3-(4-(dimethylamino)phenyl)-1-(4-fluorophenyl)-2-propyn-1-one | 1258458-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-(dimethylamino)phenyl)-1-(4-fluorophenyl)-2-propyn-1-one
• 英文别名: 3-(4-dimethylaminophenyl)-1-(4-fluorophenyl)prop-2-yn-1-one；3-(4-(Dimethylamino)phenyl)-1-(4-fruorophenyl)-2-propyn-1-one；3-[4-(dimethylamino)phenyl]-1-(4-fluorophenyl)prop-2-yn-1-one
• CAS: 1258458-36-4
• 化学式: C₁₇H₁₄FNO
• 分子量: 267.303
• InChiKey: OJLRUEDATLSQLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氟苯甲酰氯 、 4-二甲基氨基苯乙炔 在 palladium diacetate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以35.2%的产率得到3-(4-(dimethylamino)phenyl)-1-(4-fluorophenyl)-2-propyn-1-one
  参考文献：
  名称：

  Diphenylpropynone derivatives as probes for imaging β-amyloid plaques in Alzheimer’s brains

  摘要：

  A new series of diphenylpropynone (DPP) derivatives for use in vivo to image beta-amyloid (A beta) plaques in the brain of patients with Alzheimer's disease (AD) were synthesized and characterized. Binding experiments in vitro revealed high affinity for A beta (1-42) aggregates at a K(i) value ranging from 6 to 326 nM. Furthermore, specific labeling of plaques was observed in sections of brain tissue from Tg2576 transgenic mice stained using one of the compounds, 1. In biodistribution experiments with normal mice, [(125)I]1displayed moderate uptake (1.55% ID/g at 2 min) and clearance from the brain with time (0.76 ID/g at 60 min). Taken together, DPP can serve as a new molecular scaffold for developing novel A beta imaging agents by introducing appropriate substituted groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.058

文献信息

• A General and Convenient Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides
  作者：Xiao-Feng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201001864

  日期：2010.10.25

  Convenient carbonylations: An efficient methodology for the carbonylative Sonogashira reaction of aryl bromides has been developed (see scheme). Contrary to known procedures, inexpensive aryl bromides can be applied as substrates to give the desired compounds in moderate to good yields (47–88 %).

  方便的羰基化：已开发出一种有效的方法用于芳基溴的羰基化Sonogashira反应（请参见方案）。与已知方法相反，廉价的芳基溴化物可以用作底物，以中等至良好的收率（47–88％）得到所需化合物。
• Diphenylpropynone derivatives as probes for imaging β-amyloid plaques in Alzheimer’s brains
  作者：Masahiro Ono、Hiroyuki Watanabe、Rumi Watanabe、Mamoru Haratake、Morio Nakayama、Hideo Saji

  DOI：10.1016/j.bmcl.2010.11.058

  日期：2011.1

  A new series of diphenylpropynone (DPP) derivatives for use in vivo to image beta-amyloid (A beta) plaques in the brain of patients with Alzheimer's disease (AD) were synthesized and characterized. Binding experiments in vitro revealed high affinity for A beta (1-42) aggregates at a K(i) value ranging from 6 to 326 nM. Furthermore, specific labeling of plaques was observed in sections of brain tissue from Tg2576 transgenic mice stained using one of the compounds, 1. In biodistribution experiments with normal mice, [(125)I]1displayed moderate uptake (1.55% ID/g at 2 min) and clearance from the brain with time (0.76 ID/g at 60 min). Taken together, DPP can serve as a new molecular scaffold for developing novel A beta imaging agents by introducing appropriate substituted groups. (C) 2010 Elsevier Ltd. All rights reserved.