4-phenylimino-5,5,5-trifluoro-2-pentanone | 846059-46-9

• 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: 4-phenylimino-5,5,5-trifluoro-2-pentanone
• 英文别名: (4E)-5,5,5-Trifluoro-4-(phenylimino)pentan-2-one；5,5,5-trifluoro-4-phenyliminopentan-2-one
• CAS: 846059-46-9
• 化学式: C₁₁H₁₀F₃NO
• 分子量: 229.202
• InChiKey: QKGGKTLFTNJTHK-UHFFFAOYSA-N

物化性质

• 沸点：
  220.6±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三氟乙酰丙酮 、 苯胺 在 乙酸-D3 、 lanthanide(III)chloride heptahydrate 作用下， 生成 4-phenylimino-1,1,1-trifluoro-2-pentanone 、 4-phenylimino-5,5,5-trifluoro-2-pentanone
  参考文献：
  名称：

  A highly regioselective Friedländer reaction mediated by lanthanum chloride

  摘要：

  A highly efficient and regioselective Friedlander reaction of unsymmetrical 1,3-diketones with 2-aminoaryl aldehydes (ketones) is described. The methodology leads to the synthesis of a broad scope of substituted quinolines in high yield and excellent regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.038

文献信息

• Quinoline formation via a modified Combes reaction: examination of kinetics, substituent effects, and mechanistic pathways
  作者：Joseph C. Sloop

  DOI：10.1002/poc.1433

  日期：2009.2

  intermediate consumption and product formation rates. The reaction was found to be first order in both the diketone and aniline. Product regioselectivity and reaction rates were found to be influenced by substituents on the diketones and anilines with rates varying as much as five fold. The consumption rate of key imine and enamine intermediates mirrored quinoline formation rates, in accord with rate determining

  这是首次报道使用19F NMR光谱监测Combes缩合以监测中间消耗和产物生成速率的Combes缩合反应。发现该反应在二酮和苯胺中都是一级的。发现产物的区域选择性和反应速率受二酮和苯胺上取代基的影响，速率变化多达五倍。关键亚胺和烯胺中间体的消耗速率与喹啉形成速率一致，反映出喹啉的形成速率。一个ρ确定该环化的-0.32。尽管反应常数的符号与限速亲电子芳族取代（EAS）一致，但该值很可能是复合值，这是由于亲核加成和EAS步骤中相反的取代基效应所致。提出了支持这些发现的机制细节和反应途径。版权所有©2008 John Wiley＆Sons，Ltd.
• A highly regioselective Friedländer reaction mediated by lanthanum chloride
  作者：Ying Chen、Jinkun Huang、Tsang-Lin Hwang、T.J. Li、Sheng Cui、Johann Chan、Matthew Bio

  DOI：10.1016/j.tetlet.2012.04.038

  日期：2012.6

  A highly efficient and regioselective Friedlander reaction of unsymmetrical 1,3-diketones with 2-aminoaryl aldehydes (ketones) is described. The methodology leads to the synthesis of a broad scope of substituted quinolines in high yield and excellent regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.