2-Phenyl-4-carbethoxyquinoline N-oxide | 61845-40-7

• 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-Phenyl-4-carbethoxyquinoline N-oxide
• 英文别名: 1-oxy-2-phenyl-quinoline-4-carboxylic acid ethyl ester；1-Oxy-2-phenyl-chinolin-4-carbonsaeure-aethylester；Ethyl 1-oxo-2-phenyl-1lambda~5~-quinoline-4-carboxylate；ethyl 1-oxido-2-phenylquinolin-1-ium-4-carboxylate
• CAS: 61845-40-7
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: SHKVKKJGYUAZIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 2-Phenyl-4-carbethoxyquinoline N-oxide 在 lead dioxide 作用下， 生成
  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