2,2-Diphenyl-1,2-dihydroquinolinenitroxide radical | 61845-44-1

• 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
• 英文名称: 2,2-Diphenyl-1,2-dihydroquinolinenitroxide radical
• 英文别名: 2,2-Diphenyl-1,2-dihydrochinolinyl-1-oxyl；1,2-Dihydro-2,2-diphenylquinoline-1-oxyl；1,2-dihydro-2,2-diphenylquinoline 1-oxyl；2,2-diphenyl-1,2-dihydroquinoline-N-oxyl
• CAS: 61845-44-1
• 化学式: C₂₁H₁₆NO
• 分子量: 298.364
• InChiKey: NVEVPMWUGDOMJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-Diphenyl-1,2-dihydroquinolinenitroxide radical 在 铁粉 、 溶剂黄146 作用下， 反应 0.08h， 以70%的产率得到2,2-Diphenyl-1,2-dihydrochinolin
  参考文献：
  名称：

  Oxidative dimerization of quinolinic nitroxides in the presence of trichloro- and trifluoro- acetic acid. Crystal structures of 6,6′-bis-(1-oxide-1,2,6,8a-tetrahydroquinoline)ylidene and of 2,3-diphenylquinoline

  摘要：

  Quinolinic nitroxides 1a-c react with trichloro- (TCA) and trifluoro- (TFA) acetic acid to give dimers 3a-c and quinolines 4a-c as the main products. Products 3a-c are explained as arising via the intermediate formation of the radical cation 5, which forms the final dimer through an oxidative dimerization promoted by the TCA or TFA. The formation of products 4a-c is explained by a Wagner-Meerwein type transposition of the phenyl group from C-2 to C-3. The disproportionation, which generally occurs in the presence of acid for nitroxides having the N-O function conjugated with a pi-system, has been excluded even though quinoneimine N-oxides 2a-c were isolated. The structure of compounds 3a and 4a were determined by crystal X-ray analysis.

  DOI：

  10.1016/s0040-4020(01)81875-5
• 作为产物：
  描述：

  2-methoxyquinoline 1-oxide 、 phenylmagnesium bromide 在 lead dioxide 作用下， 生成 2,2-Diphenyl-1,2-dihydroquinolinenitroxide radical 、 2-phenylquinoline 1-oxide
  参考文献：
  名称：

  Colonna, Martino; Greci, Lucedio; Poloni, Marino, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 293 - 297

  摘要：

  DOI：

文献信息

• Zur Reaktion von 2,2-Diphenyl-1,2-dihydrochinolin-Nitroxid-Radikalen mit dem NO-Donator SIN-1 (3-Morpholinosydnonimin)
  作者：Horst Weber、Andreas Grzesiok、Hans-Gert Korth、Reiner Sustmann

  DOI：10.1002/ardp.19943271207

  日期：——

  Die Nitroxid‐Radikale 1 eignen sich zum in situ‐Nachweis von Stickstoffmonoxid (NO˙), das unter aeroben Bedingungen aus dem Molsidomin‐Metaboliten SIN‐1 (3‐Morpholinosydnonimin) freigesetzt wird. Außer den stabilen Produkten 2, 3 und 4 entstehen bei dieser Reaktion auch die instabilen Aminoxyle 5, die sich zu den stabilen Folgeprodukten 3, 6 und 7 zersetzen. 7a entsteht auch bei der Reaktion von la

  氮氧自由基 1 适用于在有氧条件下从 molsidomine 代谢物 SIN-1（3-morpholinosydnonimine）释放的一氧化氮 (NO·) 的原位检测。除了稳定的产物 2、3 和 4，该反应还产生不稳定的氨氧基 5，其分解为稳定的副产物 3、6 和 7。图7a也由Ia与芬顿试剂反应形成。7b 可以通过六氰基铁酸盐 (III) 氧化独立于氮氧化合物 8 制备。化合物 2-5 的形成模式是在 1 对一氧化氮 (NO·) 和二氧化氮 (NO2·) 的相对反应性的背景下讨论的。
• Weber, Horst; Grzesiok, Andreas; Sustmann, Reiner, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 8, p. 1041 - 1050
  作者：Weber, Horst、Grzesiok, Andreas、Sustmann, Reiner、Korth, Hans-Gert

  DOI：——

  日期：——
• Cardellini, Liberato; Carloni, Patricia; Damiani, Elisabetta, journal of the chemical society-perkin transactions 2, 1994, # 4, p. 769 - 774
  作者：Cardellini, Liberato、Carloni, Patricia、Damiani, Elisabetta、Greci, Lucedio、Stipa, Pierluigi、et al.

  DOI：——

  日期：——
• Oxidative dimerization of quinolinic nitroxides in the presence of trichloro- and trifluoro- acetic acid. Crystal structures of 6,6′-bis-(1-oxide-1,2,6,8a-tetrahydroquinoline)ylidene and of 2,3-diphenylquinoline
  作者：Patricia Carloni、Elisabetta Damiani、Lucedio Greci、Pierluigi Stipa、Corrado Rizzoli、Paolo Sgarabotto、Franco Ugozzoli

  DOI：10.1016/s0040-4020(01)81875-5

  日期：1993.6

  Quinolinic nitroxides 1a-c react with trichloro- (TCA) and trifluoro- (TFA) acetic acid to give dimers 3a-c and quinolines 4a-c as the main products. Products 3a-c are explained as arising via the intermediate formation of the radical cation 5, which forms the final dimer through an oxidative dimerization promoted by the TCA or TFA. The formation of products 4a-c is explained by a Wagner-Meerwein type transposition of the phenyl group from C-2 to C-3. The disproportionation, which generally occurs in the presence of acid for nitroxides having the N-O function conjugated with a pi-system, has been excluded even though quinoneimine N-oxides 2a-c were isolated. The structure of compounds 3a and 4a were determined by crystal X-ray analysis.
• Colonna, Martino; Greci, Lucedio; Poloni, Marino, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 293 - 297
  作者：Colonna, Martino、Greci, Lucedio、Poloni, Marino

  DOI：——

  日期：——