tert-butyl 6,7-dimethoxycinnoline-3-carboxylate | 1044741-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: tert-butyl 6,7-dimethoxycinnoline-3-carboxylate
• CAS: 1044741-74-3
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: HQABDKVTFLMHOA-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C(Solvent: Hexane; Ethyl acetate)
• 沸点：
  419.5±55.0 °C(predicted)
• 密度：
  1.182±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.54
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(N-acetylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate 在 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以68%的产率得到tert-butyl 1-acetyl-4-(tert-butyldimethylsilyloxy)-6,7-dimethoxy-1,4-dihydrocinnoline-3-carboxylate
  参考文献：
  名称：

  Novel Synthesis of Cinnolines and 1-Aminoindolines via Cu-Catalyzed Intramolecular N-Arylation of Hydrazines and Hydrazones Prepared from 3-Haloaryl-3-hydroxy-2-diazopropanoates

  摘要：

  [GRAPHICS]A new and facile access to cinnolines, dihydrocinnolines, and 1-aminoindolines was established by use of diazo functionalities. The hydrazines and hydrazones as cyclization precursors derived from 3-haloaryl-3-hydroxy-2-diazopropanoates, which are prepared by one-pot procedure utilizing phase-transfer catalysis, are successfully converted to the corresponding nitrogen heterocycle by Cu-catalyzed N-arylation. Furthermore, analysis of UV spectra proved that 4-oxo-3-carboxylates predominantly exist not as 4-hydroxycinnoline (enol form) but as cinnolone (keto form).

  DOI：

  10.1021/jo8010864