2-[(p-methoxyphenyl)amino]-1-propanol | 16955-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(p-methoxyphenyl)amino]-1-propanol
• 英文别名: 2-(4-methoxyphenylamino)propan-1-ol；2-(4-Methoxyanilino)propan-1-ol
• CAS: 16955-15-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: DYJPUIQQBCIFLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(p-methoxyphenyl)amino]-1-propanol 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-[(p-methoxyphenyl)(p-toluenesulfonyl)amino]propyl p-toluenesulfonate
  参考文献：
  名称：

  Aryl(sulfonyl)amino Group: A Convenient and Stable Yet Activated Modification of Amino Group for Its Intramolecular Displacement

  摘要：

  Aryl(sulfonyl)amino groups, readily derived from sulfonyl- or arylamines by standard methods as well as the recently introduced methods of sulfonylation and arylation, proved to be good leaving groups in intramolecular substitution reactions by various nitrogen, oxygen, and carbon nucleophiles.

  DOI：

  10.1021/ol101541p
• 作为产物：
  描述：

  甲醇 、 甲氧苯胺 、 乙醛 在 叔丁基过氧化氢 、 titanium(III) chloride 作用下， 反应 0.5h， 以65%的产率得到2-[(p-methoxyphenyl)amino]-1-propanol
  参考文献：
  名称：

  A New One-Pot, Four-Component Synthesis of 1,2-Amino Alcohols: TiCl₃/t-BuOOH-Mediated Radical Hydroxymethylation of Imines

  摘要：

  An amine, an aldehyde, and methanol can be readily assembled in one pot under very mild conditions through a free-radical multicomponent reaction by using an aqueous acidic TiCl3/t-BuOOH system to afford 1,2-amino alcohols in fair to excellent yields.

  DOI：

  10.1021/ol802244n

文献信息

• The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy)alkylanilines: the catalytic effect of phosphonium-based ionic liquids
  作者：Maurizio Selva、Massimo Fabris、Vittorio Lucchini、Alvise Perosa、Marco Noè

  DOI：10.1039/c0ob00105h

  日期：——

  At T ≥ 140 °C, different primary aromatic amines (pX–C6H4NH2; X = H, OCH3, CH3, Cl) react with both ethylene- and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl)anilines [pX–C6H4N(CH2CH(R)OH)2; R = H, CH3] are the major products and the competitive formation of carbamates is substantially ruled out. At 140 °C, under solventless conditions, the model reaction of aniline with ethylene carbonate goes to completion by simply mixing stoichiometric amounts of the reagents. However, a class of phosphonium ionic liquids (PILs) such as tetraalkylphosphonium halides and tosylates turn out to be active organocatalysts for both aniline and other primary aromatic amines. A kinetic analysis monitored by 13C NMR spectroscopy, shows that bromide exchanged PILs are the most efficient systems, able to impart a more than 8-fold acceleration to the reaction. The reactions of propylene carbonate take place at a higher temperature than those of ethylene carbonate, and only in the presence of PIL catalysts. A mechanism based on the Lewis acidity of tetraalkylphosphonium cations and the nucleophilicity of halide anions has been proposed to account for both the reaction chemoselectivity and the function of the catalysts.

  在T ≥ 140 °C时，不同的氨基芳烃（pX– H2；X = H, O , CH3, Cl）与乙烯碳酸酯和丙烯碳酸酯反应，产生了化学选择性的N-烷基化过程：双-N-(2-羟基烷基)苯胺[pX–C6H4N(CH2CH(R)OH)2；R = H, ]是主要产品，同时竞争性形成碳酸酯的可能性大大降低。在140 °C下，在无溶剂条件下，苯胺与乙烯碳酸酯的模型反应通过简单混合化学计量的反应物而达到完成。然而，一类磷阳离子液体（PILs），如四烷基磷铵卤化物和托烷基物，证明对苯胺和其他氨基芳烃均为活性有机催化剂。通过13C NMR光谱监测的动力学分析表明，溴化物交换的PILs是效率最高的系统，能使反应加速超过8倍。丙烯碳酸酯的反应发生在比乙烯碳酸酯更高的温度下，并且仅在PIL催化剂的存在下进行。已经提出了一种基于四烷基磷铵阳离子的路易斯酸性和卤离子的亲核性的机制，以解释反应的化学选择性和催化剂的功能。