β-hydroxy-N-(4-nitrophenyl)phenethylamine | 135286-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: β-hydroxy-N-(4-nitrophenyl)phenethylamine
• 英文别名: 2-((4-nitrophenyl)amino)-1-phenylethan-1-ol；2-[(4-Nitrophenyl)amino]-1-phenylethanol；2-(4-nitroanilino)-1-phenylethanol
• CAS: 135286-04-3
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: GQWAGTYGWKOUIB-UHFFFAOYSA-N

物化性质

• 沸点：
  439.3±24.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-hydroxy-N-(4-nitrophenyl)phenethylamine 在 sodium hydroxide 、 四丁基硫酸氢铵 、 对甲苯磺酰氯 作用下， 以 水 、 苯 为溶剂， 反应 0.5h， 以80%的产率得到N-(4-nitrophenyl)-2-phenyl-aziridine
  参考文献：
  名称：

  A FACILE SYNTHESIS OF N-ARYL AZIRIDINES

  摘要：

  Reaction of N-aryl-beta -amino alcohols with p-toluenesulphonyl chloride under phase transfer catalytic condition gave the corresponding N-aryl aziridines in good yields, whereas N-alkyl-beta -amino alcohol [for e.g., L-ephedrine] gave the corresponding N-tosyl derivative as the major product, along with the expected N-alkyl aziridines in lower yield.

  DOI：

  10.1081/scc-100103544
• 作为产物：
  描述：

  对硝基苯磺酰氯 在 ammonium hydroxide 、 sodium acetate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 β-hydroxy-N-(4-nitrophenyl)phenethylamine
  参考文献：
  名称：

  无金属β-氨基醇合成：两步微笑重排

  摘要：

  通过两步Smiles重排，在温和的反应条件下，已证明了在宽泛范围内合成β-氨基醇的新方法。此外，已经进行了理论计算以确认该机制的合理性。已经证明该方法对于N-芳基化的氨基醇特别有效，N-芳基化的氨基醇难以通过传统方法合成。

  DOI：

  10.1021/acs.joc.0c01543

文献信息

• Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate
  作者：Antonio Procopio、Marco Gaspari、Monica Nardi、Manuela Oliverio、Ornelio Rosati

  DOI：10.1016/j.tetlet.2008.02.010

  日期：2008.3

  Er(OTf)3 is proposed as a highly efficient and reusable catalyst for the opening of epoxides in water with aliphatic as well as aromatic amines leading to the synthesis of β-amino alcohols. The aqueous conditions employed in the present method will make it ‘environmentally friendly’ and potentially useful for industrial applications.

  提出了Er（OTf）3作为一种高效且可重复使用的催化剂，用于与脂肪族以及芳香族胺一起在水中打开环氧化物，从而导致β-氨基醇的合成。在本方法中采用的水性条件将使其“对环境友好”，并可能用于工业应用。
• Scandium triflate as an efficient and useful catalyst for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines under solvent-free conditions
  作者：Andrew T. Placzek、James L. Donelson、Rushi Trivedi、Richard A. Gibbs、Surya K. De

  DOI：10.1016/j.tetlet.2005.10.106

  日期：2005.12

  A simple and efficient method has been developed for the synthesis of P-amino alcohols by ring opening of epoxides in the presence of a catalytic amount of Sc(OTf)(3) at room temperature under solvent-free conditions. The reaction works well with both aromatic and aliphatic amines. High regio-, and diastereoselectivity can be considered as a noteworthy advantage of this method. (c) 2005 Elsevier Ltd. All rights reserved.
• Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxide
  作者：Marco Chini、Paolo Crotti、Franco Macchia

  DOI：10.1021/jo00020a042

  日期：1991.9
• Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines
  作者：Nianyuan Tan、Shuangfeng Yin、Yuefang Li、Renhua Qiu、Zhengong Meng、Xingxing Song、Shenglian Luo、Chak-Tong Au、Wai-Yeung Wong

  DOI：10.1016/j.jorganchem.2010.12.035

  日期：2011.4

  An air-stable organobismuth triflate complex with a novel 5,6,7,12-tetrahydrodibenzo[c,f]-[1,5]oxabismocine framework was synthesized and characterized by spectroscopic and single-crystal X-ray diffraction techniques. The organobismuth framework is cationic, and the complex shows relatively strong Lewis acidity (0.8 < H-o <= 3.3). It was found to exhibit high catalytic activity towards the ring-opening reaction of epoxides in aqueous media with aromatic amines at room temperature. This catalyst shows good stability, recyclability and reusability. The catalytic system affords a simple and efficient method for the synthesis of beta-amino alcohols. (C) 2011 Elsevier B. V. All rights reserved.
• Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement
  作者：Di Yang、Cai-Xia Xie、Xiao-Tian Wu、Luo-Ran Fei、Lei Feng、Chen Ma

  DOI：10.1021/acs.joc.0c01543

  日期：2020.12.4

  A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods

  通过两步Smiles重排，在温和的反应条件下，已证明了在宽泛范围内合成β-氨基醇的新方法。此外，已经进行了理论计算以确认该机制的合理性。已经证明该方法对于N-芳基化的氨基醇特别有效，N-芳基化的氨基醇难以通过传统方法合成。