tert-butyl cinnoline-3-carboxylate | 1044741-66-3

• 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 cinnoline-3-carboxylate
• 英文别名: Tert-butyl cinnoline-3-carboxylate
• CAS: 1044741-66-3
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: QUCXGSYEYGEMIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C₁₅H₂₀BIN₂O₃ 在 copper(l) iodide 、 cesium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以13.3 mg的产率得到tert-butyl cinnoline-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

文献信息

• Novel Synthesis of Cinnolines and 1-Aminoindolines via Cu-Catalyzed Intramolecular N<i>-</i>Arylation of Hydrazines and Hydrazones Prepared from 3-Haloaryl-3-hydroxy-2-diazopropanoates
  作者：Kazuya Hasegawa、Naoki Kimura、Shigeru Arai、Atsushi Nishida

  DOI：10.1021/jo8010864

  日期：2008.8.1

  [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).