3-bromo-5-(2H-tetrazol-5-yl)-1,2-oxazole | 1241897-96-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-bromo-5-(2H-tetrazol-5-yl)-1,2-oxazole
• CAS: 1241897-96-0
• 化学式: C₄H₂BrN₅O
• 分子量: 215.997
• InChiKey: NDEMNTNFPWRMCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙酸叔丁酯 、 3-bromo-5-(2H-tetrazol-5-yl)-1,2-oxazole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到1,1-Dimethylethyl 5-(3-bromo-5-isoxazolyl)-2H-tetrazole-2-acetate
  参考文献：
  名称：

  Development of a Practical Synthesis of Stearoyl-CoA Desaturase (SCD1) Inhibitor MK-8245

  摘要：

  A practical kilogram scale chromatography-free synthesis of stearoyl-CoA desaturase 1 (SCD1) inhibitor MK-8245 is described. The key features of this sequence include an efficient addition elimination reaction of a piperidine fragment with a 3-bromoisoxaline followed by an iodine-mediated oxidation to the corresponding isoxazole. The development of a safe and scalable tetrazole formation protocol is also presented.

  DOI：

  10.1021/op200186d
• 作为产物：
  描述：

  3-Bromoisoxazole-5-carbonitrile 在 sodium azide 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到3-bromo-5-(2H-tetrazol-5-yl)-1,2-oxazole
  参考文献：
  名称：

  Development of a Practical Synthesis of Stearoyl-CoA Desaturase (SCD1) Inhibitor MK-8245

  摘要：

  A practical kilogram scale chromatography-free synthesis of stearoyl-CoA desaturase 1 (SCD1) inhibitor MK-8245 is described. The key features of this sequence include an efficient addition elimination reaction of a piperidine fragment with a 3-bromoisoxaline followed by an iodine-mediated oxidation to the corresponding isoxazole. The development of a safe and scalable tetrazole formation protocol is also presented.

  DOI：

  10.1021/op200186d

文献信息

• Development of a Practical Synthesis of Stearoyl-CoA Desaturase (SCD1) Inhibitor MK-8245
  作者：Mélina Girardin、Sarah J. Dolman、Sophie Lauzon、Stéphane G. Ouellet、Greg Hughes、Paul Fernandez、George Zhou、Paul D. O’Shea

  DOI：10.1021/op200186d

  日期：2011.9.16

  A practical kilogram scale chromatography-free synthesis of stearoyl-CoA desaturase 1 (SCD1) inhibitor MK-8245 is described. The key features of this sequence include an efficient addition elimination reaction of a piperidine fragment with a 3-bromoisoxaline followed by an iodine-mediated oxidation to the corresponding isoxazole. The development of a safe and scalable tetrazole formation protocol is also presented.