(S)-7-bromo-3-methyl-2,3-dihydrooxazolo[3,2-b]indazole | 1392125-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: (S)-7-bromo-3-methyl-2,3-dihydrooxazolo[3,2-b]indazole
• 英文别名: (3S)-7-bromo-3-methyl-2,3-dihydro-[1,3]oxazolo[3,2-b]indazole
• CAS: 1392125-65-3
• 化学式: C₁₀H₉BrN₂O
• 分子量: 253.098
• InChiKey: AMOVDPVZUNIJDH-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-7-bromo-3-methyl-2,3-dihydrooxazolo[3,2-b]indazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-7-bromo-3-ethyl-12-methyl-12,13-dihydro-[1,2,3]triazolo[1',5':5,6][1,2,5]triazepino[1,2-a]indazol-10(4H)-one
  参考文献：
  名称：

  A One-Pot–Three-Step Route to Triazolotriazepinoindazolones from Oxazolino-2H-indazoles

  摘要：

  A one-pot-three-step method has been developed for the conversion of oxazolino-2H-indazoles into triazolotriazepinoindazolones with three points of diversity. Step one of this process involves a propargyl bromide-initiated ring opening of the oxazolino-2H-indazole (available by the Davis-Beirut reaction) to give an N-1-(propargyl)-N-2-(2-bromoethyl)-disubstituted indazoione, which then undergoes -CH2Br -> -CH2N3 displacement (step two) followed by an uncatalyzed intramolecular azide-alkyne 1,3-dipolar cycloaddition (step three) to form the target heterocycle. Employing 7-bromooxazolino-2H-Indazole allows for further diversification through, for example, palladium-catalyzed coupling chemistry, as reported here.

  DOI：

  10.1021/ol3015804
• 作为产物：
  描述：

  4-甲基-3-硝基苯胺 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氢溴酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 异丙醇 为溶剂， 反应 57.0h， 生成 (S)-7-bromo-3-methyl-2,3-dihydrooxazolo[3,2-b]indazole
  参考文献：
  名称：

  A One-Pot–Three-Step Route to Triazolotriazepinoindazolones from Oxazolino-2H-indazoles

  摘要：

  A one-pot-three-step method has been developed for the conversion of oxazolino-2H-indazoles into triazolotriazepinoindazolones with three points of diversity. Step one of this process involves a propargyl bromide-initiated ring opening of the oxazolino-2H-indazole (available by the Davis-Beirut reaction) to give an N-1-(propargyl)-N-2-(2-bromoethyl)-disubstituted indazoione, which then undergoes -CH2Br -> -CH2N3 displacement (step two) followed by an uncatalyzed intramolecular azide-alkyne 1,3-dipolar cycloaddition (step three) to form the target heterocycle. Employing 7-bromooxazolino-2H-Indazole allows for further diversification through, for example, palladium-catalyzed coupling chemistry, as reported here.

  DOI：

  10.1021/ol3015804