5-(4-Methoxyphenyl)-1-methyl-3-methylidenepyrrolidin-2-one | 1037575-86-2

• 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: 5-(4-Methoxyphenyl)-1-methyl-3-methylidenepyrrolidin-2-one
• CAS: 1037575-86-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: VPABOJRORKZEPO-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  384.5±42.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  哌啶 、 5-(4-Methoxyphenyl)-1-methyl-3-methylidenepyrrolidin-2-one 反应 2.0h， 生成 (3R,5S)-5-(4-methoxyphenyl)-1-methyl-3-(piperidin-1-ylmethyl)pyrrolidin-2-one 、
  参考文献：
  名称：

  Gamma-lactams—A novel scaffold for highly potent and selective α7 nicotinic acetylcholine receptor agonists

  摘要：

  A novel class of alpha 7 nicotinic acetylcholine receptor (nAChR) agonists has been discovered through high-throughput screening. The cis gamma-lactam scaffold has been optimized to reveal highly potent and selective alpha 7 nAChR agonists with in vitro activity and selectivity and with good brain penetration in mice. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.073
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 、 N-(4-甲氧基亚苄基)甲胺 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 生成 5-(4-Methoxyphenyl)-1-methyl-3-methylidenepyrrolidin-2-one
  参考文献：
  名称：

  Gamma-lactams—A novel scaffold for highly potent and selective α7 nicotinic acetylcholine receptor agonists

  摘要：

  A novel class of alpha 7 nicotinic acetylcholine receptor (nAChR) agonists has been discovered through high-throughput screening. The cis gamma-lactam scaffold has been optimized to reveal highly potent and selective alpha 7 nAChR agonists with in vitro activity and selectivity and with good brain penetration in mice. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.073

文献信息

• Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams
  作者：Anna Albrecht、Jacek F. Koszuk、Jakub Modranka、Marek Różalski、Urszula Krajewska、Anna Janecka、Kazimierz Studzian、Tomasz Janecki

  DOI：10.1016/j.bmc.2008.03.035

  日期：2008.5

  A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a-g'' and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a-c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a-g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner-Wadsworth-Emmons olefination of aldehydes using

  从4开始合成了一系列5-芳基-3-亚烷基二烯基二氢呋喃-2（3H）-酮6a-g''和11a，b以及5-芳基-3-亚甲基亚吡咯烷酮-2-酮10a-c和12。 -芳基-2-二乙氧基磷酰基-4-氧代丁酸酯3a-g。反应顺序包括羰基的还原或还原胺化，内酯化或内酰胺化步骤，最后使用由此获得的5-芳基-3-二乙氧基磷酰基-3,4-二氢呋喃-2（5H）-进行醛的霍纳-沃兹沃思-埃蒙斯烯化反应。 5a-g''或5-芳基-3-二乙氧基磷酰基吡咯烷二-2-酮9a-c。在体外评估了呋喃酮6和11以及吡咯烷酮10和12对小鼠白血病细胞系L-1210和两种人白血病细胞系HL-60和NALM-6的抗性。事实证明，所获得的几种呋喃酮对所有三种细胞系的IC（50）值均低于6 microM都非常有效。
• Gamma-lactams—A novel scaffold for highly potent and selective α7 nicotinic acetylcholine receptor agonists
  作者：Albert Enz、Dominik Feuerbach、Mathias U. Frederiksen、Conrad Gentsch、Konstanze Hurth、Werner Müller、Joachim Nozulak、Bernard L. Roy

  DOI：10.1016/j.bmcl.2009.01.073

  日期：2009.3

  A novel class of alpha 7 nicotinic acetylcholine receptor (nAChR) agonists has been discovered through high-throughput screening. The cis gamma-lactam scaffold has been optimized to reveal highly potent and selective alpha 7 nAChR agonists with in vitro activity and selectivity and with good brain penetration in mice. (C) 2009 Elsevier Ltd. All rights reserved.