potassium (4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)phenyl)trifluoroborate | 1572536-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: potassium (4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)phenyl)trifluoroborate
• CAS: 1572536-55-0
• 化学式: C₂₃H₂₇BF₃*K
• 分子量: 410.372
• InChiKey: HLUOOLYWGZUZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  potassium (4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)phenyl)trifluoroborate 、 [11C]二氧化碳 在 噻吩-2-甲酸亚铜(I) 、 四甲基乙二胺 、 四丁基二氟三苯硅酸铵 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.08h， 以88%的产率得到[¹¹C]bexarotene
  参考文献：
  名称：

  Synthesis of [¹¹C]Bexarotene by Cu-Mediated [¹¹C]Carbon Dioxide Fixation and Preliminary PET Imaging

  摘要：

  Bexarotene (Targretin) is a retinoid X receptor (RXR) agonist that has applications for treatment of T cell lymphoma and proposed mechanisms of action in Alzheimer's disease that have been the subject of recent controversy. Carbon-11 labeled bexarotene ([11C_ carbony1]4-[1-(3,5,5,8,8-pentamethylietralin-2-yOethenyllbenzoic acid) was synthesized using a Cu-mediated cross-coupling reaction employing an arylboronate precursor 1 and [C-11]carbon dioxide under atmospheric pressure in 15 +/- 2% uncorrected radiochemical yield (n = 3), based on [C-11]CO2. Judicious choice of solvents, catalysts, and additives, as well as precursor concentration and purity of [11C]CO2, enabled the preparation of this C-11-labeled carboxylic acid. Formulated [11C]bexarotene was isolated (>37 mCi) with >99% radiochemical purity in 32 mm. Preliminary positron emission tomography magnetic resonance imaging revealed rapid brain uptake in nonhuman primate in the first 75 s following intravenous administration of the radiotracer (specific activity >0.3 Ci/mu mol at time of injection), followed by slow clearance (Delta = 43%) over 60 min. Modest uptake (SUV = 0.8) was observed in whole brain and regions with high RXR expression.

  DOI：

  10.1021/ml500065q
• 作为产物：
  描述：

  2-(4-碘苯基)-(3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-基)-甲酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium hydrogen difluoride 、 potassium acetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.75h， 生成 potassium (4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)phenyl)trifluoroborate
  参考文献：
  名称：

  Synthesis of [¹¹C]Bexarotene by Cu-Mediated [¹¹C]Carbon Dioxide Fixation and Preliminary PET Imaging

  摘要：

  Bexarotene (Targretin) is a retinoid X receptor (RXR) agonist that has applications for treatment of T cell lymphoma and proposed mechanisms of action in Alzheimer's disease that have been the subject of recent controversy. Carbon-11 labeled bexarotene ([11C_ carbony1]4-[1-(3,5,5,8,8-pentamethylietralin-2-yOethenyllbenzoic acid) was synthesized using a Cu-mediated cross-coupling reaction employing an arylboronate precursor 1 and [C-11]carbon dioxide under atmospheric pressure in 15 +/- 2% uncorrected radiochemical yield (n = 3), based on [C-11]CO2. Judicious choice of solvents, catalysts, and additives, as well as precursor concentration and purity of [11C]CO2, enabled the preparation of this C-11-labeled carboxylic acid. Formulated [11C]bexarotene was isolated (>37 mCi) with >99% radiochemical purity in 32 mm. Preliminary positron emission tomography magnetic resonance imaging revealed rapid brain uptake in nonhuman primate in the first 75 s following intravenous administration of the radiotracer (specific activity >0.3 Ci/mu mol at time of injection), followed by slow clearance (Delta = 43%) over 60 min. Modest uptake (SUV = 0.8) was observed in whole brain and regions with high RXR expression.

  DOI：

  10.1021/ml500065q