2-naphthalen-2-yl-4,5-dihydro-1H-[2-11C]-imidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthalen-2-yl-4,5-dihydro-1H-[2-11C]-imidazole
• 英文别名: [11C]benazoline；2-naphthalen-2-yl-(211C)4,5-dihydro-1H-imidazole
• 化学式: C₁₃H₁₂N₂
• 分子量: 195.241
• InChiKey: BGWRJAXPPYHIRG-HSGWXFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-diaminoethane dihydrochloride 、 2-[carboxyl-11C]naphthoic acid 在 乙二胺 作用下， 反应 0.13h， 生成 2-naphthalen-2-yl-4,5-dihydro-1H-[2-11C]-imidazole
  参考文献：
  名称：

  Radiosynthesis of a 2-substituted 4,5-dihydro-1H-[2-¹¹C] imidazole: the I₂imidazoline receptor ligand [¹¹C] benazoline

  摘要：

  贝那唑啉（2-萘-2-基-4,5-二氢-1H-咪唑）是一种选择性高亲和力的咪唑啉I2受体配体。该化合物在其2-咪唑啉环的第二个碳原子上标记了碳-11（半衰期=20.4分钟）。由回旋加速器产生的[11C]二氧化碳与2-萘基溴化镁反应，以60%的放射化学产率生成2-[羧基-11C]萘酸。后者在300°C下与乙二胺及其二盐酸盐混合加热，相对于[11C]二氧化碳，以16%的总产率得到[11C]贝那唑啉，且比活性为54 GBq/μmol，考虑到辐照结束时的衰变。该过程从回旋加速器辐照结束开始大约需要45分钟。这种方法应可扩展到其他咪唑啉类化合物。版权所有 © 2003 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.746

文献信息

• Roeda, D.; Hinnen, F.; Dolle, F., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S147 - S147
  作者：Roeda, D.、Hinnen, F.、Dolle, F.

  DOI：——

  日期：——
• Novel synthesis of 11C‐labeled imidazolines via Pd(0)‐mediated 11C‐carbomethoxylation using [11C]CO and arylborons
  作者：Hideki Ishii、Katsuyuki Minegishi、Kotaro Nagatsu、Nobuki Nengaki、Ming‐Rong Zhang

  DOI：10.1002/jlcr.4072

  日期：2024.5.30

  A labeling technique was developed for the imidazoline I2 receptor ligand 2‐(3‐fluoro‐tolyl)‐4, 5‐dihydro‐1H‐imidazole (FTIMD) using Pd(0)‐mediated 11C‐carbomethoxylation with [11C]CO, followed by imidazoline ring formation with ethylenediamine‐trimethylaluminium (EDA‐AlMe3). To achieve this, [11C]CO was passed through a methanol (MeOH) solution containing 3‐fluoro‐4‐methylphenylboronic acid (1), palladium (II) acetate (Pd [OAc]2), triphenylphosphine (PPh3), and p‐benzoquinone (PBQ). The mixture was then heated at 65°C for 5 min. EDA was introduced into the reaction mixture, and MeOH was completely evaporated at temperatures exceeding 100°C. The dried reaction mixture was combined with an EDA‐AlMe (1:1) toluene solution and heated at 145°C for 10 min. Portions of the reaction mixture were analyzed through high‐performance liquid chromatography, resulting in [11C]FTIMD with 26% (n = 2) decay‐corrected radiochemical yield (RCY). This method could be utilized for various arylborons to produce [2‐11C]imidazolines 4a–h with RCYs ranging from low to moderate. Notably, [2‐11C]benazoline was obtained with a moderate RCY of 65%. The proposed technique serves as an alternative to the Grignard method, which uses [11C]CO to generate a [2‐11C]‐labeled imidazoline ring.