2-甲基-4-(5-硝基吡啶-2-基)丁-3-炔-2-醇 | 379670-38-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-甲基-4-(5-硝基吡啶-2-基)丁-3-炔-2-醇
• 英文名称: 2-methyl-4-(5-nitropyridin-2-yl)but-3-yn-2-ol
• CAS: 379670-38-9
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: HURDUPBUACUCJN-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: ethanol (64-17-5))
• 沸点：
  361.5±37.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-4-(5-硝基吡啶-2-基)丁-3-炔-2-醇 在 硫酸 、 mercury(II) diacetate 、 水 、 potassium hydroxide 作用下， 以 丙酮 、 苯 为溶剂， 反应 5.0h， 生成 1-(5-硝基吡啶-2-基)乙酮
  参考文献：
  名称：

  Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

  摘要：

  Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.

  DOI：

  10.1134/s1070428010120109
• 作为产物：
  描述：

  2-羟基-5-硝基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四磷十氧化物 、 四丁基溴化铵 、 potassium acetate 作用下， 以 乙腈 、 苯 为溶剂， 反应 1.0h， 生成 2-甲基-4-(5-硝基吡啶-2-基)丁-3-炔-2-醇
  参考文献：
  名称：

  Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

  摘要：

  Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.

  DOI：

  10.1134/s1070428010120109

文献信息

• [EN] FUSED-RING COMPOUNDS, PHARMACEUTICAL COMPOSITION AND USES THEREOF<br/>[FR] COMPOSÉS À CYCLES FUSIONNÉS, COMPOSITION PHARMACEUTIQUE ET UTILISATIONS ASSOCIÉES
  申请人：SHANGHAI DE NOVO PHARMATECH CO LTD

  公开号：WO2016131381A1

  公开（公告）日：2016-08-25

  This disclosure is related to a fused-ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the fused ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in modulating activity of indoleamine 2, 3-dioxygenase (IDO) and/or tryptophan 2, 3-dioxygenase (TDO); this disclosure further provides methods of treating IDO and/or TDO-associated diseases, including cancer, viral infection and autoimmune diseases.