3,5-di(trifluoromethyl)[carbonyl-11C]benzoyl chloride | 848440-89-1

• 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: 3,5-di(trifluoromethyl)[carbonyl-11C]benzoyl chloride
• 英文别名: [11C]3,5-bis(trifluoro)benzoyl chloride；3,5-bis(trifluoromethyl)benzoyl chloride
• CAS: 848440-89-1
• 化学式: C₉H₃ClF₆O
• 分子量: 275.555
• InChiKey: WAKMMQSMEDJRRI-JZRMKITLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N1-(2,6-dimethylphenyl)-2-{4-[(2R,4S)-2-benzylhexahydro-4-pyridinyl]piperazino}acetamide 、 3,5-di(trifluoromethyl)[carbonyl-11C]benzoyl chloride 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.02h， 生成 N1-(2,6-dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl)[carbonyl-11C]benzoyl]hexahydro-4-pyridinyl}piperazino)acetamide
  参考文献：
  名称：

  Synthesis and biodistribution of [11C]R116301, a promising PET ligand for central NK1 receptors

  摘要：

  Nl-(2,6-Dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl)[carbonyl-C-11]benzoyl]hexahydro-4-pyridinyl}-piperazino)acetamide ([C-11]R116301) was prepared and evaluated as a potential positron emission tomography (PET) ligand for investigation of central neurokinin(l) (NK1) receptors. 1-Bromo-3,5-di(trifluoromethyl) benzene was converted in three steps into 3,5-di(trifluoromethyl)[carbonyl-C-11]benzoyl chloride, which was reacted with N1-(2,6-dimethylphenyl)-2-{4-[(2R,4S)-2-benzylhexa-hydro-4-pyridinyl]piperazino}acetamide providing [C-11]R116301 in 45-57% decay-corrected radiochemical yield. The total synthesis time, from end of bombardment (EOB) to the formulated product, was 35 min. Specific activity (SA) was 82-172 GBq/mumol (n = 10) at the end of synthesis. N1-([4-H-3]-2,6-Dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl benzoyl]hexahydro-4-pyridinyl piperazino)acetamide ([H-3]R116301) was also synthesized (SA: 467 GBq/mmol). The B-max for [H-3]R116301 measured in vitro on Chinese hamster ovary cell membranes stably transfected with the human NK1 receptor was 19.10 +/- 1.02 pmol/mg protein with an apparent dissociation constant of 0.08 +/- 0.01 nM. Ex vivo, in vivo and in vitro autoradiography studies with [H-3]R 116301 in gerbils demonstrated a preferential accumulation of the radioactivity in the striatum, olfactory tubercule, olfactory bulb and locus coeruleus. In vivo, the biodistribution of [C-11]R116301 in gerbils revealed that the highest initial uptake is in the lung, followed by the liver and kidney. In the brain, maximum accumulation was found in the olfactory tubercules (1.10 +/- 0.08 injected dose (ID)/g 20 min post injection (p.i.)) and the nucleus accumbens (1.00 +/- 0.12 ID/g 10 min p.i.). Tissue/cerebellum concentration ratios for striatum and nucleus accumbens increased with time due to rapid uptake followed by a slow wash out (1.29 and 1.64, respectively, 30 min p.i.). A tissue to cerebellum ratio of 1.33 and 1.62 was also observed for olfactory bulb and olfactory tubercules, respectively (20 min p.i.). In summary, [C-11]R116301 appears to be a promising radioligand suitable for the visualization of NK1 receptors in vivo using PET. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.019
• 作为产物：
  描述：

  3,5-di(trifluoromethyl)[carboxy-11C]benzoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 3,5-di(trifluoromethyl)[carbonyl-11C]benzoyl chloride
  参考文献：
  名称：

  N,N?,N?,N?-tetraalkylcyclam derivatives: synthesis,99mTc-labelling and biological properties

  摘要：

  我们合成了一系列N,N′,N″,N‴-四烷基环四甲撑二胺衍生物，其中烷基包括乙基、丙基、丁基、甲氧基乙基和乙氧基乙基。我们尝试用99mTc标记这些化合物。含有甲基、乙基和丙基的环胺类化合物能够被标记。标记后的N,N′,N″,N‴-四烷基环四甲撑二胺衍生物带有+1电荷，它们在小鼠体内通过肾脏迅速排泄。随着脂溶性增加，肝脏摄取略有上升，但心肌摄取量低，与带+1电荷的心肌成像剂不同。版权所有 © 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.448