(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 | 1392125-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: (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
• 英文别名: (9S)-15-bromo-4-ethyl-9-methyl-1,5,6,7,10-pentazatetracyclo[8.7.0.03,7.012,17]heptadeca-3,5,12(17),13,15-pentaen-11-one
• CAS: 1392125-66-4
• 化学式: C₁₅H₁₆BrN₅O
• 分子量: 362.229
• InChiKey: QWMJPWCNTAHREJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 (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 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以73%的产率得到(S)-3-ethyl-12-methyl-7-(pyrrolidin-1-yl)-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：

  (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