(-)-(1R,5S)-N-acetyl-9-amino-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one | 267401-47-8

• 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-amino-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
• 英文别名: (1R,9S)-11-acetyl-5-amino-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CAS: 267401-47-8
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: SHXZVQAUXLWPOL-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1R,5S)-N-acetyl-9-amino-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以71%的产率得到(-)-(1R,5S)-N-acetyl-1,2,3,4,5,6-hexahydro-1,5-methano-8-oxo-pyrido[1,2-a][1,5]diazocine-9-diazonium fluoroborate
  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：

  3-Nitrocytisine 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (-)-(1R,5S)-N-acetyl-9-amino-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

文献信息

• Synthesis of Analogues of (−)-Cytisine for in Vivo Studies of Nicotinic Receptors Using Positron Emission Tomography
  作者：Eddie Marrière、Jacques Rouden、Vincent Tadino、Marie-Claire Lasne

  DOI：10.1021/ol005685m

  日期：2000.4.1

  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.