2-[(tert-butyldiphenylsilyl)oxy]-1,4-dimethylphenol | 911381-80-1

• 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-[(tert-butyldiphenylsilyl)oxy]-1,4-dimethylphenol
• 英文别名: Tert-butyl-(2,5-dimethylphenoxy)-diphenylsilane
• CAS: 911381-80-1
• 化学式: C₂₄H₂₈OSi
• 分子量: 360.571
• InChiKey: ZHHMKIBUOIZLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(tert-butyldiphenylsilyl)oxy]-1,4-dimethylphenol 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 48.33h， 生成
  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：

  2,5-二甲基苯酚 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以87.9%的产率得到2-[(tert-butyldiphenylsilyl)oxy]-1,4-dimethylphenol
  参考文献：
  名称：

  18F-FESB：用于β-淀粉样斑块的新型 18F 标记宠物示踪剂的合成和自动放射性氟化

  摘要：

  1-(2'-[18F]-氟乙氧基)-2,5-双(4'-甲氧基苯乙烯基)苯 (18F-FESB) 的合成率约为 76%（比活性 >58.6 GBq 或 1.58 Ci/µmol）在 Advanced Cyclotron Systems 的自动合成装置中，通过 1-(2'-甲苯磺酰乙氧基)-2,5-双(4'-甲氧基苯乙烯基)苯的亲核取代，并使用反相柱色谱纯化。当在离子流体存在下进行时，1-丁基-3-甲基咪唑鎓四氟硼酸盐（Bmim四氟硼酸盐；BmimBF4）或 1-乙基-3-甲基咪唑鎓三氟甲磺酸盐（Emimtriflate；EmimTFMS），18F-FESB 的放射化学产率范围为 17% 到 76% . 在没有这些离子流体的情况下，放射化学产率始终较低（~3-7%）。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1011

文献信息

• 18F-FESB: synthesis and automated radiofluorination of a novel18F-labeled pet tracer forβ-amyloid plaques
  作者：Piyush Kumar、Weizhong Zheng、Stephen A. McQuarrie、Jack H. Jhamandas、Leonard I. Wiebe

  DOI：10.1002/jlcr.1011

  日期：2005.11

  1-(2′-[18F]-fluoroethoxy)-2,5-bis(4′-methoxystyryl)benzene (18F-FESB) was synthesized in ∼76% radiochemical yield (specific activity >58.6 GBq or 1.58 Ci/µmol) in an Advanced Cyclotron Systems' automated synthesis unit by nucleophilic substitution of 1-(2′-toluenesulfonylethoxy)-2,5-bis(4′-methoxystyryl)benzene and purified using reversed phase column chromatography. When performed in the presence

  1-(2'-[18F]-氟乙氧基)-2,5-双(4'-甲氧基苯乙烯基)苯 (18F-FESB) 的合成率约为 76%（比活性 >58.6 GBq 或 1.58 Ci/µmol）在 Advanced Cyclotron Systems 的自动合成装置中，通过 1-(2'-甲苯磺酰乙氧基)-2,5-双(4'-甲氧基苯乙烯基)苯的亲核取代，并使用反相柱色谱纯化。当在离子流体存在下进行时，1-丁基-3-甲基咪唑鎓四氟硼酸盐（Bmim四氟硼酸盐；BmimBF4）或 1-乙基-3-甲基咪唑鎓三氟甲磺酸盐（Emimtriflate；EmimTFMS），18F-FESB 的放射化学产率范围为 17% 到 76% . 在没有这些离子流体的情况下，放射化学产率始终较低（~3-7%）。版权所有 © 2005 John Wiley & Sons, Ltd.
• Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands
  作者：Rob J.A. Nabuurs、Varsha V. Kapoerchan、Athanasios Metaxas、Sanne de Jongh、Maaike de Backer、Mick M. Welling、Wim Jiskoot、Albert D. Windhorst、Hermen S. Overkleeft、Mark A. van Buchem、Mark Overhand、Louise van der Weerd

  DOI：10.1016/j.bmc.2014.02.054

  日期：2014.4

  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.