2-(2,5-difluorophenyl)-2-oxazoline

• 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: 2-(2,5-difluorophenyl)-2-oxazoline
• 英文别名: 2-(2,5-Difluorophenyl)-4,5-dihydro-1,3-oxazole；2-(2,5-difluorophenyl)-4,5-dihydro-1,3-oxazole
• 化学式: C₉H₇F₂NO
• 分子量: 183.157
• InChiKey: XGUIOJITUUALEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,5-difluorophenyl)-2-oxazoline 在 palladium on activated charcoal nickel(IV) oxide 、 正丁基锂 、 氢气 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 51.5h， 生成 3-[4-(4-Fluoro-2-oxazol-2-yl-phenyl)-piperazin-1-yl]-propylamine
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j
• 作为产物：
  描述：

  N-(2-chloroethyl)-2-(2,5-difluorophenyl)acid amide 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 以54%的产率得到2-(2,5-difluorophenyl)-2-oxazoline
  参考文献：
  名称：

  氟化2-苯基-2-恶唑啉的合成，微波辅助聚合和聚合物性能：系统研究。

  摘要：

  我们目前对氟化2-苯基-2-恶唑啉的合成及其进行聚合的能力进行详细的系统研究。这些化合物的合成是基于两步法进行的，该过程以中等至良好的产率提供了所需的2-恶唑啉。所有化合物均通过IR和NMR（（1）H，（13）C和（19）F）光谱，质谱和元素分析充分表征。随后将2-恶唑啉用作活性阳离子开环聚合（CROP）的单体，微波辐射为热源（T = 140摄氏度），硝基甲烷为溶剂，甲苯磺酸甲酯为引发剂。聚合反应的线性一阶动力学图伴随分子量随转化率和低多分散指数（PDI）值（通常低于1）线性增加。30）表示活性聚合机理。所得的聚合速率通常反映出对氟取代基的量特别是苯环的邻氟取代基的存在或不存在的强烈敏感性。分离所有聚合物并通过尺寸排阻色谱法和MALDI-TOF质谱法表征。最后，通过使用差示扫描量热法，热重分析和接触角测量对选定的聚合物性能进行了详细研究，从而得出了结构-性质关系。尽管聚合物的热性质主要受邻

  DOI：

  10.1002/chem.200800671

文献信息

• <i>N-</i>Arylpiperazinyl-<i>N</i>‘<i>-</i>propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists
  作者：Todd R. Elworthy、Anthony P. D. W. Ford、Gary W. Bantle、David J. Morgans,、Rachel S. Ozer、Wylie S. Palmer、David B. Repke、Magarita Romero、Leticia Sandoval、Eric B. Sjogren、Francisco X. Talamás、Alfredo Vazquez、Helen Wu、Nicolas F. Arredondo、David R. Blue,、Andrea DeSousa、Lisa M. Gross、M. Shannon Kava、John D. Lesnick、Rachel L. Vimont、Timothy J. Williams、Quan-Ming Zhu、Jürg R. Pfister、David E. Clarke

  DOI：10.1021/jm970166j

  日期：1997.8.1

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.
• Synthesis, Microwave-Assisted Polymerization, and Polymer Properties of Fluorinated 2-Phenyl-2-oxazolines: A Systematic Study
  作者：Matthias Lobert、Hanneke M. L. Thijs、Tina Erdmenger、Rebecca Eckardt、Christoph Ulbricht、Richard Hoogenboom、Ulrich S. Schubert

  DOI：10.1002/chem.200800671

  日期：2008.11.17

  present a detailed systematic study of the synthesis and ability of fluorinated 2-phenyl-2-oxazolines to undergo polymerization. The synthesis of these compounds is based on a two-step procedure that gives the desired 2-oxazolines in moderate-to-good yields. All the compounds were fully characterized by IR and NMR ((1)H, (13)C, and (19)F) spectroscopy, mass spectrometry, and elemental analysis. The

  我们目前对氟化2-苯基-2-恶唑啉的合成及其进行聚合的能力进行详细的系统研究。这些化合物的合成是基于两步法进行的，该过程以中等至良好的产率提供了所需的2-恶唑啉。所有化合物均通过IR和NMR（（1）H，（13）C和（19）F）光谱，质谱和元素分析充分表征。随后将2-恶唑啉用作活性阳离子开环聚合（CROP）的单体，微波辐射为热源（T = 140摄氏度），硝基甲烷为溶剂，甲苯磺酸甲酯为引发剂。聚合反应的线性一阶动力学图伴随分子量随转化率和低多分散指数（PDI）值（通常低于1）线性增加。30）表示活性聚合机理。所得的聚合速率通常反映出对氟取代基的量特别是苯环的邻氟取代基的存在或不存在的强烈敏感性。分离所有聚合物并通过尺寸排阻色谱法和MALDI-TOF质谱法表征。最后，通过使用差示扫描量热法，热重分析和接触角测量对选定的聚合物性能进行了详细研究，从而得出了结构-性质关系。尽管聚合物的热性质主要受邻