7-methoxy-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 1389321-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-methoxy-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• 英文别名: 3-Cyclobutyl-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[D]azepine；3-cyclobutyl-7-methoxy-1,2,4,5-tetrahydro-3-benzazepine
• CAS: 1389321-47-4
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: NIWSQMXNRANDIA-UHFFFAOYSA-N

物化性质

• 沸点：
  354.3±42.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 在 氢溴酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 溶剂黄146 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.5h， 生成 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide
  参考文献：
  名称：

  A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor

  摘要：

  GSK189254 and its corresponding precursor GSK185071B were synthesized from 3-methoxyphenylacetic acid with 6-chloropyridine-3-carbolic acid or 6-chloronicotinamide in 8 and 7 steps with either 6% or 7% and either 14% or 16% yield, respectively. [C-11]GSK189254 was prepared from GSK185071B with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 50-60% radiochemical yield based on [C-11]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/mu mol specific activity at EOB. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.076
• 作为产物：
  描述：

  3-甲氧基苯基乙酰氯 在 盐酸 、 硼烷四氢呋喃络合物 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 三甲胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 8.5h， 生成 7-methoxy-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor

  摘要：

  GSK189254 and its corresponding precursor GSK185071B were synthesized from 3-methoxyphenylacetic acid with 6-chloropyridine-3-carbolic acid or 6-chloronicotinamide in 8 and 7 steps with either 6% or 7% and either 14% or 16% yield, respectively. [C-11]GSK189254 was prepared from GSK185071B with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 50-60% radiochemical yield based on [C-11]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/mu mol specific activity at EOB. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.076

文献信息

• Bioorg. Med. Chem. Lett. 2012, 22, 4713-4718
  作者：

  DOI：——

  日期：——
• A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor
  作者：Min Wang、Mingzhang Gao、Brandon L. Steele、Barbara E. Glick-Wilson、Clive Brown-Proctor、Anantha Shekhar、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2012.05.076

  日期：2012.7

  GSK189254 and its corresponding precursor GSK185071B were synthesized from 3-methoxyphenylacetic acid with 6-chloropyridine-3-carbolic acid or 6-chloronicotinamide in 8 and 7 steps with either 6% or 7% and either 14% or 16% yield, respectively. [C-11]GSK189254 was prepared from GSK185071B with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 50-60% radiochemical yield based on [C-11]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/mu mol specific activity at EOB. (C) 2012 Elsevier Ltd. All rights reserved.