[11C]2-methylbenzonitrile

• 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: [11C]2-methylbenzonitrile
• 英文别名: 2-methylbenzonitrile
• 化学式: C₈H₇N
• 分子量: 116.139
• InChiKey: NWPNXBQSRGKSJB-KWCOIAHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (η⁶-1-fluoro-2-methylbenzene)tricarbonylchromium(0) 以34%的产率得到
  参考文献：
  名称：

  ADAM, M. J.;BALATONI, J. A.;HALL, L. D., J. LABELL. COMPOUNDS AND RADIOPHARM., 26,(1989) C. 72

  摘要：

  DOI：

文献信息

• Palladium(<scp>ii</scp>)-mediated rapid ¹¹C-cyanation of (hetero)arylborons
  作者：Zhouen Zhang、Takashi Niwa、Yasuyoshi Watanabe、Takamitsu Hosoya

  DOI：10.1039/c8ob02049c

  日期：——

  A highly efficient method applicable to the synthesis of a wide range of [¹¹C]cyanoarenes, including PET tracers for aromatase imaging, has been developed by a palladium(ii)-mediated rapid ¹¹C-cyanation of (hetero)arylborons with [¹¹C]cyanides.

  一种高效的方法被开发出来，适用于合成广泛的[¹¹C]氰基芳烃，包括PET显像的芳香化酶探针，该方法是通过钯（ii）介导的快速¹¹C-氰基化反应，将(hetero)arylborons和[¹¹C]氰化物反应。
• Evaluation and improvement of CuI‐mediated ¹¹ C‐cyanation
  作者：Hideki Ishii、Tomoteru Yamasaki、Toshimitsu Okamura、Yiding Zhang、Yusuke Kurihara、Masanao Ogawa、Nobuki Nengaki、Ming‐Rong Zhang

  DOI：10.1002/jlcr.4016

  日期：2023.3

  CuI-mediated 11C-cyanation was evaluated by synthesizing [11C]perampanel ([11C]5) as a model compound and compared with previous reports. To a DMF solution with 5′-(2-bromophenyl)-1′-phenyl-[2,3′-bipyridin]-6′(1′H)-one (4) and CuI, [11C]NH4CN in a stream of ammonia/nitrogen (5:95, v/v) gas was bubbled. Subsequently, the reaction mixture was heated at 180°C for 5 min. After HPLC purification, [11C]5 was obtained in 7.2 ± 1.0% (n = 4) non-decay corrected radiochemical yield with >99% radiochemical purity and a molar activity of 98 ± 28 GBq/μmol. In vivo evaluations of [11C]5 were performed using small animals. PET scans to check the kinetics of [11C]5 in the whole body of mice suggested that [11C]5 spreads rapidly into the brain, heart, and lungs and then accumulates in the small intestine. To evaluate the performance of CuI-mediated 11C-cyanation reaction, bromobenzene (6a) was selected as the model compound; however, it failed. Therefore, optimization of the reaction conditions has been performed, and consequently, the addition of K2CO3 and prolonging the reaction time improved the radiochemical yield about double. With this improved method, CuI-mediated 11C-cyanation of various (hetero)aromatic bromides was performed to exhibit the tolerance of most functional groups and to provide 11C-cyanated products in good to moderate radiochemical yields.