1-ethynyl-4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzene | 937701-61-6

• 英文名称: 1-ethynyl-4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzene
• 英文别名: 1-Ethynyl-4-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]benzene
• CAS: 937701-61-6
• 化学式: C₁₄H₁₇FO₃
• 分子量: 252.286
• InChiKey: ZKVQPYWVAPPMON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethynyl-4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzene 、 4-碘苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以58%的产率得到4-[2-[4-[2-[2-(2-Fluoroethoxy)ethoxy]ethoxy]phenyl]ethynyl]phenol
  参考文献：
  名称：

  New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques

  摘要：

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.

  DOI：

  10.1021/jm070090j
• 作为产物：
  描述：

  1-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-4-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 氢氧化钾 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 26.0h， 生成 1-ethynyl-4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzene
  参考文献：
  名称：

  New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques

  摘要：

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.

  DOI：

  10.1021/jm070090j