tert-butyl 2-(N-benzoylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate | 1044741-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 2-(N-benzoylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate
• CAS: 1044741-54-9
• 化学式: C₂₈H₃₉IN₂O₆Si
• 分子量: 654.617
• InChiKey: MCKOTKJIQHNJOZ-JJKYIXSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  95.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(N-benzoylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 68.0h， 以56%的产率得到tert-butyl 2-(N'-benzoylhydrazino)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate
  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
• 作为产物：
  描述：

  tert-butyl 3-(tert-butyldimethylsilyloxy)-2-hydrazono-3-(2-iodo-4,5-dimethoxyphenyl)propionate 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到tert-butyl 2-(N-benzoylhydrazono)-3-(tert-butyldimethylsilyloxy)-3-(2-iodo-4,5-dimethoxyphenyl)propionate
  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