N-(2-aminoethyl)-4-chloro[carbonyl-11C]benzamide

• 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: N-(2-aminoethyl)-4-chloro[carbonyl-11C]benzamide
• 英文别名: N-(2-aminoethyl)-4-chlorobenzamide
• 化学式: C₉H₁₁ClN₂O
• 分子量: 197.641
• InChiKey: AIHKMGLJGLKLSI-RVRFMXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯碘苯 、 乙二胺 、 单氧化(~11~C)碳 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 130.0 ℃ 、35.0 MPa 条件下， 反应 0.08h， 生成 N-(2-aminoethyl)-4-chloro[carbonyl-11C]benzamide
  参考文献：
  名称：

  Biologically Active ¹¹C-Labeled Amides Using Palladium-Mediated Reactions with Aryl Halides and [¹¹C]Carbon Monoxide

  摘要：

  Using [C-11]carbon monoxide in palladium-mediated synthesis, six amides were labeled with C-11. Phenyl and benzyl halides with halides as additional substituents were carbonylated and reacted with primary and secondary amines. Four of the selected amides were receptor ligands, one was a precursor to a receptor ligand, and one was a model compound. The C-11-labeled amides were obtained with good to almost quantitative radiochemical yields with specific activities up to 1000 GBq/mu mol. The radiochemical purity of the final products exceeded 98%. In one case, the corresponding C-13- substituted compound was produced to verify the position of the label. In a typical experiment starting with 5.0 GBq of [C-11]carbon monoxide, 2.2 GBq of LC-purified N-(2-aminoethyl)-4-chloro-[carbonyl-C-11]benzamide was obtained within 15 min from the start of the carbonylation reaction (74% decay-corrected radiochemical yield). The presented approach gives significant new possibilities for C-11-labeling and is seen to be valuable also for synthesis of C-13- and C-14-substituted compounds.

  DOI：

  10.1021/jo990616a

文献信息

• Biologically Active ¹¹C-Labeled Amides Using Palladium-Mediated Reactions with Aryl Halides and [¹¹C]Carbon Monoxide
  作者：Tor Kihlberg、Bengt Långström

  DOI：10.1021/jo990616a

  日期：1999.12.1

  Using [C-11]carbon monoxide in palladium-mediated synthesis, six amides were labeled with C-11. Phenyl and benzyl halides with halides as additional substituents were carbonylated and reacted with primary and secondary amines. Four of the selected amides were receptor ligands, one was a precursor to a receptor ligand, and one was a model compound. The C-11-labeled amides were obtained with good to almost quantitative radiochemical yields with specific activities up to 1000 GBq/mu mol. The radiochemical purity of the final products exceeded 98%. In one case, the corresponding C-13- substituted compound was produced to verify the position of the label. In a typical experiment starting with 5.0 GBq of [C-11]carbon monoxide, 2.2 GBq of LC-purified N-(2-aminoethyl)-4-chloro-[carbonyl-C-11]benzamide was obtained within 15 min from the start of the carbonylation reaction (74% decay-corrected radiochemical yield). The presented approach gives significant new possibilities for C-11-labeling and is seen to be valuable also for synthesis of C-13- and C-14-substituted compounds.