tert-butyl 1-acetyl-4-(tert-butyldimethylsilyloxy)-7-chloro-1,4-dihydrocinnoline-3-carboxylate | 1044741-76-5

• 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: tert-butyl 1-acetyl-4-(tert-butyldimethylsilyloxy)-7-chloro-1,4-dihydrocinnoline-3-carboxylate
• 英文别名: tert-butyl 1-acetyl-4-[tert-butyl(dimethyl)silyl]oxy-7-chloro-4H-cinnoline-3-carboxylate
• CAS: 1044741-76-5
• 化学式: C₂₁H₃₁ClN₂O₄Si
• 分子量: 439.027
• InChiKey: GPKKZYCIOQCGRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(N-acetylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(4-chloro-2-iodophenyl)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100%的产率得到tert-butyl 1-acetyl-4-(tert-butyldimethylsilyloxy)-7-chloro-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

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).