2-甲氧基-6-(1-戊炔-1-基)吡啶 | 385825-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲氧基-6-(1-戊炔-1-基)吡啶
• 英文名称: 2-methoxy-6-(1-pentynyl)pyridine
• 英文别名: 2-Methoxy-6-pent-1-ynylpyridine
• CAS: 385825-97-8
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: ZTNCSWBLOFFKJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲氧基-6-(1-戊炔-1-基)吡啶 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 氢溴酸 、 氢气 、 溴 、 溶剂黄146 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 82.0h， 生成 cis-3-(3-hydroxycyclohexyl)-6-pentyl-1-propyl-2-pyridone
  参考文献：
  名称：

  A Pyridone Analogue of Traditional Cannabinoids. A New Class of Selective Ligands for the CB 2 Receptor

  摘要：

  A pyridone analogue (5) of the potent bicyclic cannabinoid CP 47,497 (6) has been synthesized as a model for one conformational isomer of anandamide and to test the hypothesis that an amide carbonyl may serve as a hydrogen bond acceptor in interactions with the CB1 cannabinoid receptor. Pyridone 5 was synthesized from 6-bromo-2-methoxypyridine (10) by palladium catalyzed coupling with 1-pentyne to provide 11. Catalytic hydrogenation of 11 and hydrolysis to pyridone 13 followed by N-alkylation gave 1-propyl-6-pentyl-2-pyridone (15). Bromination of 15 gave dibromide 18, which underwent Heck coupling with cyclohex-2-en-1-one to give enone 19, Catalytic hydrogenation of 19 gave ketone 20 which was reduced using NaBH4 to alcohol 5. Reduction of 20 with K-Selectride gave the axial epimer of 5 (21). Neither alcohol 5 nor 21 have significant affinity for the CB, receptor (K-i > 970 nM), but both have moderately high affinity for the CB2 receptor (K-i < 60 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00155-9
• 作为产物：
  描述：

  2-溴-6-甲氧基吡啶 、 1-戊炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以91%的产率得到2-甲氧基-6-(1-戊炔-1-基)吡啶
  参考文献：
  名称：

  A Pyridone Analogue of Traditional Cannabinoids. A New Class of Selective Ligands for the CB 2 Receptor

  摘要：

  A pyridone analogue (5) of the potent bicyclic cannabinoid CP 47,497 (6) has been synthesized as a model for one conformational isomer of anandamide and to test the hypothesis that an amide carbonyl may serve as a hydrogen bond acceptor in interactions with the CB1 cannabinoid receptor. Pyridone 5 was synthesized from 6-bromo-2-methoxypyridine (10) by palladium catalyzed coupling with 1-pentyne to provide 11. Catalytic hydrogenation of 11 and hydrolysis to pyridone 13 followed by N-alkylation gave 1-propyl-6-pentyl-2-pyridone (15). Bromination of 15 gave dibromide 18, which underwent Heck coupling with cyclohex-2-en-1-one to give enone 19, Catalytic hydrogenation of 19 gave ketone 20 which was reduced using NaBH4 to alcohol 5. Reduction of 20 with K-Selectride gave the axial epimer of 5 (21). Neither alcohol 5 nor 21 have significant affinity for the CB, receptor (K-i > 970 nM), but both have moderately high affinity for the CB2 receptor (K-i < 60 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00155-9