3-(4-甲氧苯亚甲基)吡咯烷-2-酮 | 1859-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-甲氧苯亚甲基)吡咯烷-2-酮
• 英文名称: (E)-3-(4-methoxybenzylidene)pyrrolidin-2-one
• 英文别名: (E)-3-anisylidenepyrrolidin-2-one；2-Pyrrolidinone, 3-[(4-methoxyphenyl)methylene]-；(3E)-3-[(4-methoxyphenyl)methylidene]pyrrolidin-2-one
• CAS: 1859-45-6
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: PBERPURCNYNNSA-CSKARUKUSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  450.3±45.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧苯亚甲基)吡咯烷-2-酮 、 2-重氮丙烷 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到4-anisyl-3,3-dimethyl-1,2,7-triazaspiro[4.4]non-1-ene-6-one
  参考文献：
  名称：

  新型螺-Δ1-吡唑啉的合成与化学

  摘要：

  在螺环杂环的合成和化学探索中，我们发现2-重氮丙烷与（E）-α-亚芳基吡咯啉-2-酮，（E）-α-亚芳基-γ-丁内酯和（E）-亚芳基-萘酮的反应ñ -arylsuccinimide衍生物产生螺-Δ 1个-pyrazolines。Δ的光解1 -pyrazolines导致环丙烷。所获得的加合物的结构已经通过光谱测量确定。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.827
• 作为产物：
  描述：

  1-乙酰-2-吡咯烷酮 、 4-甲氧基苯甲醛 在 sodium hydride 作用下， 生成 3-(4-甲氧苯亚甲基)吡咯烷-2-酮
  参考文献：
  名称：

  Synthesis of lactams with potential cardiotonic activity

  摘要：

  DOI：

  10.1016/0223-5234(93)90118-x

文献信息

• Iridium‐Catalyzed Highly Enantioselective Hydrogenation of Exocyclic α,β‐Unsaturated Carbonyl Compounds
  作者：Fengtao Tian、Dongmei Yao、Yuanyuan Liu、Fang Xie、Wanbin Zhang

  DOI：10.1002/adsc.201000185

  日期：2010.10.9

  By using the iridium complex of a phosphine-oxazoline ligand with an axis-unfixed biphenyl backbone, a highly enantioselective hydrogenation of the CC bond of exocyclic α,β-unsaturated carbonyl compounds to afford α-chiral cyclic ketones, lactones and lactams was developed.

  通过使用膦-恶唑啉配体的铱配合物和未固定轴联苯骨架，开发了环外α，β-不饱和羰基化合物的CC键的高度对映选择性氢化，从而提供了α-手性环酮，内酯和内酰胺。
• Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
  作者：Wang Delong、Wang Lanying、Wu Yongling、Song Shuang、Feng Juntao、Zhang Xing

  DOI：10.1016/j.ejmech.2017.02.050

  日期：2017.4

  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.
• ORITO KAZUHIKO; MATSUZAKI TSUTOMI, XOKKAJDO DAJGAKU KOGAKUBU KEHNKYU XOKOKU, BULL. FAS. ENG. HOKKAIDO UNIV.,+
  作者：ORITO KAZUHIKO、 MATSUZAKI TSUTOMI

  DOI：——

  日期：——
• Andreani A., Rambaldi M., Locatelli A., Leoni A., Bossa R., Chiericozzi M+, Eur. J. Med. Chem, 28 (1993) N 10, S 825-829
  作者：Andreani A., Rambaldi M., Locatelli A., Leoni A., Bossa R., Chiericozzi M+

  DOI：——

  日期：——
• Synthesis of lactams with potential cardiotonic activity
  作者：A Andreani、M Rambaldi、A Locatelli、A Leoni、R Bossa、M Chiericozzi、I Galatulas、G Salvatore

  DOI：10.1016/0223-5234(93)90118-x

  日期：1993.1