N-(p-nitrophenyl)-2-anilonoethanol | 18226-18-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(p-nitrophenyl)-2-anilonoethanol
• 英文别名: <2-Hydroxy-aethyl>-<4-nitro-phenyl>-phenyl-amin；N-(ω-hydroxyethyl)-p-nitrodiphenylamine；2-[(4-Nitrophenyl)phenylamino]ethanol；2-(N-(4-nitrophenyl)anilino)ethanol
• CAS: 18226-18-1
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: DVRKLFIMNAJUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-(2-hydroxyethyl)-4-nitro-N-phenylbenzenesulfonamide 在 sodium hydroxide 作用下， 生成 N-(p-nitrophenyl)-2-anilonoethanol
  参考文献：
  名称：

  Kleb,K.G., Angewandte Chemie, 1968, vol. 80, p. 284 - 285

  摘要：

  DOI：

文献信息

• Photoinduced Intramolecular Aromatic Nucleophilic Substitution (the Photo-Smiles Rearrangement) in Amino Ethers
  作者：Kiyoshi Mutai、Keiji Kobayashi

  DOI：10.1246/bcsj.54.462

  日期：1981.2

  Intramolecular rearrangement was induced by light as well as base in a homologous series of 1-(p-nitrophenoxy)-ω-anilinoalkanes, p-O2NC6H4O(CH2)nNHPh(n=2–5), yielding N-(p-nitrophenyl)-ω-anilino-1-alkanols, p-O2NC6H4N(Ph)(CH2)nOH. The reaction rate in acetonitrile showed abnormal order, n=4>5>3>2, which was reversed by the addition of triethylamine. The mechanism of this photorearrangement through

  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)( )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。
• Spectroscopic and Kinetic Study of an Intramolecular Aromatic Nucleophilic Photosubstitution. Reaction Mechanism of a Photo-Smiles Rearrangement
  作者：Kenji Yokoyama、Ryoichi Nakagaki、Junko Nakamura、Kiyoshi Mutai、Saburo Nagakura

  DOI：10.1246/bcsj.53.2472

  日期：1980.9

  Photo-Smiles rearrangement reaction of N-[ω-(p-nitrophenoxy)alkyl]aniline was studied by measuring the absorption spectra of transient species. Two intermediates A and B were observed and were assigned to a solvated ion pair and the Meisenheimer complex, respectively. The reaction scheme, starting material→intramolecular charge transfer on excitation→A→B→final product, was derived from the relative

  通过测量瞬态物质的吸收光谱研究了 N-[ω-(对硝基苯氧基)烷基]苯胺的 Photo-Smiles 重排反应。观察到两种中间体 A 和 B，并分别分配给溶剂化离子对和 Meisenheimer 复合物。反应方案，起始材料→激发时分子内电荷转移→A→B→最终产物，源自A和B的相对产率和寿命，以及溶剂极性、三乙胺和氧的影响，以及每一步反应的烷基链长。
• 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.
• Competitive catalysis and quenching by amines of photo-Smiles rearrangement as evidence for a zwitterionic triplet as the proton-donating intermediate
  作者：Gene G. Wubbels、Bradley R. Sevetson、Houston Sanders

  DOI：10.1021/ja00185a034

  日期：1989.2
• Effect of α-cyclodextrin complexation on a general-base-catalyzed photo-smiles rearrangement
  作者：Gene G. Wubbels、Bradley R. Sevetson、Steven N. Kaganove

  DOI：10.1016/s0040-4039(00)84726-7

  日期：——