1-(三氟乙酰基)-2-吡咯烷酮 | 94363-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(三氟乙酰基)-2-吡咯烷酮
• 英文名称: 1-(trifluoroacetyl)-2-pyrrolidinone
• 英文别名: 1-(2,2,2-trifluoroacetyl)pyrrolidin-2-one
• CAS: 94363-57-2
• 化学式: C₆H₆F₃NO₂
• 分子量: 181.114
• InChiKey: FQHOKIFYABLFQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-(三氟乙酰基)-2-吡咯烷酮 、 4-丁氧基苯甲醛 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (E)-3-(4-butoxybenzylidene)pyrrolidin-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：

  2-吡咯烷酮 、 三氟乙酸酐 以 甲苯 为溶剂， 反应 1.0h， 生成 1-(三氟乙酰基)-2-吡咯烷酮
  参考文献：
  名称：

  SpinPhox /铱（I）催化的环状α-亚烷基羰基化合物的不对称加氢

  摘要：

  带有α-手性碳中心的旋光中型环状羰基化合物在制药科学和不对称合成中引起人们的兴趣。在本文中，SpinPhox / Ir I催化剂在环外α，β-不饱和环状羰基化合物（包括各种α-亚烷基内酰胺，不饱和环状酮）中的CC键的不对称氢化中被证明具有高度对映选择性。内酯。值得注意的是，该方法可以成功地用于具有六元或七元环的具有挑战性的α-烷基亚内酰胺底物的不对称氢化，从而提供相应的具有α-手性碳中心的旋光羰基化合物，其对映体过量通常非常好（高达ee的98％ ）。该协议的合成用途还已在抗炎药洛索洛芬及其类似物以及生物学上重要的ε-氨基己酸衍生物的不对称合成中得到证明。

  DOI：

  10.1002/anie.201309521

文献信息

• ORGANIC COMPOUNDS
  申请人：Dales Natalie

  公开号：US20100029718A1

  公开（公告）日：2010-02-04

  The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。本发明还涵盖使用这种衍生物来调节硬脂酰辅酶A去饱和酶活性的方法和包含这种衍生物的制药组合物。
• Heterocyclic inhibitors of stearoyl-CoA desaturase
  申请人：Novartis AG

  公开号：US08236835B2

  公开（公告）日：2012-08-07

  The present invention provides heterocyclic derivatives that modulate the activity of stearoyl-CoA desaturase. Methods of using such derivatives to modulate the activity of stearoyl-CoA desaturase and pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了能够调节硬脂酰辅酶A去饱和酶活性的杂环衍生物。该发明还涵盖了使用这些衍生物来调节硬脂酰辅酶A去饱和酶活性的方法，以及包含这些衍生物的药物组合物。
• WO2008/36715
  申请人：——

  公开号：——

  公开（公告）日：——
• Kramarova, E. P.; Shipov, A. G.; Artamkina, O. B., Journal of general chemistry of the USSR, 1984, vol. 54, # 8, p. 1712 - 1713
  作者：Kramarova, E. P.、Shipov, A. G.、Artamkina, O. B.、Baukov, Yu. I.

  DOI：——

  日期：——
• KRAMAROVA, E. P.;SHIPOV, A. G.;ARTAMKINA, O. B.;BAUKOV, YU. I., ZH. OBSHCH. XIMII, 1984, 54, N 8, 1921-1922
  作者：KRAMAROVA, E. P.、SHIPOV, A. G.、ARTAMKINA, O. B.、BAUKOV, YU. I.

  DOI：——

  日期：——