N-(p-nitrophenyl)-5-anilino-1-pentanol | 67438-24-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(p-nitrophenyl)-5-anilino-1-pentanol
• 英文别名: 5-(N-(4-nitrophenyl)anilino)pentan-1-ol
• CAS: 67438-24-8
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: MPHRBBOPZZTDJT-UHFFFAOYSA-N

物化性质

• 沸点：
  489.2±30.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[5-(4-nitro-phenoxy)-pentyl]-aniline 以 乙腈 为溶剂， 以61%的产率得到N-(p-nitrophenyl)-5-anilino-1-pentanol
  参考文献：
  名称：

  氨基醚中的光致分子内芳香亲核取代（光微笑重排）

  摘要：

  在 1-(对硝基苯氧基)-ω-苯胺基烷烃 p-O2NC6H4O(CH2)nNHPh(n=2-5) 的同源系列中，光和碱诱导分子内重排，产生 N-(对硝基苯基) -ω-苯胺基-1-烷醇，p-O2NC6H4N(Ph)(CH2)nOH。乙腈中的反应速率呈异常顺序，n=4>5>3>2，加入三乙胺后反应相反。提出了通过自由基离子对和螺型迈森海默络合物进行光重排的机制。在此机理的基础上讨论了反应速率顺序的异常。

  DOI：

  10.1246/bcsj.54.462

文献信息

• Bifunctional reactivity of the nitrophenoxyl group in intramolecular photoreactions
  作者：Kiyoshi Mutai、Hideyuki Tukada、Ryoichi Nakagaki

  DOI：10.1021/jo00016a017

  日期：1991.8

  The photochemical behavior of a homologous series of compounds, p-O2NC6H4O(CH2)(n)NHPh (n = 2-10, 12, and 16) in acetonitrile is reported. The lower (n = 2-6) homologues undergo an apparently nucleophilic type rearrangement to give omega-((p-nitrophenyl)amino)alkanol, while the higher homologues (n greater-than-or-equal-to 8) undergo an intramolecular photoredox reaction accompanied by C-N bond cleavage to give omega-(p-nitrosophenoxy)alkanal and aniline. The n = 7 homologue is situated at the switching point of these two reaction pathways, exhibiting neither type of photoreactions. Photoinduced intramolecular electron transfer to generate a radical ion pair is observed for all homologues, and the quantum yield decreases with increasing chain length. This species is the intermediate in the photorearrangement, for which the effect of base-catalysis is discussed in connection with the reaction mechanism. Comparison of the quantum yield for the electron transfer in 1 with that in 1-(anilinomethyl)-4-((p-nitrophenoxy)methyl)cyclohexane reveals the dominance of through-bond electron-transfer mechanism in the higher (n greater-than-or-equal-to 6) homologues. The reaction quantum yield vs chain length profile is discussed in terms of the relative quantum yield of the radical ion pair, the chain conformation, and the photoredox reaction mechanism.
• MUTAI KIYOSHI; KOBAYASHI KEIJI, BULL. CHEM. SOC. JAP., 1981, 54, NO 2, 462-465
  作者：MUTAI KIYOSHI、 KOBAYASHI KEIJI

  DOI：——

  日期：——