5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-dimethylaminobenzoate | 286368-53-4

• 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: 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-dimethylaminobenzoate
• 英文别名: [5-(2-Phenoxyphenyl)-1,3,4-oxadiazol-2-yl] 4-(dimethylamino)benzoate
• CAS: 286368-53-4
• 化学式: C₂₃H₁₉N₃O₄
• 分子量: 401.422
• InChiKey: ASTAFPPLTDZLNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-dimethylaminobenzoate 在 potassium fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-fluorobenzoate
  参考文献：
  名称：

  One-step, no-carrier-added, synthesis of a18F-labelled benzodiazepine receptor ligand

  摘要：

  5-(2-Phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-fluorobenzoate, a non-classical benzodiazepine receptor ligand, has shown anticonvulsant activity against pentylenetetrazole-induced convulsion. In order to perform biological studies, we decided to label the compound with positron-emitting fluorine-ls (t(1/2)=109.7 min). The latter compound was prepared in no-carrier-added form from [(18)F]fluoride and 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-N,N,N-trimethylanilinium triflate in one step. The best results were obtained using Kryptofix2.2.2/[(18)F]fluoride with dimethylsulfoxide as the solvent at 90 degrees C. Column chromatography afforded the desired compound in 15 min in an overall radiochemical yield of 70-75% corrected to the end of radionuclide production with a specific radioactivity of about 3000 Ci/mmol and a radiochemical purity of more than 95% and high chemical purity.

  DOI：

  10.1002/(sici)1099-1344(200005)43:6<545::aid-jlcr340>3.0.co;2-1
• 作为产物：
  描述：

  4-二甲氨基苯甲酸 、 3H-2-oxo-5-(2-phenoxyphenyl)-1,3,4-oxadiazole 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以70%的产率得到5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-dimethylaminobenzoate
  参考文献：
  名称：

  One-step, no-carrier-added, synthesis of a18F-labelled benzodiazepine receptor ligand

  摘要：

  5-(2-Phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-fluorobenzoate, a non-classical benzodiazepine receptor ligand, has shown anticonvulsant activity against pentylenetetrazole-induced convulsion. In order to perform biological studies, we decided to label the compound with positron-emitting fluorine-ls (t(1/2)=109.7 min). The latter compound was prepared in no-carrier-added form from [(18)F]fluoride and 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-N,N,N-trimethylanilinium triflate in one step. The best results were obtained using Kryptofix2.2.2/[(18)F]fluoride with dimethylsulfoxide as the solvent at 90 degrees C. Column chromatography afforded the desired compound in 15 min in an overall radiochemical yield of 70-75% corrected to the end of radionuclide production with a specific radioactivity of about 3000 Ci/mmol and a radiochemical purity of more than 95% and high chemical purity.

  DOI：

  10.1002/(sici)1099-1344(200005)43:6<545::aid-jlcr340>3.0.co;2-1

文献信息

• One-step, no-carrier-added, synthesis of a18F-labelled benzodiazepine receptor ligand
  作者：Amir Reza Jalilian、Sayyed Abbas Tabatabai、Abbas Shafiee、Hossein Afarideh、Reza Najafi、Maria Bineshmarvasti

  DOI：10.1002/(sici)1099-1344(200005)43:6<545::aid-jlcr340>3.0.co;2-1

  日期：2000.5

  5-(2-Phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-fluorobenzoate, a non-classical benzodiazepine receptor ligand, has shown anticonvulsant activity against pentylenetetrazole-induced convulsion. In order to perform biological studies, we decided to label the compound with positron-emitting fluorine-ls (t(1/2)=109.7 min). The latter compound was prepared in no-carrier-added form from [(18)F]fluoride and 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-N,N,N-trimethylanilinium triflate in one step. The best results were obtained using Kryptofix2.2.2/[(18)F]fluoride with dimethylsulfoxide as the solvent at 90 degrees C. Column chromatography afforded the desired compound in 15 min in an overall radiochemical yield of 70-75% corrected to the end of radionuclide production with a specific radioactivity of about 3000 Ci/mmol and a radiochemical purity of more than 95% and high chemical purity.