(S)-12-methyl-12,13-dihydro-[1,2,3]triazolo[1',5':5,6][1,2,5]triazepino[1,2-a]indazol-10(4H)-one | 1392125-46-0

• 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)-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)-9-methyl-1,5,6,7,10-pentazatetracyclo[8.7.0.03,7.012,17]heptadeca-3,5,12,14,16-pentaen-11-one
• CAS: 1392125-46-0
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: XNVMFMZHMVLHKW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-3-methyl-2,3-dihydrooxazolo[3,2-b]indazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 (S)-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

文献信息

• A One-Pot–Three-Step Route to Triazolotriazepinoindazolones from Oxazolino-2<i>H</i>-indazoles
  作者：Wayne E. Conrad、Kevin X. Rodriguez、Huy H. Nguyen、James C. Fettinger、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/ol3015804

  日期：2012.8.3

  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.