1-(4-chlorobenzyl)pyrrolidin-2-one | 60737-10-2

• 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-(4-chlorobenzyl)pyrrolidin-2-one
• 英文别名: 1-(4-Chlorobenzyl)-2-pyrrolidinone；1-[(4-chlorophenyl)methyl]pyrrolidin-2-one
• CAS: 60737-10-2
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: HHMICZRJTHFXRX-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±25.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)pyrrolidin-2-one 在 正丁基锂 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.17h， 生成 1-(4-chlorobenzyl)-3-methylenepyrrolidin-2-one
  参考文献：
  名称：

  Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

  摘要：

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.050
• 作为产物：
  描述：

  bis[(4-chlorophenyl)methyl](3-butynyl)amine 在 正丁基锂 、 tetrakis(trifluoroacetato)rhodium(II) 、 水 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 11.0h， 生成 1-(4-chlorobenzyl)pyrrolidin-2-one
  参考文献：
  名称：

  Rh-catalyzed intramolecular debenzylative cyclization of amines. Butyrolactams from benzylamines having a chloroacetylene moiety

  摘要：

  When benzylamines having a chloroacetylene moiety were heated in wet toluene with a catalytic amount of rhodium trifluoroacetate dimer, intramolecular debenzylative cyclization took place to give butyrolactams. This method is a new entry to selective debenzylation of amines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.104

文献信息

• Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with <i>ω</i> ‐Amino Fatty Acids under Hydrosilylation Conditions
  作者：Satawat Tongdee、Duo Wei、Jiajun Wu、Chakkrit Netkaew、Christophe Darcel

  DOI：10.1002/ejoc.202100719

  日期：2021.10.26

  An unprecedented efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids under hydrosilylation conditions was developed leading to the corresponding lactams. A variety of pyrrolidinones, piperidinones, 2-azepanones were prepared in up to 95 % isolated yields (29 examples).

  开发了一种前所未有的有效方法，用于在氢化硅烷化条件下用ω-氨基脂肪酸还原胺化羰基衍生物，从而产生相应的内酰胺。制备了多种吡咯烷酮、哌啶酮、2-氮杂环庚酮，分离产率高达 95%（29 个实施例）。
• Iridium-Catalyzed Single-Step <i>N</i>-Substituted Lactam Synthesis from Lactones and Amines
  作者：Kicheol Kim、Soon Hyeok Hong

  DOI：10.1021/acs.joc.5b00101

  日期：2015.4.17

  Catalytic lactam synthesis was achieved directly from lactones and amines using an Ir catalyst. Three sequential transformations—aminolysis of lactone, N-alkylation of amine with hydroxyamide, and intramolecular transamidation of aminoamide—afforded the corresponding N-substituted lactams.

  使用Ir催化剂可直接由内酯和胺类催化合成内酰胺。三个连续的转化-内酯的氨基分解，胺与羟酰胺的N-烷基化以及氨基酰胺的分子内氨基转移-使相应的N-取代的内酰胺得到满足。
• [EN] NICOTINAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE NICOTINAMIDE
  申请人：PFIZER LTD

  公开号：WO2009153721A1

  公开（公告）日：2009-12-23

  The present invention relates to compounds of the formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are defined herein, to compositions containing such compounds and to the uses of such compounds for the treatment of allergic and respiratory conditions.

  本发明涉及式(I)化合物及其药用可接受的盐和溶剂化物，其中取代基在此处定义，含有此类化合物的组合物，以及使用此类化合物治疗过敏和呼吸系统疾病的用途。
• MULTISUBSTITUTED AROMATIC COMPOUNDS AS SERINE PROTEASE INHIBITORS
  申请人：VERSEON CORPORATION

  公开号：US20160024047A1

  公开（公告）日：2016-01-28

  There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of kallikrein, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing certain diseases or disorders, which disease or disorder is amenable to treatment or prevention by the inhibition of kallikrein.

  本发明提供了多取代芳香化合物，其中包括取代的吡唑基或取代的三唑基，用于抑制卡利肽酶，另外还提供了制药组合物。本发明还提供了治疗和预防某些疾病或疾病的方法，该疾病或疾病可通过抑制卡利肽酶来治疗或预防。
• Multisubstituted aromatic compounds as serine protease inhibitors
  申请人：VERSEON CORPORATION

  公开号：US10058541B2

  公开（公告）日：2018-08-28

  There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of kallikrein, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing certain diseases or disorders, which disease or disorder is amenable to treatment or prevention by the inhibition of kallikrein.

  除其他外，还提供了可用于抑制卡利克林的多取代芳香族化合物，这些化合物包括取代的吡唑基或取代的三唑基。另外还提供了药物组合物。此外，还提供了治疗和预防某些疾病或失调的方法，这些疾病或失调可通过抑制卡利克林来治疗或预防。