2-(2'-氟-5'-吡啶基)-7-氮杂双环(2.2.1)庚烷 | 176971-40-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 地棘蛙素类似物
• 中文名称: 2-(2'-氟-5'-吡啶基)-7-氮杂双环(2.2.1)庚烷
• 英文名称: [18F]norchlorofluoroepibatidine
• 英文别名: 2-(2-Fluoro-5-pyridyl)-7-azabicyclo(2.2.1)heptane；(1R,2R,4S)-2-(6-(18F)fluoranylpyridin-3-yl)-7-azabicyclo[2.2.1]heptane
• CAS: 176971-40-7；185110-47-8
• 化学式: C₁₁H₁₃FN₂
• 分子量: 191.238
• InChiKey: DCJIJGZSYBOUGL-UKOBOBMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-(2'-氟-5'-吡啶基)-7-氮杂双环(2.2.1)庚烷 在 sodium cyanoborohydride 作用下， 生成 [18F]N-methyl-norchlorofluoroepibatidine
  参考文献：
  名称：

  Ding, Y.-S.; Fowler, J.S.; Volkow, N.D., Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 546 - 547

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl (1R,2R,4S)-2-(6-(18F)fluoranylpyridin-3-yl)-7-azabicyclo[2.2.1]heptane-7-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2'-氟-5'-吡啶基)-7-氮杂双环(2.2.1)庚烷
  参考文献：
  名称：

  Dolci; Dolle; Valette, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S502-S503

  摘要：

  DOI：

文献信息

• Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: (+/−)-exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane
  作者：Andrew Horti、Hayden T. Ravert、Edythe D. London、Robert F. Dannals

  DOI：10.1002/(sici)1099-1344(199604)38:4<355::aid-jlcr842>3.0.co;2-3

  日期：1996.4

  The radiochemical synthesis of (+/-)-exo-2-(2-[F-18]fluoro-5-pyridyl)-7-azabicyclo[2.2.1] heptane ([F-18]1) was accomplished by Kryptofix(R) 222 assisted nucleophilic no-carrier-added [F-18]fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-azabicyclo[2.2.1] heptane (3a). The average radiochemical yield of the final product was 10% and the average specific activity was greater than >2000 mCi/mu mol, calculated at end-of-synthesis. The stable fluorine ligand ([F-19]1) was prepared by Kryptofix(R) 222 assisted nucleophilic fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-methoxycarbonyl-7-azabicyclo [2.2.1]heptane (3b) followed by acid deprotection.
• Synthesis of [18F]norchlorofluoroepibatidine and its N-methyl derivative: new PET ligands for mapping nicotinic acetylcholine receptors
  作者：Y.-S. Ding、F. Liang、J. S. Fowler、M. J. Kuhar、F. I. Carroll

  DOI：10.1002/(sici)1099-1344(199710)39:10<827::aid-jlcr29>3.0.co;2-7

  日期：1997.10

  Fluorine-18 labeled norchlorofluoroepibatidine (NFEP), a high-affinity nicotinic acetylcholine receptor ligand, was prepared by a one-pot, two-step synthesis: nucleophilic heteroaromatic substitution of a tert-Boc protected precursor (7-tert-butyloxycarbonyl-exo-2-(2'-N,N,N-trimethylammonium-5'-pyridinyl)-7-[2.2.1]heptane iodide) using no-carrier-added [F-18]fluoride followed by deprotection with trifluoroacetic acid. Subsequent reductive N-methylation with formaldehyde and sodium cyanoborohydride afforded fluorine-lb labeled N-methyl-norchlorofluoroepibatidine (N-methyl-NFEP). The unusually high radiochemical yield for the first step (70%) and the quantitative conversions in the deprotection and N-methylation steps afforded overall radiochemical yields of 55-65% (decay corrected based on starting [F-18]fluoride) for [F-18]NFEP (synthesis time 65 min) and 45-55% for [F-18]N-methyl-NFEP (synthesis time 75 min), with a specific activity of 2-9 Ci/mu mole (EOB).
• Dolci; Dolle; Valette, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S502-S503
  作者：Dolci、Dolle、Valette、Vaufrey、Bottlaender、Crouzel

  DOI：——

  日期：——
• Ding, Y.-S.; Fowler, J.S.; Volkow, N.D., Journal of Labelled Compounds and Radiopharmaceuticals, <hi>1997</hi>, vol. 40, p. 546 - 547
  作者：Ding, Y.-S.、Fowler, J.S.、Volkow, N.D.、Liang, F.、Carroll, F.I.、Kuhar, M.J.

  DOI：——

  日期：——