methyl 6-methoxy-4-(trifluoromethyl)pyridazine-3-carboxylate | 1443778-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-methoxy-4-(trifluoromethyl)pyridazine-3-carboxylate
• CAS: 1443778-64-0
• 化学式: C₈H₇F₃N₂O₃
• 分子量: 236.15
• InChiKey: FGUQIEOKNFTHKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate 、 甲氧羰基亚甲基三苯基正膦 以 乙醚 为溶剂， 以11%的产率得到methyl 6-methoxy-4-(trifluoromethyl)pyridazine-3-carboxylate
  参考文献：
  名称：

  Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study

  摘要：

  Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16-37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37-69%). The configuration of the resulting F-and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.

  DOI：

  10.1055/s-0032-1318309