基化2-吡咯烷酮中，使用具有羟化活性的微生物或具有来自所述微生物的羟化酶所必需的基因的宿主生物作为生物催化剂，或者使用来自上述微生物的羟化酶活性的酶。微生物可以从降解烷烃或环烃的微生物、具有烷烃羟化酶的微生物或能够氧化碳氢化合物的微生物中选择。
• Ring Opening of <i>N</i>-Acyl Lactams Using Nickel-Catalyzed Transamidation
  作者：Karthik Rajan Rajamanickam、Sunwoo Lee

  DOI：10.1021/acs.joc.3c02486

  日期：2024.1.19

  We successfully developed a nickel-catalyzed transamidation method for the ring opening of N-acyl lactams. The method involves a reaction between N-benzoylpyrrolidin-2-one derivatives and aniline derivatives, with Ni(PPh3)2Cl2 serving as the catalyst, 2,2′-bipyridine as the ligand, and manganese as the reducing agent. This reaction led to the formation of ring-opening-amidated products in good yields

  我们成功开发了镍催化N-酰基内酰胺开环转酰胺基化方法。该方法以Ni(PPh 3 ) 2 Cl 2为催化剂，2，2'-联吡啶为配体，锰为还原剂，由N-苯甲酰吡咯烷-2-酮衍生物与苯胺衍生物反应。该反应以良好的产率形成了开环酰胺化产物。值得注意的是，该方法在生产各种环尺寸的相应开环转酰胺基产物（包括四元环、五元环、六元环、七元环和八元环内酰胺）方面表现出优异的效率。
• Process for preparing optically active 4-hydroxy-2-pyrrolidinone and N-substituted 4-hydroxy-2-pyrrolidinones by enzymatic hydroxylation
  申请人：Eidgenössische Technische Hochschule Zürich

  公开号：EP1197561A1

  公开（公告）日：2002-04-17

  This invention provides a process for the preparation of optically active 4-hydroxy-2-pyrrolidinone or N-substituted 4-hydroxy-2-pyrrolidinones, wherein an oxygen atom is inserted regio- and stereoselectively into the corresponding non-hydroxylated 2-pyrrolidinones, by using, as a biocatalyst, a microorganism having hydroxylation activity, or a host-organism having the gene(s) necessary for the hydroxylation enzymes derived from the said microorganism, or an enzyme having hydroxylation activity derived from the above microorganisms. The microorganism may be selected from the group consisting of microorganisms that degrade alkanes or cyclic hydrocarbons, microorganisms having alkane hydroxylase(s), or microorganisms that are able to oxidize hydrocarbons.

  本发明提供了一种制备具有光学活性的 4-羟基-2-吡咯烷酮或 N-取代的 4-羟基-2-吡咯烷酮的工艺，其中氧原子可在相应的非羟基化 2-吡咯烷酮中进行区域和立体选择性插入、作为生物催化剂，使用具有羟基化活性的微生物，或具有羟基化酶所需基因的宿主生物，或从上述微生物中提取的具有羟基化活性的酶。所述微生物可选自降解烷烃或环烃的微生物、具有烷烃羟化酶的微生物或能够氧化烃的微生物。
• Direct <i>N</i>-Acylation of Lactams, Oxazolidinones, and Imidazolidinones with Aldehydes by Shvo’s Catalyst
  作者：Jian Zhang、Soon Hyeok Hong

  DOI：10.1021/ol302087z

  日期：2012.9.7

  Direct N-acylation of lactams, oxazolidinones, and imidazolidinones was achieved with aldehydes by Shvo's catalyst without using any other stoichiometric reagent. The N-acylations with alpha,beta-unsaturated aldehydes were achieved with excellent yields.
• Synthesis and anticonvulsant activity of 1-acyl-2-pyrrolidinone derivatives
  作者：Hitoshi Sasaki、Yoshiyuki Mori、Junzo Nakamura、Juichiro Shibasaki

  DOI：10.1021/jm00106a025

  日期：1991.2

  Several 1-acyl-2-pyrrolidinone derivatives were synthesized as derivatives of gamma-aminobutyric acid (GABA), and their pharmacological activities and stabilities were investigated. The derivatives showed anticonvulsant effect on picrotoxin-induced seizure at a dose of 200 mg/kg. In particular, 1-decanoyl-2-pyrrolidinone (7) and 1-dodecanoyl-2-pyrrolidinone (8) had a high activity. The anticonvulsant activity showed a dose dependency. Some of 1-acyl-2-pyrrolidinone derivatives prolonged sleeping time which was induced by sodium pentobarbital and showed a recovery from disruption of the memory of passive avoidance response, which was induced by an electroconvulsive shock. As shown by the results of the stability study of 1-acetyl-2-pyrrolidinone (1), it was degraded in an acidic buffer and an alkaline buffer although 2-pyrrolidinone was stable. 1-Acyl-2-pyrrolidinone derivatives were degraded in liver and brain homogenates of mouse and rat. They showed a degradation rate in rat plasma. Conversion of 8 to GABA in mouse liver homogenate was demonstrated. These results suggested that the pharmacological activity of 1-acyl-2-pyrrolidinone is probably due to the release of GABA by hydrolysis of derivatives although further work is necessary.