5-Methyl-5,6-dihydro-6-phenanthridincarbonitril | 72501-44-1

• 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: 5-Methyl-5,6-dihydro-6-phenanthridincarbonitril
• 英文别名: 9-cyano-N-methyl-9,10-dihydrophenanthridine；5,6-dihydro-6-cyano-5-methylphenanthridine；5-methyl-5,6-dihydro-phenanthridine-6-carbonitrile；5-Methyl-5,6-dihydro-phenanthridin-6-carbonitril；N-Methyl-6-cyano-5,6-dihydrophenanthridin；5-methyl-6H-phenanthridine-6-carbonitrile
• CAS: 72501-44-1
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: HTFAPQYICMNWOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Methyl-5,6-dihydro-6-phenanthridincarbonitril 在 1,4-Di-tert-butyl-1,4-bis(3,5-di-tert-butylphenyl)-2-tetrazen 作用下， 以 苯 为溶剂， 生成 6-Cyan-5-methyl-5,6-dihydro-6-phenanthridinyl-Radikal
  参考文献：
  名称：

  Aurich, Hans Guenter; Deuschle, Eberhardt, Liebigs Annalen der Chemie, 1981, # 4, p. 719 - 733

  摘要：

  DOI：
• 作为产物：
  描述：

  N-methyl phenanthridinium iodide 以67%的产率得到
  参考文献：
  名称：

  Dostal Ji, Potaek Milan, Nechvatal Miloslav, Collect. Czechosl. Chem. Commun., 58 (1993) N 2, S 395-403

  摘要：

  DOI：

文献信息

• Reactions of 5-Methylphenanthridinium Iodide with Nucleophiles and Reaction Products Conversion
  作者：Jiří Dostál、Milan Potáček、Miloslav Nechvátal

  DOI：10.1135/cccc19930395

  日期：——

  Reactions of 5-methylphenanthridinium iodide (I) with oxygen, nitrogen, and carbon nucleophiles, respectively, were studied. 5-Methylphenanthridinium iodide (I) yielded in the basic aqueous medium 5-methyl-6-phenanthridone (II) and 5,6-dihydro-5-methylphenanthridine (III). By NMR spectroscopy in the D₂O-CD₃CN solution 5,6-dihydro-6-deuteroxy-5-methylphenanthridine (IVb) (pseudobase) was observed as an immediate unstable product. 5-Methylphenanthridinium iodide (I) gave the corresponding adducts with methoxide and ethoxide anions, morpholine, piperidine, pyrrolidine, cyanide anion and acetone. Their structure was determined by IR, ¹H and ¹³C NMR spectroscopy. Reactions of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) were followed by NMR spectroscopy. Morpholino adduct VII gave in the CD₃CN-D₂O solution pseudobase (IVb) and its products of disproportionation: oxophenanthridine II and dihydrophenanthridine III. Treatment of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) with H₂O/D₂O in (CH₃)₂CO/(CD₃)₂CO led to CH₃COCH₂-/CD₃COCD₂- adduct XIa/XIb formation, respectively.

  研究了5-甲基菲啶铵碘（I）分别与氧、氮和碳亲核试剂发生的反应。在碱性水介质中，5-甲基菲啶铵碘（I）生成5-甲基-6-菲啶酮（II）和5,6-二氢-5-甲基菲啶（III）。通过D2O-CD3CN溶液的核磁共振光谱，观察到5,6-二氢-6-假基-5-甲基菲啶（IVb）（假碱）作为一种立即不稳定的产物。5-甲基菲啶铵碘（I）与甲氧基和乙氧基阴离子、吗啉、哌啶、吡咯烷、氰离子和丙酮反应生成相应的加合物。它们的结构由红外光谱、1H和13C核磁共振光谱确定。通过核磁共振光谱跟踪了5,6-二氢-5-甲基-6-吗啉基菲啶（VII）的反应。吗啉加合物VII在CD3CN-D2O溶液中生成假碱（IVb）和其不均化的产物：酮菲啶II和二氢菲啶III。将5,6-二氢-5-甲基-6-吗啉基菲啶（VII）与H2O / D2O在（CH3）2CO /（CD3）2CO中处理，分别形成CH3COCH2- / CD3COCD2-加合物XIa / XIb。
• Mass spectrometry of nitrogen heterocycles. 2. Correlation of mass spectrometric fragmentation processes and chemical aromatization reactions of dihydroazines
  作者：O. N. Chupakhin、V. G. Baklykov、N. A. Klyuev、A. I. Matern

  DOI：10.1007/bf00479610

  日期：1989.8
• Tinkler, Journal of the Chemical Society, 1906, vol. 89, p. 859
  作者：Tinkler

  DOI：——

  日期：——
• Dostal Ji, Potaek Milan, Nechvatal Miloslav, Collect. Czechosl. Chem. Commun., 58 (1993) N 2, S 395-403
  作者：Dostal Ji, Potaek Milan, Nechvatal Miloslav

  DOI：——

  日期：——
• Aurich, Hans Guenter; Deuschle, Eberhardt, Liebigs Annalen der Chemie, 1981, # 4, p. 719 - 733
  作者：Aurich, Hans Guenter、Deuschle, Eberhardt

  DOI：——

  日期：——