tetraethyl ((2-(4,4,4-trifluorobutoxy)-1,4-phenylene)bis(methylene))bis(phosphonate) | 1601462-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tetraethyl ((2-(4,4,4-trifluorobutoxy)-1,4-phenylene)bis(methylene))bis(phosphonate)
• CAS: 1601462-27-4
• 化学式: C₂₀H₃₃F₃O₇P₂
• 分子量: 504.421
• InChiKey: NNECWFMXMLFVTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  32.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tetraethyl ((2-(4,4,4-trifluorobutoxy)-1,4-phenylene)bis(methylene))bis(phosphonate) 、 4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 potassium tert-butylate 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 32.33h， 生成 (E,E)-1-(4,4,4-trifluorobutoxy)-2,5-bis(4-hydroxy)styrylbenzene
  参考文献：
  名称：

  Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands

  摘要：

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential A beta imaging agents. To further explore their potency as F-19 MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Ab plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem F-19 NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.02.054
• 作为产物：
  描述：

  1,4-Dimethyl-2-(4,4,4-trifluorobutoxy)benzene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 32.0h， 生成 tetraethyl ((2-(4,4,4-trifluorobutoxy)-1,4-phenylene)bis(methylene))bis(phosphonate)
  参考文献：
  名称：

  Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands

  摘要：

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential A beta imaging agents. To further explore their potency as F-19 MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-beta binding characteristics. The compounds showed a high affinity for Ab plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem F-19 NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.02.054