(-)-(1R,5S)-N-acetyl-9-nitro-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one | 267401-45-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: (-)-(1R,5S)-N-acetyl-9-nitro-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
• CAS: 267401-45-6
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: IPTADXUTBUFBMZ-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  85.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-(1R,5S)-N-acetyl-9-nitro-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one 在 硝酸铵 、 三氟乙酸酐 作用下， 以 氯仿 为溶剂， 以70%的产率得到(-)-(1R,5S)-N-acetyl-9,11-dinitro-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
  参考文献：
  名称：

  Synthesis of Analogues of (−)-Cytisine for in Vivo Studies of Nicotinic Receptors Using Positron Emission Tomography

  摘要：

  9-Substituted analogues of (-)-cytisine were synthesized in high yields via palladium-mediated couplings of either 9- (-)-bromocytisine and organostannanes or 9-(-) trimethylstannylcytisine and fluorobromobenzene. The protection of the amine with a nitroso group and the use of PdCl2(PPh3)(2) to carry out the Stille reaction allowed the rapid synthesis of 9-(4'-[F-18]fluorophenyl)cytisine (F-18: t(1/2) = 109.7 min), a new promising radioligand (radiochemical yield: 10% from [F-18]KF, 150 min, four steps) for positron emission tomography studies of alpha(4)beta(2) nicotinic receptors.

  DOI：

  10.1021/ol005685m
• 作为产物：
  描述：

  乙酸酐 、 3-Nitrocytisine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以100%的产率得到(-)-(1R,5S)-N-acetyl-9-nitro-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
  参考文献：
  名称：

  Synthesis of Analogues of (−)-Cytisine for in Vivo Studies of Nicotinic Receptors Using Positron Emission Tomography

  摘要：

  9-Substituted analogues of (-)-cytisine were synthesized in high yields via palladium-mediated couplings of either 9- (-)-bromocytisine and organostannanes or 9-(-) trimethylstannylcytisine and fluorobromobenzene. The protection of the amine with a nitroso group and the use of PdCl2(PPh3)(2) to carry out the Stille reaction allowed the rapid synthesis of 9-(4'-[F-18]fluorophenyl)cytisine (F-18: t(1/2) = 109.7 min), a new promising radioligand (radiochemical yield: 10% from [F-18]KF, 150 min, four steps) for positron emission tomography studies of alpha(4)beta(2) nicotinic receptors.

  DOI：

  10.1021/ol005685m