6-benzyl-5,6-dihydrophenanthridine | 16573-46-9

• 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: 6-benzyl-5,6-dihydrophenanthridine
• 英文别名: 6-Benzyl-5,6-dihydro-phenanthridin
• CAS: 16573-46-9
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: METMKZYRBZJFOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-benzyl-5,6-dihydrophenanthridine 在 过氧化氢苯甲酰 、 sodium dichromate 、 溶剂黄146 作用下， 反应 2.0h， 生成 6-benzoylphenanthridine N-oxide
  参考文献：
  名称：

  N-Alkoxyheterocycles As Irreversible Photooxidants

  摘要：

  AbstractIrreversible photooxidation based on N–O bond fragmentation is demonstrated for N‐methoxyheterocycles in both the singlet and triplet excited state manifolds. The energetic requirements for bond fragmentation are studied in detail. Bond fragmentation in the excited singlet manifold is possible for ππ* singlet states with energies significantly larger than the N–O bond dissociation energy of ca 55 kcal mol−1. For the nπ* triplet states, N–O bond fragmentation does not occur in the excited state for orbital overlap and energetic reasons. Irreversible photooxidation occurs in the singlet states by bond fragmentation followed by electron transfer. Irreversible photooxidation occurs in the triplet states via bimolecular electron transfer to the donor followed by bond fragmentation. Using these two sensitization schemes, donors can be irreversibly oxidized with oxidation potentials ranging from ca 1.6–2.2 V vs SCE. The corresponding N‐ethylheterocycles are characterized as conventional reversible photooxidants in their triplet states. The utility of these sensitizers is demonstrated by irreversibly generating the guanosine radical cation in buffered aqueous solution.

  DOI：

  10.1111/php.12227
• 作为产物：
  描述：

  菲啶 、 苄基氯化镁 在 乙醚 作用下， 生成 6-benzyl-5,6-dihydrophenanthridine
  参考文献：
  名称：

  Gilman; Eisch, Journal of the American Chemical Society, 1957, vol. 79, p. 4423,4425

  摘要：

  DOI：