| 1334553-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• CAS: 1334553-76-2
• 化学式: C₃₂H₃₉N₂O
• 分子量: 467.674
• InChiKey: KXJAZNAJPJXIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  16.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以10%的产率得到2,10-Ditert-butyl-12,12,14,14-tetramethyl-7-oxidoquinolino[3,2-b]acridin-5-ium 5-oxide
  参考文献：
  名称：

  Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to Nitroxide Diradical and Spirocyclic Products

  摘要：

  Oxidation of diaryldiamine 2, a tetrahydrodiazapentacene derivative, provides diarylnitroxide diradical 1 accompanied by an intermediate nitroxide monoradical and a multitude of isolable diamagnetic products. DFT-computed tensors for EPR spectra and paramagnetic H-1 NMR isotropic shifts for nitroxide diradical 1 show good agreement with the experimental EPR spectra in rigid matrices and paramagnetic H-1 NMR spectra in solution, respectively. Examination of the diamagnetic products elucidates their formation via distinct pathways involving C-O bond-forming reactions, including Baeyer-Villiger-type oxidations. An unusual diiminoketone structure and two spirocyclic structures of the predominant diamagnetic products are confirmed by either X-ray crystallography or correlations between DFT-computed and experimental spectroscopic data such as H-1, C-13, and N-15 NMR chemical shifts and electronic absorption spectra.

  DOI：

  10.1021/jo2017923
• 作为产物：
  描述：

  2,10-Di-tert-butyl-12,12,14,14-tetramethyl-5,7,12,14-tetrahydro-5,7-diaza-pentacene 在 sodium tungstate 、 双氧水 、 十二烷基三甲基氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 以30%的产率得到
  参考文献：
  名称：

  Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to Nitroxide Diradical and Spirocyclic Products

  摘要：

  Oxidation of diaryldiamine 2, a tetrahydrodiazapentacene derivative, provides diarylnitroxide diradical 1 accompanied by an intermediate nitroxide monoradical and a multitude of isolable diamagnetic products. DFT-computed tensors for EPR spectra and paramagnetic H-1 NMR isotropic shifts for nitroxide diradical 1 show good agreement with the experimental EPR spectra in rigid matrices and paramagnetic H-1 NMR spectra in solution, respectively. Examination of the diamagnetic products elucidates their formation via distinct pathways involving C-O bond-forming reactions, including Baeyer-Villiger-type oxidations. An unusual diiminoketone structure and two spirocyclic structures of the predominant diamagnetic products are confirmed by either X-ray crystallography or correlations between DFT-computed and experimental spectroscopic data such as H-1, C-13, and N-15 NMR chemical shifts and electronic absorption spectra.

  DOI：

  10.1021/jo2017923

文献信息

• Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to Nitroxide Diradical and Spirocyclic Products
  作者：Andrzej Rajca、Kouichi Shiraishi、Przemysław J. Boratyński、Maren Pink、Makoto Miyasaka、Suchada Rajca

  DOI：10.1021/jo2017923

  日期：2011.10.21

  Oxidation of diaryldiamine 2, a tetrahydrodiazapentacene derivative, provides diarylnitroxide diradical 1 accompanied by an intermediate nitroxide monoradical and a multitude of isolable diamagnetic products. DFT-computed tensors for EPR spectra and paramagnetic H-1 NMR isotropic shifts for nitroxide diradical 1 show good agreement with the experimental EPR spectra in rigid matrices and paramagnetic H-1 NMR spectra in solution, respectively. Examination of the diamagnetic products elucidates their formation via distinct pathways involving C-O bond-forming reactions, including Baeyer-Villiger-type oxidations. An unusual diiminoketone structure and two spirocyclic structures of the predominant diamagnetic products are confirmed by either X-ray crystallography or correlations between DFT-computed and experimental spectroscopic data such as H-1, C-13, and N-15 NMR chemical shifts and electronic absorption spectra.